Experimental study on the thermochemistry of some amino derivatives of uracil

International Nuclear Information System (INIS)

Ribeiro da Silva, Manuel A.V.; Amaral, Luisa M.P.F.; Szterner, Piotr

2011-01-01

Highlights: → Combustion calorimetry was used to determine Δ f H m 0 (cr) of amino derivatives of uracil. → Gas-phase Δ f H m 0 of amino derivatives of uracil have been derived. → The relative enthalpic stability of the title compounds is discussed in structural terms. - Abstract: Values of the standard (p 0 = 0.1 MPa) molar enthalpy of combustion, Δ c H m 0 , of four crystalline compounds: 5-aminouracil, 6-aminouracil, 6-amino-1-methyluracil, and 6-amino-1,3-dimethyluracil, were determined, at T = 298.15 K, using a static bomb combustion calorimeter. The values obtained of standard molar enthalpy of combustion were used to derive the standard molar enthalpy of formation of the compounds investigated in their condensed phase and together with literature values of the standard molar enthalpy of sublimation, yielded the standard molar enthalpies of formation in the gaseous phase. These are discussed in terms of the effects of the molecular structure on the relative enthalpic stability.

Mitochondrial proteomics of the acetic acid – induced programmed cell death response in a highly tolerant Zygosaccharomyces bailii – derived hybrid strain

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Joana F Guerreiro

2016-01-01

Full Text Available Very high concentrations of acetic acid at low pH induce programmed cell death (PCD in both the experimental model Saccharomyces cerevisiae and in Zygosaccharomyces bailii, the latter being considered the most problematic acidic food spoilage yeast due to its remarkable intrinsic resistance to this food preservative. However, while the mechanisms underlying S. cerevisiae PCD induced by acetic acid have been previously examined, the corresponding molecular players remain largely unknown in Z. bailii. Also, the reason why acetic acid concentrations known to be necrotic for S. cerevisiae induce PCD with an apoptotic phenotype in Z. bailii remains to be elucidated. In this study, a 2-DE-based expression mitochondrial proteomic analysis was explored to obtain new insights into the mechanisms involved in PCD in the Z. bailii derived hybrid strain ISA1307. This allowed the quantitative assessment of expression of protein species derived from each of the parental strains, with special emphasis on the processes taking place in the mitochondria known to play a key role in acetic acid – induced PCD. A marked decrease in the content of proteins involved in mitochondrial metabolism, in particular, in respiratory metabolism (Cor1, Rip1, Lpd1, Lat1 and Pdb1, with a concomitant increase in the abundance of proteins involved in fermentation (Pdc1, Ald4, Dld3 was registered. Other differentially expressed identified proteins also suggest the involvement of the oxidative stress response, protein translation, amino acid and nucleotide metabolism, among other processes, in the PCD response. Overall, the results strengthen the emerging concept of the importance of metabolic regulation of yeast PCD.

Free amino acids and sugars in the flower of Carthamus tinctorius L.

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Yoshiyuki Takahasi

2014-01-01

Full Text Available Qualitative and quantitative analyses of free amino acids and sugars in the extracts from freshly collected florets of Carthamus tinctorius L. were performed by combination of thin-layer chromatography (TLC, automatic amino acid analysis and gas-liquid chromatography (GLC. Sixteen amino acids were detected and their quantitative relations were investigated. Alditol acetate derivatives of free sugars were examined by GLC. The retention time and resolution pattern of the following monosaccharides, rhamnose, arabinose, xylose, mannose and glucose, were ultimately investigated.

Enantioselective conjugate addition of silylketene acetals to beta-enamidomalonates. Synthesis of beta-amino acid derivatives.

Science.gov (United States)

Sibi, Mukund P; Chen, Jianxie

2002-08-22

[reaction: see text] Conjugate addition of silylketene acetals or enolsilanes to enamidomalonates proceeds with excellent chemical efficiency and good selectivity using Cu(OTf)2 and a chiral bisoxazoline. The effect of the Lewis acid, ligand, the N-acyl substituent, and the nucleophile on yield and selectivity for the addition product have been evaluated.

Synthesis of 2-amino-4H-chromene derivatives under microwave ...

Indian Academy of Sciences (India)

ing method to construct the 2-amino-4H-chromene skeleton. 2. Experimental. 2.1 Materials and methods .... ing 2-amino-4H-chromene (3a–r) derivatives in good .... Students. Supplementary information. The electronic supporting information ...

Plant amino acid-derived vitamins: biosynthesis and function.

Science.gov (United States)

Miret, Javier A; Munné-Bosch, Sergi

2014-04-01

Vitamins are essential organic compounds for humans, having lost the ability to de novo synthesize them. Hence, they represent dietary requirements, which are covered by plants as the main dietary source of most vitamins (through food or livestock's feed). Most vitamins synthesized by plants present amino acids as precursors (B1, B2, B3, B5, B7, B9 and E) and are therefore linked to plant nitrogen metabolism. Amino acids play different roles in their biosynthesis and metabolism, either incorporated into the backbone of the vitamin or as amino, sulfur or one-carbon group donors. There is a high natural variation in vitamin contents in crops and its exploitation through breeding, metabolic engineering and agronomic practices can enhance their nutritional quality. While the underlying biochemical roles of vitamins as cosubstrates or cofactors are usually common for most eukaryotes, the impact of vitamins B and E in metabolism and physiology can be quite different on plants and animals. Here, we first aim at giving an overview of the biosynthesis of amino acid-derived vitamins in plants, with a particular focus on how this knowledge can be exploited to increase vitamin contents in crops. Second, we will focus on the functions of these vitamins in both plants and animals (and humans in particular), to unravel common and specific roles for vitamins in evolutionary distant organisms, in which these amino acid-derived vitamins play, however, an essential role.

Selective Hydrogenolysis of Furfural Derivative 2-Methyltetrahydrofuran into Pentanediol Acetate and Pentanol Acetate over Pd/C and Sc(OTf)3 Cocatalytic System.

Science.gov (United States)

Zhang, Kun; Li, Xing-Long; Chen, Shi-Yan; Xu, Hua-Jian; Deng, Jin; Fu, Yao

2018-02-22

It is of great significance to convert platform molecules and their derivatives into high value-added alcohols, which have multitudinous applications. This study concerns systematic conversion of 2-methyltetrahydrofuran (MTHF), which is obtained from furfural, into 1-pentanol acetate (PA) and 1,4-pentanediol acetate (PDA). Reaction parameters, such as the Lewis acid species, reaction temperature, and hydrogen pressure, were investigated in detail. 1 H NMR spectroscopy and reaction dynamics study were also conducted to help clarify the reaction mechanism. Results suggested that cleavage of the primary alcohol acetate was less facile than that of the secondary alcohol acetate, with the main product being PA. A PA yield of 91.8 % (150 °C, 3 MPa H 2 , 30 min) was achieved by using Pd/C and Sc(OTf) 3 as a cocatalytic system and an 82 % yield of PDA was achieved (150 °C, 30 min) by using Sc(OTf) 3 catalyst. Simultaneously, the efficient conversion of acetic esters into alcohols by simple saponification was carried out and led to a good yield. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis and radioprotective study of novel amino-alkyl dithiocarbamic acid derivatives against γ-irradiation in mice

International Nuclear Information System (INIS)

Hosseinimehr, S. J.; Beiki, D.; Kebriaeezadeh, A.; Khalaj, A.; Pirali Hamedani, M.; Akhlaghpoor, S.; Esmaeili, H.; Barazesh, A. R.

2009-01-01

The aim of this study was to evaluate the radioprotective capacity of some novel amino alkylated dithiocarbamic acid potassium salts against γ-irradiation in mice. Materials and Methods: Eight compounds containing 2-aminoethyl-, 3-aminopropyl-, 4-aminobutyl-, 5-aminopentyl-, 6-aminohexyl-, 7-amino heptyl-, 8-amino octyl and 9-amino nonyl of dithiocarbamate derivatives were prepared. Male NMRI mice were injected intraperitoneally with a geometric progression of doses (300 -1000 mg/kg), through the dose response range for lethal toxicity. To evaluate the radioprotective activity, one-half of the toxic LD 50 of each compound were injected intraperitoneally to groups of twenty mice, 30 minutes prior to γ-irradiation. The treated animals were kept for 30 days, and the lethality was recorded each day. Results: Among Eight compounds of alkyl dithiocarbamic acid derivatives, 5-aminopentyl, 7-amino heptyl, 8-amino octyl and 9-amino nonyl dithiocarbamic acid mono potassium salts are new compounds. All evaluated compounds showed a concentration dependent effect on the survival in mice. The LD 50 values were found to be more than 599 mg/kg. The percentages of 30-day survival of mice for 2-aminoethyl, 7-amino heptyl and 8-amino octyl dithiocarbamic acid derivatives were 7%, 40% and 13.5%, respectively, when injected 30 minutes before γ-irradiation. Other compounds had no radioprotective effects. Statistical analysis showed a significant difference between the treated and control groups for the 7-amino heptyl derivative (p<0.05). Conclusion: Among the compounds investigated in this study, 7-amino heptyl dithiocarbamate derivative showed more radioprotective effects in comparison with the others. Although it seems that the radioprotective effects in these derivatives correlate with the size of the alkyl chain, more experiments are required to support this hypothesis.

Catalytic amino acid production from biomass-derived intermediates

KAUST Repository

Deng, Weiping

2018-04-30

Amino acids are the building blocks for protein biosynthesis and find use in myriad industrial applications including in food for humans, in animal feed, and as precursors for bio-based plastics, among others. However, the development of efficient chemical methods to convert abundant and renewable feedstocks into amino acids has been largely unsuccessful to date. To that end, here we report a heterogeneous catalyst that directly transforms lignocellulosic biomass-derived α-hydroxyl acids into α-amino acids, including alanine, leucine, valine, aspartic acid, and phenylalanine in high yields. The reaction follows a dehydrogenation-reductive amination pathway, with dehydrogenation as the rate-determining step. Ruthenium nanoparticles supported on carbon nanotubes (Ru/CNT) exhibit exceptional efficiency compared with catalysts based on other metals, due to the unique, reversible enhancement effect of NH3 on Ru in dehydrogenation. Based on the catalytic system, a two-step chemical process was designed to convert glucose into alanine in 43% yield, comparable with the well-established microbial cultivation process, and therefore, the present strategy enables a route for the production of amino acids from renewable feedstocks. Moreover, a conceptual process design employing membrane distillation to facilitate product purification is proposed and validated. Overall, this study offers a rapid and potentially more efficient chemical method to produce amino acids from woody biomass components.

Synthesis and pharmacology of N-alkylated derivatives of the excitotoxin ibotenic acid

DEFF Research Database (Denmark)

Madsen, U; Dumpis, M A; Bräuner-Osborne, Hans

1998-01-01

Three amino-alkylated derivatives of the naturally occurring excitatory amino acid (EAA) receptor agonist ibotenic acid (Ibo) have been synthesized and tested pharmacologically. N-Methyl-Ibo (1a) and N-ethyl-Ibo (1b) were shown to be agonists at NMDA receptors (EC50 = 140 and 320 micro......-c and the potent NMDA agonist 2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic acid (AMAA) in order to elucidate the observed structure-activity data....

Docking of oxalyl aryl amino benzoic acid derivatives into PTP1B

Science.gov (United States)

Verma, Neelam; Mittal, Minakshi; Verma, Raman kumar

2008-01-01

Protein Tyrosine Phosphatases (PTPs) that function as negative regulators of the insulin signaling cascade have been identified as novel targets for the therapeutic enhancement of insulin action in insulin resistant disease states. Reducing Protein Tyrosine Phosphatase1B (PTP1B) abundance not only enhances insulin sensitivity and improves glucose metabolism but also protects against obesity induced by high fat feeding. PTP1B inhibitors such as Formylchromone derivatives, 1, 2-Naphthoquinone derivatives and Oxalyl aryl amino benzoic derivatives may eventually find an important clinical role as insulin sensitizers in the management of Type-II Diabetes and metabolic syndrome. We have carried out docking of modified oxalyl aryl amino benzoic acid derivatives into three dimensional structure of PTP1B using BioMed CAChe 6.1. These compounds exhibit good selectivity for PTP1B over most of phosphatases in selectivity panel such as SHP-2, LAR, CD45 and TCPTP found in literature. This series of compounds identified the amino acid residues such as Gly220 and Arg221 are important for achieving specificity via H-bonding interactions. Lipophilic side chain of methionine in modified oxalyl aryl amino benzoic acid derivative [1b (a2, b2, c1, d)] lies in closer vicinity of hydrophobic region of protein consisted of Meth258 and Phe52 in comparison to active ligand. Docking Score in [1b (a2, b2, c1, d)] is -131.740Kcal/mol much better than active ligand score -98.584Kcal/mol. This information can be exploited to design PTP1B specific inhibitors. PMID:19238234

Spin labeled amino acid nitrosourea derivatives--synthesis and antitumour activity.

Science.gov (United States)

Zheleva, A; Raikov, Z; Ilarionova, M; Todorov, D

1995-01-01

The synthesis of three spin labeled derivatives of N-[N'-(chloroethyl)-N'-nitrosocarbamoyl] amino acids is reported. The new nitrosoureas are obtained by condensation of the corresponding N-[N'-(2-chloroethyl)-N'-nitrosocarbamoyl] amino acid with 2,2,6,6-tetramethyl-1-oxyl-4-aminopiperidine using dicyclohexylcarbodiimide. Their chemical structures are confirmed by elemental analysis, IR, MS, and EPR spectroscopy. All newly synthesized compounds showed high antitumour activity against the lymphoid leukemia L1210 in BDF1 mice.

Acetate supplementation induces growth arrest of NG2/PDGFRα-positive oligodendroglioma-derived tumor-initiating cells.

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Patrick M Long

Full Text Available Cancer is associated with globally hypoacetylated chromatin and considerable attention has recently been focused on epigenetic therapies. N-acetyl-L-aspartate (NAA, the primary storage form of acetate in the brain, and aspartoacylase (ASPA, the enzyme responsible for NAA catalysis to generate acetate and ultimately acetyl-Coenzyme A for histone acetylation, are reduced in oligodendroglioma. The short chain triglyceride glyceryl triacetate (GTA, which increases histone acetylation and inhibits histone deacetylase expression, has been safely used for acetate supplementation in Canavan disease, a leukodystrophy due to ASPA mutation. We demonstrate that GTA induces cytostatic G0 growth arrest of oligodendroglioma-derived cells in vitro, without affecting normal cells. Sodium acetate, at doses comparable to that generated by complete GTA catalysis, but not glycerol also promoted growth arrest, whereas long chain triglycerides promoted cell growth. To begin to elucidate its mechanism of action, the effects of GTA on ASPA and acetyl-CoA synthetase protein levels and differentiation of established human oligodendroglioma cells (HOG and Hs683 and primary tumor-derived oligodendroglioma cells that exhibit some features of cancer stem cells (grade II OG33 and grade III OG35 relative to an oligodendrocyte progenitor line (Oli-Neu were examined. The nuclear localization of ASPA and acetyl-CoA synthetase-1 in untreated cells was regulated during the cell cycle. GTA-mediated growth arrest was not associated with apoptosis or differentiation, but increased expression of acetylated proteins. Thus, GTA-mediated acetate supplementation may provide a safe, novel epigenetic therapy to reduce the growth of oligodendroglioma cells without affecting normal neural stem or oligodendrocyte progenitor cell proliferation or differentiation.

Synthesis and Antifungal Activity of Azetidinone and Thiazolidinones Derivatives of 2-Amino-6-(2-naphthalenylthiazolo[3,2-d]thiadiazole

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K. H. Patel

2006-01-01

Full Text Available 2-Amino-6-(2-naphthalenylthiazolo[3,2-d]thiadiazole [1] was prepared by treatment of KCNS and Br2 on 2-Amino-4-(2-naphthalenyl thiazole. This amine on facile condensation with aromatic aldehydes afford Schiff Base/anils/azomethines(2a-h. These anils on cyclocondensation reaction with chloro acetyl chloride and thio glycolic acid (i.e. mercapto acetic acid afford 2-azetidinones and 4-thiazolidinones respectively. The prepared compounds have been screened on some stains of fungai.

Utilization of acidic α-amino acids as acyl donors: an effective stereo-controllable synthesis of aryl-keto α-amino acids and their derivatives.

Science.gov (United States)

Wang, Lei; Murai, Yuta; Yoshida, Takuma; Okamoto, Masashi; Tachrim, Zetryana Puteri; Hashidoko, Yasuyuki; Hashimoto, Makoto

2014-05-16

Aryl-keto-containing α-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl α-amino acids, nonproteinogenic α-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing α-amino acids by Friedel-Crafts acylation using acidic α-amino acids as acyl-donors and Lewis acids or Brönsted acids as catalysts.

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

KAUST Repository

Fava, Eleonora; Millet, Anthony; Nakajima, Masaki; Loescher, Sebastian; Rueping, Magnus

2016-01-01

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

KAUST Repository

Fava, Eleonora

2016-05-02

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.

Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline.

Science.gov (United States)

Ulbrich, Dirk; Daniliuc, Constantin G; Haufe, Günter

2016-03-07

Intending to synthesize ω,ω-difluoroalkyl amino acid derivatives by oxidative desulfurization-fluorination reactions of suitable arylthio-2-phthalimido butanoates and pentanoates, in addition to small amounts of the target products, mainly α,ω-polyfluorinated amino acid derivatives were formed by additional sulfur-assisted α-fluorination. This novel structural motif was verified spectroscopically as well as by X-ray analysis. A plausible mechanism of formation is suggested. Using a different approach, δ,δ-difluoronorvaline hydrochloride was synthesized with at least 36% enantiomeric excess via deoxofluorination of the corresponding aldehyde.

An easy and efficient method to produce {gamma}-amino alcohols by reduction of {beta}-enamino ketones

Energy Technology Data Exchange (ETDEWEB)

Harris, Maria Ines N.C.; Braga, Antonio C.H. [Universidade Estadual de Campinas, SP (Brazil). Inst. de Quimica]. E-mail: herrera@iqm.unicamp.br

2004-12-01

Reduction of {beta}-enamino ketones 2 with NaBH{sub 4} in glacial acetic acid gave {gamma}-amino alcohols 1 in 70% to 98% yield with diastereomeric excesses, preferentially the syn product, from 44% to 90%. The stereochemistry of these compounds was confirmed by analysis of their tetrahydro-1,3-oxazine derivatives 3. (author)

Hydrogen/deuterium exchange of cross-linkable alpha-amino acid derivatives in deuterated triflic acid

OpenAIRE

Wang, Lei; Murai, Yuta; Yoshida, Takuma; Okamoto, Masashi; Masuda, Katsuyoshi; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hatanaka, Yasumaru; Hashimoto, Makoto

2014-01-01

In this paper we report here a hydrogen/deuterium exchange (H/D exchange) of cross-linkable alpha-amino acid derivatives with deuterated trifluoromethanesulfonic acid (TfOD). H/D exchange with TfOD was easily applied to o-catechol containing phenylalanine (DOPA) within an hour. A partial H/D exchange was observed for trifluoromethyldiazirinyl (TFMD) phenylalanine derivatives. N-Acetyl-protected natural aromatic alpha-amino acids (Tyr and Trp) were more effective in H/D exchange than unprotect...

Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl] acetic acids, 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]propionic acids and related derivatives.

Science.gov (United States)

Al-Deeb, Omar A; Al-Omar, Mohamed A; El-Brollosy, Nasser R; Habib, Elsayed E; Ibrahim, Tarek M; El-Emam, Ali A

2006-01-01

The reaction of 3-(1-adamantyl)-4-substituted-1,2,4-triazoline-5-thiones 3a-g with sodium chloroacetate, in ethanolic sodium hydroxide yielded the corresponding N1-acetic acid derivatives 4a-g. The interaction of 3a-g with ethyl 2-bromopropionate in acetone, in the presence of potassium carbonate, yielded the corresponding N1-ethyl propionate derivatives 5a-g, which upon hydrolysis with aqueous sodium hydroxide afforded the corresponding propionic acid derivatives 6a-g. Similarly, the reaction of 3-(1-adamantyl)-4-amino-1,2,4-triazoline-5-thione 7 with sodium chloroacetate in ethanolic sodium hydroxide yielded the corresponding N1-acetic acid derivative 8. On the other hand, the reaction of 2-(1-adamantyl)-1,3,4-oxadiazoline-5-thione 9 with sodium chloroacetate yielded the corresponding S-acetic acid derivative 10. Compounds 4a-g, 5b, 5c, 5g, 6a-g, 8 and 10 were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives produced good or moderate activities particularly against Bacillus subtilis. In addition, the in vivo anti-inflammatory activities of these compounds were determined using the carrageenin-induced paw oedema method in rats. Compounds 4a, 4b, 4e, 4f, 6f, 6g and 10 produced good dose-dependent anti-inflammatory activities.

Effect of benzyl amino purine and indole-3-acetic acid on propagation of Sterculia foetida in vitro

Science.gov (United States)

Yuniastuti, E.; Widodo, C. E.; Samanhudi; Delfianti, M. N. I.

2018-03-01

Sterculia foetida is an oval seed plants that can be used as biofuel, which is one of the environmental friendly fuels. This plant is quite hard to find because not many peoples cultivate the plants. An in vitro propagation is one way to preserve the plant. This research aimed to determine optimum concentration of benzyl amino purine (BAP) and indole-3-acetic acid (IAA) to propagate S. foetida in vitro. The results showed that woody plant medium (WPM) added by 4 mg L BAP-1 and 0.5 mg L IAA-1 was able to produce complete plantlet, whereas those added by 4 mg L BAP-1 and 1 mg L IAA-1 generated the best growth of shoot and leaves.

Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives

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E. K. Mikhalchenko

2017-04-01

Full Text Available Introduction. Heterocyclic compounds play an important role in the metabolic processes of human organism. Structures of vitamins, nucleotides, chromoproteins are based on Nitrogen-containing heterocycles (purine, pyrimidine, thiazole etc. Thus, it was obvious to use these organic substances as basic molecules for synthetic research of biologically active compounds which could be used for treatment of different pathological processes. In their research, some scientist pay special attention to xanthine derivatives that are well-known low toxic natural compounds with wide spectrum of pronounced pharmacological properties (antioxidant, diuretic, antibacterial, anti-inflammatory etc. Insertion of carboxyl group in the structure of xanthine molecule is a prospective ability of its synthetic potential increasing. Aim of our research was the development of method of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives synthesis and studying their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M. 1Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian», USA solvent – (DMSO-d6, internal standard – ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Results and discussion. We selected 3-benzyl-8-propyl xanthine as initial compound for our study. By its interaction with chloroacetic acid, chloroacetamide or propyl chloroacetate in DMF in the presence of calculated amount of NaHCO3 we synthesized 3-benzyl-8-propylxanthinyl-7-acetic acid its ester and amide. At the same time we found that obtaining of xanthinyl-7-acetic acid by hydrolysis of its ester produced with higher yield. On the next stage of our research we synthesized a number of water-soluble salts of 3-benzyl-8-propylxanthinyl-7-acetic acid by reaction of acid with different primary and secondary amines. The structures of all obtained compounds were

One-Pot Synthesis of Novel Chiral β-Amino Acid Derivatives by Enantioselective Mannich Reactions Catalyzed by Squaramide Cinchona Alkaloids

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Kankan Zhang

2013-05-01

Full Text Available An efficient one-pot synthesis of novel β-amino acid derivatives containing a thiadiazole moiety was developed using a chiral squaramide cinchona alkaloid as organocatalyst. The reactions afforded chiral β-amino acid derivatives in moderate yields and with moderate to excellent enantioselectivities. The present study demonstrated for the first time the use of a Mannich reaction catalyzed by a chiral bifunctional organocatalyst for the one-pot synthesis of novel β-amino acid derivatives bearing a 1,3,4-thiadiazole moiety on nitrogen.

Detoxification of biomass derived acetate via metabolic conversion to ethanol, acetone, isopropanol, or ethyl acetate

Science.gov (United States)

Sillers, William Ryan; Van Dijken, Hans; Licht, Steve; Shaw, IV, Arthur J.; Gilbert, Alan Benjamin; Argyros, Aaron; Froehlich, Allan C.; McBride, John E.; Xu, Haowen; Hogsett, David A.; Rajgarhia, Vineet B.

2017-03-28

One aspect of the invention relates to a genetically modified thermophilic or mesophilic microorganism, wherein a first native gene is partially, substantially, or completely deleted, silenced, inactivated, or down-regulated, which first native gene encodes a first native enzyme involved in the metabolic production of an organic acid or a salt thereof, thereby increasing the native ability of said thermophilic or mesophilic microorganism to produce lactate or acetate as a fermentation product. In certain embodiments, the aforementioned microorganism further comprises a first non-native gene, which first non-native gene encodes a first non-native enzyme involved in the metabolic production of lactate or acetate. Another aspect of the invention relates to a process for converting lignocellulosic biomass to lactate or acetate, comprising contacting lignocellulosic biomass with a genetically modified thermophilic or mesophilic microorganism.

Human HDAC isoform selectivity achieved via exploitation of the acetate release channel with structurally unique small molecule inhibitors

Energy Technology Data Exchange (ETDEWEB)

Whitehead, Lewis; Dobler, Markus R.; Radetich, Branko; Zhu, Yanyi; Atadja, Peter W.; Claiborne, Tavina; Grob, Jonathan E.; McRiner, Andrew; Pancost, Margaret R.; Patnaik, Anup; Shao, Wenlin; Shultz, Michael; Tichkule, Ritesh; Tommasi, Ruben A.; Vash, Brian; Wang, Ping; Stams, Travis (Novartis)

2013-11-20

Herein we report the discovery of a family of novel yet simple, amino-acid derived class I HDAC inhibitors that demonstrate isoform selectivity via access to the internal acetate release channel. Isoform selectivity criteria is discussed on the basis of X-ray crystallography and molecular modeling of these novel inhibitors bound to HDAC8, potentially revealing insights into the mechanism of enzymatic function through novel structural features revealed at the atomic level.

Synthesis and physical-chemical properties of functional derivatives of 3-benzyl-8-propylxanthinyl-7-acetic acid

Directory of Open Access Journals (Sweden)

E. K. Mikhal’chenko

2017-08-01

Full Text Available Introduction. Synthetic research of new biologically active compounds occupies an important place in modern pharmaceutical science.Thus it is important to develop techniques for the biologically active substances functionalization. Esters and amides take special place among the variety of functional derivatives of organic acids,. These fragments are well-known pharmacophores and could be found in a wide range of drugs. Thus, the nootropic agent pyracetam is 2-oxo-1-pyrolidineacetamide, and is the selective antagonist of β-adrenoreceptores; atenolol is a derivative of benzeneacetamide. Substituted acetamide and ester fragments are also present in the structures of aprofen, spasmolitin, acetylidine and β-lactam cephalosporins and penicillins antibiotics.Aim of our research was the synthetic method development for functional derivatives of 3-benzyl-8-propylxanthinyl-7-acetic acid and the study of their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M. 1Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian» – USA solvent – (DMSO-d6, internal standard – ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Chemical shifts were reported in ppm (parts per million values. Infrared (IR spectra were measured on a Bruker Alpha instrument using a potassium bromide (KBr disk, scanning from 400 to 4000 cm-1. Results and discussion. We selected 3-benzyl-8-propylxanthinyl-7-acetic acid as initial compound for our study. For synthesis of hexyl, heptyl, octyl, nonyl, decyl and benzyl esters of 3-benzyl-8-propylxanthinyl-7-acetic acid we used alternative method, that included alkylation of sodium salts of acids with alkyl halogens. Reaction was made at DMF medium by reflux of reagents. Next stage of our research was the synthesis of amides of 3-beznyl-8-propylxanthinyl-7-acetic acid by the reaction of ethyl or propyl esters

Amino acid derivatives of 5-ASA as novel prodrugs for intestinal drug delivery.

Science.gov (United States)

Clerici, C; Gentili, G; Boschetti, E; Santucci, C; Aburbeh, A G; Natalini, B; Pellicciari, R; Morelli, A

1994-12-01

In an attempt to obtain site-specific delivery of 5-ASA in the intestinal tract, we have determined the extent of absorption and metabolism of a number of novel 5-ASA derivatives, namely, (N-L-glutamyl)-amino-2-salicylic acid (1), (N-L-aspartyl)-amino-2-salicylic-acid (2), 5-aminosalicyl-L-proline-L-leucine (3), and 5-(N-L-glutamyl)-aminosalicyl-L-proline-L-leucine (4), which are selectively cleaved by intestinal brush border aminopeptidase A and carboxypeptidases. These novel prodrugs, 5-ASA, and sulfasalazine were administered to adult Fisher rats (N = 30) and to animals that had undergone prior colostomy (N = 30). Urine and feces were collected at timed intervals for 48 hr and the metabolites, 5-ASA, and N-acetyl-5-ASA were measured by high-performance liquid chromatography. The absorption and metabolism of all compounds were essentially identical in colostomized and normal animals. 5-ASA exhibited a rapid proximal intestinal absorption as evidenced by the high cumulative urinary excretion (> 65%) and low fecal excretion. Sulfasalazine, as expected, exhibited a lower urinary recovery (metabolite. The novel glutamate and aspartate derivatives (1 and 2) behaved similarly to sulfasalazine, while administration of the proline-leucine derivative (3) resulted in urinary and fecal recovery values intermediate with respect to those observed with 5-ASA and sulfasalazine. 5-(N-L-Glutamyl)-aminosalicyl-L-proline-L-leucine yielded the highest fecal recovery of 5-ASA and its N-acetyl derivative, indicating a more efficient delivery to the distal bowel. Amino acid derivatives of 5-ASA appear to be potentially useful prodrugs for the site-specific delivery of 5-ASA to different regions of the intestinal tract.

Amino acidis derived from Titan tholins

Science.gov (United States)

Khare, Bishun N.; Sagan, Carl; Ogino, Hiroshi; Nagy, Bartholomew; Er, Cevat

1986-01-01

The production of amino acids by acid treatment of Titan tholin is experimentally investigated. The synthesis of Titan tholin and the derivatization of amino acids to N-trifluoroacetyl isopropyl esters are described. The gas chromatography/mass spectroscopy analysis of the Titan tholins reveals the presence of glycine, alpha and beta alainine, and aspartic acid, and the total yield of amino acids is about 0.01.

Amino acid derivatives are substrates or non-transported inhibitors of the amino acid transporter PAT2 (slc36a2).

Science.gov (United States)

Edwards, Noel; Anderson, Catriona M H; Gatfield, Kelly M; Jevons, Mark P; Ganapathy, Vadivel; Thwaites, David T

2011-01-01

The H(+)-coupled amino acid transporter PAT2 (SLC36A2) transports the amino acids proline, glycine, alanine and hydroxyproline. A physiological role played by PAT2 in amino acid reabsorption in the renal proximal tubule is demonstrated by mutations in SLC36A2 that lead to an iminoglycinuric phenotype (imino acid and glycine uria) in humans. A number of proline, GABA and tryptophan derivatives were examined to determine if they function either as transported substrates or non-transported inhibitors of PAT2. The compounds were investigated following heterologous expression of rat PAT2 in Xenopus laevis oocytes. PAT2 function was characterised by: radiotracer uptake and competition (cis-inhibition) studies; radiotracer efflux and trans-stimulation; and measurement of substrate-induced positive inward current by two-electrode voltage-clamp. In general, the proline derivatives appeared to be transported substrates and the relative ability to induce current flow was closely related to the inhibitory effects on PAT2-mediated l-[(3)H]proline uptake. In contrast, certain heterocyclic GABA derivatives (e.g. l-pipecolic acid) were translocated only slowly. Finally, the tryptophan derivatives inhibited PAT2 function but did not undergo transport. l-Proline uptake was inhibited by 5-hydroxy-l-tryptophan (IC(50) 1.6±0.4mM), α-methyl-d,l-tryptophan (3.5±1.5mM), l-tryptophan, 1-methyl-l-tryptophan and indole-3-propionic acid. Although neither 5-hydroxy-l-tryptophan nor α-methyl-d,l-tryptophan were able to elicit inward current in PAT2-expressing oocytes both reduced the current evoked by l-proline. 5-Hydroxy-l-tryptophan and α-methyl-d,l-tryptophan were unable to trans-stimulate l-proline efflux from PAT2-expressing oocytes, confirming that the two compounds act as non-transported blockers of PAT2. These two tryptophan derivatives should prove valuable experimental tools in future investigations of the physiological roles of PAT2. Copyright © 2010 Elsevier B.V. All rights

Synthesis and evaluation of fluorine-substituted phenyl acetate derivatives as ultra-short recovery sedative/hypnotic agents.

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Heng Zhang

Full Text Available BACKGROUND: Soft drugs are molecules that are purposefully designed to be rapidly metabolized (metabolically labile. In anesthesia, the soft drug is useful because it enables precise titration to effect and rapid recovery, which might allow swift and clear-headed recovery of consciousness and early home readiness. Propofol may cause delayed awakening after prolonged infusion. Propanidid and AZD3043 have a different metabolic pathway compared to propofol, resulting in a short-acting clinical profile. Fluorine imparts a variety of properties to certain medicines, including an enhanced absorption rate and improved drug transport across the blood-brain barrier. We hypothesized that the introduction of fluorine to the frame structure of propanidid and AZD3043 would further accelerate the swift and clear-headed recovery of consciousness. To test this hypothesis, we developed a series of fluorine-containing phenyl acetate derivatives. METHODOLOGY/PRINCIPAL FINDINGS: Fluorine-containing phenyl acetate derivatives were synthesized, and their hypnotic potencies and durations of LORR following bolus or infusion administration were determined in mice, rats and rabbits. The metabolic half-lives in the blood of various species were determined chromatographically. In vitro radioligand binding and γ-aminobutyric acidA (GABAA receptor electrophysiology studies were performed. Among the 12 synthesized fluorine-containing phenyl acetate derivatives, compound 5j induced comparable duration of LORR with AZD3043, but more rapid recovery than AZD3043, propanidid and propofol. The time of compound 5j to return to walk and behavioral recovery are approximately reduced by more than 50% compared to AZD3043 in mice and rats and rabbits. The HD50 of compound 5j decreased with increasing animal size. CONCLUSIONS/SIGNIFICANCE: The rapid recovery might make compound 5j suitable for precise titration and allow swift and clear-headed recovery of consciousness and early home

Stereoselective synthesis of functionalized cyclic amino acid derivatives via a [2,3]-Stevens rearrangement and ring-closing metathesis.

Science.gov (United States)

Nash, Aaron; Soheili, Arash; Tambar, Uttam K

2013-09-20

Unnatural cyclic amino acids are valuable tools in biomedical research and drug discovery. A two-step stereoselective strategy for converting simple glycine-derived aminoesters into unnatural cyclic amino acid derivatives has been developed. The process includes a palladium-catalyzed tandem allylic amination/[2,3]-Stevens rearrangement followed by a ruthenium-catalyzed ring-closing metathesis. The [2,3]-rearrangement proceeds with high diastereoselectivity through an exo transition state. Oppolzer's chiral auxiliary was utilized to access an enantiopure cyclic amino acid by this approach, which will enable future biological applications.

Study of antileishmanial activity of 2-aminobenzoyl amino acid hydrazides and their quinazoline derivatives.

Science.gov (United States)

Khattab, Sherine Nabil; Haiba, Nesreen Saied; Asal, Ahmed Mosaad; Bekhit, Adnan A; Guemei, Aida A; Amer, Adel; El-Faham, Ayman

2017-02-15

A new small library of 2-aminobenzoyl amino acid hydrazide derivatives and quinazolinones derivatives was synthesized and fully characterized by IR, NMR, and elemental analysis. The activity of the prepared compounds on the growth of Leishmania aethiopica promastigotes was evaluated. 2-Benzoyl amino acid hydrazide showed higher inhibitory effect than the quinazoline counterpart. The in vitro antipromastigote activity demonstrated that compounds 2a, 2b, 2f and 4a had IC 50 better than standard drug miltefosine and comparable activity to amphotericin B deoxycholate, which indicates their high antileishmanial activity against Leishmania. aethiopica. Among the prepared compounds; 2-amino-N-(6-hydrazinyl-6-oxohexyl)benzamide 2f (IC 50 =0.051μM) has the best activity, 154 folds more active than reference standard drug miltefosine (IC 50 =7.832μM), and half fold the activity of amphotericin B (IC 50 =0.035μM). In addition, this compound was safe and well tolerated by experimental animals orally up to 250mg/kg and parenterally up to 100mg/kg. Copyright © 2017 Elsevier Ltd. All rights reserved.

GAS-PHASE SYNTHESIS OF PRECURSORS OF INTERSTELLAR GLYCINE: A COMPUTATIONAL STUDY OF THE REACTIONS OF ACETIC ACID WITH HYDROXYLAMINE AND ITS IONIZED AND PROTONATED DERIVATIVES

Energy Technology Data Exchange (ETDEWEB)

Barrientos, Carmen; Redondo, Pilar; Largo, Laura; Rayon, Victor M.; Largo, Antonio, E-mail: alargo@qf.uva.es [Departamento de Quimica Fisica y Quimica Inorganica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid (Spain)

2012-04-01

A computational study of the reactions of hydroxylamine and its ionized and protonated derivatives with acetic acid is provided. The reaction of neutral hydroxylamine with acetic acid, despite being clearly exothermic, involves a very large energy barrier. The reaction of ionized hydroxylamine with acetic acid is also clearly exothermic, but again a significant energy barrier is found (around 24 kcal mol{sup -1} at the CCSD(T) level). The reaction of the most stable protonated isomer of hydroxylamine, NH{sub 3}OH{sup +}, with acetic acid also involves a high barrier (more than 27 kcal mol{sup -1} at the CCSD(T) level). Only the higher energy isomer, NH{sub 2}OH{sup +}{sub 2}, leads to a sensibly lower energy barrier (about 2.3 kcal mol{sup -1} at the CCSD(T) level). Nevertheless, an estimate of the reaction coefficient at low temperatures such as those reigning in the interstellar medium gives very low values. Therefore, it seems that precursors of interstellar glycine could not be efficiently produced from the reactions of hydroxylamine-derived ions with acetic acid.

GAS-PHASE SYNTHESIS OF PRECURSORS OF INTERSTELLAR GLYCINE: A COMPUTATIONAL STUDY OF THE REACTIONS OF ACETIC ACID WITH HYDROXYLAMINE AND ITS IONIZED AND PROTONATED DERIVATIVES

International Nuclear Information System (INIS)

Barrientos, Carmen; Redondo, Pilar; Largo, Laura; Rayón, Víctor M.; Largo, Antonio

2012-01-01

A computational study of the reactions of hydroxylamine and its ionized and protonated derivatives with acetic acid is provided. The reaction of neutral hydroxylamine with acetic acid, despite being clearly exothermic, involves a very large energy barrier. The reaction of ionized hydroxylamine with acetic acid is also clearly exothermic, but again a significant energy barrier is found (around 24 kcal mol –1 at the CCSD(T) level). The reaction of the most stable protonated isomer of hydroxylamine, NH 3 OH + , with acetic acid also involves a high barrier (more than 27 kcal mol –1 at the CCSD(T) level). Only the higher energy isomer, NH 2 OH + 2 , leads to a sensibly lower energy barrier (about 2.3 kcal mol –1 at the CCSD(T) level). Nevertheless, an estimate of the reaction coefficient at low temperatures such as those reigning in the interstellar medium gives very low values. Therefore, it seems that precursors of interstellar glycine could not be efficiently produced from the reactions of hydroxylamine-derived ions with acetic acid.

Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation

OpenAIRE

Baur, Markus A.

2003-01-01

Die Methode der enantioselektiven Decarboxylierung wurde angewendet, um Enantiomeren-angereicherte alpha-Aminosäurederivate und alpha-Fluorketone zu erhalten. Als Substrate wurden 2-N-Acetylamino-2-alkylmalonsäuremonoethylester beziehungsweise beta-Keto-benzylester verwendet. China-Alkaloide und Derivate davon wurden als Katalysatoren eingesetzt. Die besten erhaltenen Ergebnisse waren N-Acetyl-L-phenylalaninethylester mit 70% Enantiomerenüberschuß unter Verwendung der katalytisch aktiven Base...

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

Directory of Open Access Journals (Sweden)

M. Fernanda N. N. Carvalho

2016-04-01

Full Text Available A camphor-derived sulfonimine with a conjugated carbonyl group, oxoimine 1 (O2SNC10H13O, reacts with amino acids (glycine, L-alanine, L-phenylalanine, L-leucine to form a compound O2SNC10H13NC10H14NSO2 (2 which was characterized by spectroscopic means (MS and NMR and supported by DFT calculations. The product, a single diastereoisomer, contains two oxoimine units connected by a –N= bridge, and thus has a structural analogy to the colored product Ruhemann´s purple obtained by the ninhydrin reaction with amino acids. A plausible reaction mechanism that involves zwitterions, a Strecker degradation of an intermediate imine and water-catalyzed tautomerizations was developed by means of DFT calculations on potential transition states.

Obestatin Accelerates the Healing of Acetic Acid-Induced Colitis in Rats

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Aleksandra Matuszyk

2016-01-01

Full Text Available Obestatin, a 23-amino acid peptide derived from the proghrelin, has been shown to exhibit some protective and therapeutic effects in the gut. The aim of present study was to determine the effect of obestatin administration on the course of acetic acid-induced colitis in rats. Materials and Methods. Studies have been performed on male Wistar rats. Colitis was induced by a rectal enema with 3.5% acetic acid solution. Obestatin was administered intraperitoneally twice a day at a dose of 8 nmol/kg, starting 24 h after the induction of colitis. Seven or 14 days after the induction of colitis, the healing rate of the colon was evaluated. Results. Treatment with obestatin after induction of colitis accelerated the healing of colonic wall damage and this effect was associated with a decrease in the colitis-evoked increase in mucosal activity of myeloperoxidase and content of interleukin-1β. Moreover, obestatin administration significantly reversed the colitis-evoked decrease in mucosal blood flow and DNA synthesis. Conclusion. Administration of exogenous obestatin exhibits therapeutic effects in the course of acetic acid-induced colitis and this effect is related, at least in part, to the obestatin-evoked anti-inflammatory effect, an improvement of local blood flow, and an increase in cell proliferation in colonic mucosa.

The dominant detritus-feeding invertebrate in Arctic peat soils derives its essential amino acids from gut symbionts

DEFF Research Database (Denmark)

Larsen, Thomas; Ventura, Marc; Maraldo, Kristine

2016-01-01

insufficiencies of macronutrients such as essential amino acids (EAA). Documenting whether gut symbionts also function as partners for symbiotic EAA supplementation is important because the question of how some detritivores are able to subsist on nutritionally insufficient diets has remained unresolved. 3....... To answer this poorly understood nutritional aspect of symbiont-host interactions, we studied the enchytraeid worm, a bulk soil feeder that thrives in Arctic peatlands. In a combined field and laboratory study, we employed stable isotope fingerprinting of amino acids to identify the biosynthetic origins...... of amino acids to bacteria, fungi and plants in enchytraeids. 4. Enchytraeids collected from Arctic peatlands derived more than 80% of their EAA from bacteria. In a controlled feeding study with the enchytraeid Enchytraeus crypticus, EAA derived almost exclusively from gut bacteria when the worms fed...

Chemical Synthesis and Biological Activities of Novel Pleuromutilin Derivatives with Substituted Amino Moiety

Science.gov (United States)

Shang, Ruofeng; Wang, Shengyu; Xu, Ximing; Yi, Yunpeng; Guo, Wenzhu; YuLiu; Liang, Jianping

2013-01-01

Novel pleuromutilin derivatives designed based on the structure of valnemulin were synthesized and evaluated for their in vitro antibacterial activities. These pleuromutilin derivatives with substituted amino moiety exhibited excellent activities against methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Escherichia coli, and Streptococcus agalactiae. Compound 5b showed the highest antibacterial activities and even exceeded tiamulin. Moreover, the docking experiments provided information about the binding model between the synthesized compounds and peptidyl transferase center (PTC) of 23S rRNA. PMID:24376551

Chemical synthesis and biological activities of novel pleuromutilin derivatives with substituted amino moiety.

Directory of Open Access Journals (Sweden)

Ruofeng Shang

Full Text Available Novel pleuromutilin derivatives designed based on the structure of valnemulin were synthesized and evaluated for their in vitro antibacterial activities. These pleuromutilin derivatives with substituted amino moiety exhibited excellent activities against methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Escherichia coli, and Streptococcus agalactiae. Compound 5b showed the highest antibacterial activities and even exceeded tiamulin. Moreover, the docking experiments provided information about the binding model between the synthesized compounds and peptidyl transferase center (PTC of 23S rRNA.

Efficient Havinga–Kondepudi resolution of conglomerate amino acid derivatives by slow cooling and abrasive grinding

NARCIS (Netherlands)

Leeman, Michel; Noorduin, Wim L.; Millemaggi, Alessia; Vlieg, Elias; Meekes, Hugo; Enckevort, Willem J.P. van; Kaptein, Bernard; Kellogg, Richard M.

2010-01-01

The complete resolution of the conglomerate racemates of two amino acid derivatives susceptible to racemization in solution was achieved by slow crystallization from a supersaturated solution accompanied by cooling and abrasive grinding.

Azetidinic amino acids

DEFF Research Database (Denmark)

Bräuner-Osborne, Hans; Bunch, Lennart; Chopin, Nathalie

2005-01-01

A set of ten azetidinic amino acids, that can be envisioned as C-4 alkyl substituted analogues of trans-2-carboxyazetidine-3-acetic acid (t-CAA) and/or conformationally constrained analogues of (R)- or (S)-glutamic acid (Glu) have been synthesized in a diastereo- and enantiomerically pure form from...... of two diastereoisomers that were easily separated and converted in two steps into azetidinic amino acids. Azetidines 35-44 were characterized in binding studies on native ionotropic Glu receptors and in functional assays at cloned metabotropic receptors mGluR1, 2 and 4, representing group I, II and III...... beta-amino alcohols through a straightforward five step sequence. The key step of this synthesis is an original anionic 4-exo-tet ring closure that forms the azetidine ring upon an intramolecular Michael addition. This reaction was proven to be reversible and to lead to a thermodynamic distribution...

Functionalisation of mesoporous silica gel with 2-[(phosphonomethyl)-amino]acetic acid functional groups. Characterisation and application

Energy Technology Data Exchange (ETDEWEB)

Caldarola, Dario [Department of Applied Science and Technology, Politecnico di Torino, Corso Duca degli Abruzzi 24, 10129 Torino (Italy); Australian Centre for Research on Separation Sciences (ACROSS), University of Tasmania, Hobart, Tasmania 7001 (Australia); Mitev, Dimitar P. [Australian Centre for Research on Separation Sciences (ACROSS), University of Tasmania, Hobart, Tasmania 7001 (Australia); Marlin, Lucile [Ecole Nationale Superieure des Ingenieurs en Arts Chimiques et Technologiquesm, Toulouse (France); Irish Separation Science Cluster, Dublin City University, Dublin (Ireland); Nesterenko, Ekaterina P. [Irish Separation Science Cluster, Dublin City University, Dublin (Ireland); Paull, Brett [Australian Centre for Research on Separation Sciences (ACROSS), University of Tasmania, Hobart, Tasmania 7001 (Australia); Onida, Barbara [Department of Applied Science and Technology, Politecnico di Torino, Corso Duca degli Abruzzi 24, 10129 Torino (Italy); CR-INSTM for Materials with Controlled Porosity (Italy); Bruzzoniti, Maria Concetta; Carlo, Rosa Maria De; Sarzanini, Corrado [Analytical Chemistry Department, University of Torino, Via P. Giuria 5, 10125 Torino (Italy); Nesterenko, Pavel N., E-mail: Pavel.Nesterenko@utas.edu.au [Australian Centre for Research on Separation Sciences (ACROSS), University of Tasmania, Hobart, Tasmania 7001 (Australia)

2014-01-01

A new complexing adsorbent was prepared by chemical modification of mesoporous silica Kieselgel 60 (d{sub p} = 37–63 μm, average pore size 6 nm, specific surface area 425 m{sup 2} g{sup −1}) with 3-glycidoxypropyltrimethoxysilane and 2-[(phosphonomethyl)amino]acetic acid (PMA), commonly known as glyphosate. The prepared adsorbent was fully characterised using elemental analysis, thermal gravimetric analysis (TGA), acid–base potentiometric titration, Fourier Transform Infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), nitrogen adsorption isotherms at 77 K (BET), scanning electron microscopy with energy dispersive X-ray spectroscopy (SEM-EDS). The concentration of bonded PMA groups calculated from the nitrogen content was 0.38 mmol per gram. The adsorption of transition metal ions on PMA functionalised silica (HEPMAS) was studied from aqueous solutions having different pH and the following selectivity was established, Zn(II) < Co(II) < Cd(II) < Mn(II) < Ni(II) < Cu(II). The calculated values of distribution coefficients D for the adsorption of ecotoxic metal ions on HEPMAS are 5.0 × 10{sup 4}, 4.9 × 10{sup 5} and 2.6 × 10{sup 4} for Zn(II), Pb(II) and Cd(II), respectively.

Functionalisation of mesoporous silica gel with 2-[(phosphonomethyl)-amino]acetic acid functional groups. Characterisation and application

Science.gov (United States)

Caldarola, Dario; Mitev, Dimitar P.; Marlin, Lucile; Nesterenko, Ekaterina P.; Paull, Brett; Onida, Barbara; Bruzzoniti, Maria Concetta; Carlo, Rosa Maria De; Sarzanini, Corrado; Nesterenko, Pavel N.

2014-01-01

A new complexing adsorbent was prepared by chemical modification of mesoporous silica Kieselgel 60 (dp = 37-63 μm, average pore size 6 nm, specific surface area 425 m2 g-1) with 3-glycidoxypropyltrimethoxysilane and 2-[(phosphonomethyl)amino]acetic acid (PMA), commonly known as glyphosate. The prepared adsorbent was fully characterised using elemental analysis, thermal gravimetric analysis (TGA), acid-base potentiometric titration, Fourier Transform Infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), nitrogen adsorption isotherms at 77 K (BET), scanning electron microscopy with energy dispersive X-ray spectroscopy (SEM-EDS). The concentration of bonded PMA groups calculated from the nitrogen content was 0.38 mmol per gram. The adsorption of transition metal ions on PMA functionalised silica (HEPMAS) was studied from aqueous solutions having different pH and the following selectivity was established, Zn(II) < Co(II) < Cd(II) < Mn(II) < Ni(II) < Cu(II). The calculated values of distribution coefficients D for the adsorption of ecotoxic metal ions on HEPMAS are 5.0 × 104, 4.9 × 105 and 2.6 × 104 for Zn(II), Pb(II) and Cd(II), respectively.

Synthesis of some glycoside analogs and related compounds from 9-amino-6-(methylthio)-9H-purine.

Science.gov (United States)

Temple, C; Kussner, C L; Montgomery, J A

1975-12-01

Additional information on the anticancer activity of 9-amino-9H-purine-6(1H)-thione and its derivatives was sought by the synthesis of some 9-(substituted amino)-6-(methylthio)-9H-purines in which the 9-substituent contained functional groups capable of either reversible or irreversible binding with an enzymatic site. Condensation of 9-amino-6-(methylthio)-9H-purine (1) with some carbonyl compounds followed by hydride reduction of the azomethine linkage in the intermediates leads to the 2-pyrrolylmethyl (8), 2,3,4-trihydroxybutyl (10), and the 1,5-dihydroxy-2- and 3-pentyl (11 and 12) compounds. A 4-hydroxybutyl derivative (13) was obtained by alkylation of 18, the 9-acetyl derivative of 1, with 4-chlorobutyl acetate followed by saponification. The cyclization of 13 and 11 with a sulfonyl chloride gave the 9-pyrrolidin-1-yl (27) and the 9-[2-(tosyloxymethyl)pyrrolidin-1-yl] (28), respectively. Acylation of 1 with ethyl L-2-pyrrolidine-5-carboxylate and ethyl 1-methyl-5-pyrrolidone-3-carboxylate, respectively, in Me2SO containing NaH gave the corresponding amides 15 and 17. Alkylation of 18 with 1-bromo-2-chloroethane and epichlorohydrin gave the N-(2-chloroethyl) and N-(1,2-epoxy-3-propyl) derivatives 19 and 20. The chloro group of the chlorobutyl derivative of 18 was displaced with KSCN and NaN3, respectively, to give the thiocyanate and azido derivatives 23 and 24. Hydrogenation of the latter gave the amine (25), which was acylated with ethyl chloroformate to give the (ethoxycarbonyl)amino compound 26. None of these compounds showed activity against L1210 leukemia cells implanted ip in mice on a single-dose schedule, suggesting that the activity observed in the simpler 9-aminopurines resulted from cleavage of the hydrazino linkage to give pH-purine-6(1H)-thione.

Correlating enzymatic browning inhibition and antioxidant ability of Maillard reaction products derived from different amino acids.

Science.gov (United States)

Xu, Haining; Zhang, Xiaoming; Karangwa, Eric; Xia, Shuqin

2017-09-01

Up to now, only limited research on enzymatic browning inhibition capacity (BIC) of Maillard reaction products (MRPs) has been reported and there are still no overall and systematic researches on MRPs derived from different amino acids. In the present study, BIC and antioxidant capacity, including 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity and Fe 2+ reducing power activity, of the MRPs derived from 12 different amino acids and three reducing sugars were investigated. The MRPs of cysteine (Cys), cystine, arginine (Arg) and histidine (His) showed higher BIC compared to other amino acids. Lysine (Lys)-MRPs showed the highest absorbance value at 420 nm (A 420 ) but very limited BIC, whereas Cys-MRPs, showed the highest BIC and the lowest A 420 . The A 420 can roughly reflect the trend of BIC of MRPs from different amino acids, except Cys and Lys. MRPs from tyrosine (Tyr) showed the most potent antioxidant capacity but very limited BIC, whereas Cys-MRPs showed both higher antioxidant capacity and BIC compared to other amino acids. Partial least squares regression analysis showed positive and significant correlation between BIC and Fe 2+ reducing power of MRPs from 12 amino acids with glucose or fructose, except Lys, Cys and Tyr. The suitable pH for generating efficient browning inhibition compounds varies depending on different amino acids: acidic pH was favorable for Cys, whereas neutral and alkaline pH were suitable for His and Arg, respectively. Increasing both heating temperature and time over a certain range could improve the BIC of MRPs of Cys, His and Arg, whereas any further increase deteriorates their browning inhibition efficiencies. The types of amino acid, initial pH, temperature and time of the Maillard reaction were found to greatly influence the BIC and antioxidant capacity of the resulting MRPs. There is no clear relationship between BIC and the antioxidant capacity of MRPs when reactant type and processing parameters of the Maillard

Selective recovery of a pyridine derivative from an aqueous waste stream containing acetic acid and succinonitrile with solvent impregnated resins

NARCIS (Netherlands)

Bokhove, J.; Visser, T.J.; Schuur, Boelo; de Haan, A.B.

2015-01-01

Solvent impregnated resins (SIRs) were evaluated for the recovery of pyridine derivatives from an aqueous waste-stream containing also acetic acid and succinonitrile. For this purpose, a new solvent was developed, synthesized and impregnated in Amberlite XAD4. Sorption studies were used to determine

Palladium(II)-catalyzed ortho-C-H arylation/alkylation of N-benzoyl α-amino ester derivatives.

Science.gov (United States)

Misal Castro, Luis C; Chatani, Naoto

2014-04-14

The palladium-catalyzed arylation/alkylation of ortho-C-H bonds in N-benzoyl α-amino ester derivatives is described. In such a system both the NH-amido and the CO2R groups in the α-amino ester moieties play a role in successful C-H activation/C-C bond formation using iodoaryl coupling partners. A wide variety of functional groups and electron-rich/deficient iodoarenes are tolerated. The yields obtained range from 20 to 95%. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Root-uptake of 14C derived from acetic acid and 14C transfer to rice edible parts

International Nuclear Information System (INIS)

Ogiyama, Shinichi; Suzuki, Hiroyuki; Inubushi, Kazuyuki; Takeda, Hiroshi; Uchida, Shigeo

2010-01-01

Three types of culture experiments using paddy rice (Oryza sativa L.) were performed to examine root-uptake of 14 C in the form of acetic acid: double pot experiment (hydroponics), wet culture experiment (submerged sand medium), and chamber experiment (hydroponics and submerged sand medium). The 14 C radioactivity in the plant, mediums, and atmospheric carbon dioxide ( 14 CO 2 ) in the chamber were determined, and the distribution of 14 C in the plant was visualized using autoradiography. In the double pot experiment, the shoot of the plant and the lower root which was soaked in the culture solution had 14 C radioactivity, but the upper root which did not have contact with the solution had none. There were also 14 C radioactivity in the grains and roots in the wet culture experiment. Results of the chamber experiment showed that 14 CO 2 gas was released from the culture solution in both types of cultures. Results indicated that the 14 C-acetic acid absorbed by rice plant through its root would be very small. Most of the 14 C-acetic acid was transformed into gaseous forms either in the culture solution or rhizosphere. A relatively longer time would be needed to assimilate 14 C derived from acetic acid to grain parts after it was once absorbed by the shoot through the root. Availability of 14 C for the plant in sand culture was considered to be decreased compared with that for the plant in the hydroponics experiment. It was suggested that rice plant absorbed and assimilated 14 C through the plant roots not because of uptake of 14 C-acetic acid but because of uptake of 14 C in gaseous forms such as 14 CO 2 .

Synthesis of the derivatives of 6-amino-uracil labelled with C-14

Czech Academy of Sciences Publication Activity Database

Elbert, Tomáš; Hezký, Petr; Jansa, Petr

2016-01-01

Roč. 59, č. 14 (2016), s. 615-618 ISSN 0362-4803. [International Isotope Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds /12./. Princeton, 07.06.2015-11.06.2015] R&D Projects: GA MŠk LG13002 Institutional support: RVO:61388963 Keywords : 6-amino-uracil derivatives * specific activity assay using NMR * [C-14]cyanoacetic acid Subject RIV: CC - Organic Chemistry Impact factor: 1.745, year: 2016

A Standard Structure for Bile Acids and Derivatives

Directory of Open Access Journals (Sweden)

Francisco Meijide

2018-02-01

Full Text Available The crystal structures of two ester compounds (a monomer in its methyl ester form, with an amino isophthalic group, and a dimer in which the two steroid units are linked by a urea bridge recrystallized from ethyl acetate/methanol derived from cholic acid are described. Average bond lengths and bond angles from the crystal structures of 26 monomers and four dimers (some of them in several solvents of bile acids and esters (and derivatives are used for proposing a standard steroid nucleus. The hydrogen bond network and conformation of the lateral chain are also discussed. This standard structure was used to compare with the structures of both progesterone and cholesterol.

Quantum mechanics and molecular dynamics simulations of complexation of alkaline-earth and lanthanide cations by poly-amino-carboxylate ligands

International Nuclear Information System (INIS)

Durand, S.

1999-01-01

Molecular dynamics (MD) simulations on lanthanide(III) and alkaline-earth(II) complexes with poly-amino-carboxylates (ethylene-diamino-tetra-acetate EDTA 4- , ethylene-diamino-tri-acetate-acetic acid EDTA(H) 3- , tetra-aza-cyclo-dodecane-tetra-acetate DOTA 4- , methylene-imidine-acetate MIDA 2- ) are reported. First, a consistent set of Lennard-Jones parameters for La 3+ , Eu 3+ and Lu 3+ cations has been derived from free energy calculations in aqueous solution. Observed differences in hydration free energies, coordination distances and hydration numbers are reproduced. Then, the solution structures of 1:1 complexes of alkaline-earth and/or lanthanide cations with EDTA 4- , EDTA(H) 3- , DOTA 4- and 1:2 complexes of lanthanide cations with MIDA 2- were studied by MD in water. In addition, free energy calculations were performed to study, for each ligand, the relative thermodynamic stabilities of complexes with Ca 2+ vs Sr 2+ and vs Ba 2+ on the one hand, and with La 3+ vs Eu 3+ and vs Lu 3+ on the other hand. Model does not take into account explicitly polarization and charge transfer. However, the results qualitatively agree with experimental complexation data (structure and selectivities). (author)

A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid

DEFF Research Database (Denmark)

Bräuner-Osborne, Hans; Sløk, F A; Skjaerbaek, N

1996-01-01

The homologous series of acidic amino acids, ranging from aspartic acid (1) to 2-aminosuberic acid (5), and the corresponding series of 3-isoxazolol bioisosteres of these amino acids, ranging from (RS)-2-amino-2-(3-hydroxy-5-methylisoxazol-4-yl)acetic acid (AMAA, 6) to (RS)-2-amino-6-(3-hydroxy-5......-methylisoxazol-4-yl)hexanoic acid (10), were tested as ligands for metabotropic excitatory amino acid receptors (mGlu1 alpha, mGlu2, mGlu4a, and mGlu6). Whereas AMAA (6) and (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propinoic acid (AMPA, 7) are potent and highly selective agonists at N......-methyl-D-aspartic acid (NMDA) and AMPA receptors, respectively, the higher homologue of AMPA (7), (RS)-2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid (homo-AMPA, 8), is inactive at ionotropic excitatory amino acid receptors. Homo-AMPA (8), which is a 3-isoxazolol bioisostere of 2-aminoadipic acid (3), was...

Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids.

Science.gov (United States)

Cantú-Reyes, Margarita; Alvarado-Beltrán, Isabel; Ballinas-Indilí, Ricardo; Álvarez-Toledano, Cecilio; Hernández-Rodríguez, Marcos

2017-09-20

We report a one-pot synthesis of chiral β 2,2,3 -amino acids by the Mannich addition of bistrimethylsilyl ketene acetals to N-tert-butanesulfinyl imines followed by the removal of the chiral auxiliary. The synthesis and isolation of pure β-amino acid hydrochlorides were conducted under mild conditions, without strong bases and this method is operationally simple. The stereoselective reaction was promoted by two different activation methods that lead to different stereoisomers: (1) Lewis Acid (LA) catalysis with boron trifluoride diethyl etherate and (2) Lewis Base (LB) catalysis with tetrabutylammonium difluorotriphenylsilicate. The reaction presented good diastereoselectivity with LB activation and moderate to good dr with LA catalysis. The exceptions in both protocols were imines with electron donating groups in the aromatic ring.

Amino Acid Conjugated Anthraquinones from the Marine-Derived Fungus Penicillium sp. SCSIO sof101.

Science.gov (United States)

Luo, Minghe; Cui, Zhaomeng; Huang, Hongbo; Song, Xianqin; Sun, Aijun; Dang, Yongjun; Lu, Laichun; Ju, Jianhua

2017-05-26

Emodacidamides A-H (1-8), natural products featuring anthraquinone-amino acid conjugates, have been isolated from a marine-derived fungus, Penicillium sp. SCSIO sof101, together with known anthraquinones 9 and 10. The planar structures of 1-8 were elucidated using a combination of NMR spectroscopy and mass spectrometry. The absolute configurations of the amino acid residues were confirmed using Marfey's method and chiral-phase HPLC analyses. Additionally, isolates were evaluated for possible immunomodulatory and cytotoxic activities. Emodacidamides A (1), C (3), D (4), and E (5) inhibited interleukin-2 secretion from Jurkat cells with IC 50 values of 4.1, 5.1, 12, and 5.4 μM, respectively.

Synthesis of nanodiamond derivatives carrying amino functions and quantification by a modified Kaiser test

Directory of Open Access Journals (Sweden)

Gerald Jarre

2014-11-01

Full Text Available Nanodiamonds functionalized with different organic moieties carrying terminal amino groups have been synthesized. These include conjugates generated by Diels–Alder reactions of ortho-quinodimethanes formed in situ from pyrazine and 5,6-dihydrocyclobuta[d]pyrimidine derivatives. For the quantification of primary amino groups a modified photometric assay based on the Kaiser test has been developed and validated for different types of aminated nanodiamond. The results correspond well to values obtained by thermogravimetry. The method represents an alternative wet-chemical quantification method in cases where other techniques like elemental analysis fail due to unfavourable combustion behaviour of the analyte or other impediments.

Synthesis and antitumour activity of arctigenin amino acid ester derivatives against H22 hepatocellular carcinoma.

Science.gov (United States)

Cai, Enbo; Guo, Shijie; Yang, Limin; Han, Mei; Xia, Jing; Zhao, Yan; Gao, Xiaorui; Wang, Yu

2018-02-01

Arctigenin (ARG) is famous in its abundant pharmacological activity. However, many researches in it entered the bottleneck period because of its poor water solubility. The derivatives of ARG have been synthesised with five amino acids which have t-Butyloxy carbonyl (BOC) as a protective group. We examined the effects of removing BOC. The results showed that the amino acid derivatives without protective group have better water solubility and nitrite-clearing ability than ARG. Based on these results, ARG6' and ARG9' were selected at a dosage of 40 mg/kg to evaluate their antitumour activity. The percentage inhibition rate of ARG6' and ARG9' were 55.87 and 51.40, respectively, which was twice as much as ARG. Furthermore, they could increase liver and kidney indexes and produce less damage in these organs. In brief, this study provides a basis for new drug development.

Amino acid linked bromobenzoyl thiourea derivatives: syntheses, characterization and antimicrobial activities

International Nuclear Information System (INIS)

Raheel, A.; Din, I.U.; Badshah, A.; Rauf, M.K.; Andleeb, S.

2016-01-01

Five new bromobenzoyl thiourea derivatives (1-5) linked with different amino acids were synthesized via the reaction of bromobenzoyl chloride with potassium thiocyanide and the corresponding amines. The synthetic compounds were characterized by single crystal XRD, IR and NMR (/sup 1/H- and /sup 13/C-) spectroscopy in addition to elemental analysis and melting point determinations. These compounds were also preliminary analyzed for antifungal and antibacterial activity against different strains of fungi and bacteria, respectively. The data suggest that the compounds exhibited promising antimicrobial activity and may prove potential lead compounds as antimicrobial agent. (author)

Synthesis of novel 68Ga-labeled amino acid derivatives for positron emission tomography of cancer cells

International Nuclear Information System (INIS)

Shetty, Dinesh; Jeong, Jae Min; Ju, Chang Hwan; Lee, Yun-Sang; Jeong, Seo Young; Choi, Jae Yeon; Yang, Bo Yeun

2010-01-01

Objectives: We developed amino acid derivatives of 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid (DO2A) and 1,4,7,10-tetraazacyclododecane-1,4,7,-triacetic acid (DO3A) that can be labeled with 68 Ga, and we investigated their basic biological properties. Materials and methods: Alanine derivatives of DO2A and DO3A were synthesized by regiospecific nucleophilic attack of DO2tBu and DO3tBu on the β-position of Boc-L-serine-β-lactone, followed by acid hydrolysis. Also, homoalanine derivatives were synthesized by reacting with the protected bromo derivative of homoalanine, which was synthesized from N-Cbz-L-homoserine lactone. Further catalytic reduction and acid cleavage of protected groups resulted in the required products. All derivatives were labeled with 68 Ga. Cell uptake assays were carried out in Hep3B (human hepatoma) and U87MG (human glioma) cell lines at 37 o C. Positron emission tomography (PET) imaging studies were performed using balb/c mice xenografted with CT-26 (mouse colon cancer). Results: All compounds were labeled with >97% efficiency. According to in vitro studies, the labeled amino acid derivatives showed significantly greater uptakes than the control ( 68 Ga 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) in cancer cells. Small animal PET images for labeled compounds showed high tumor uptake, as well as kidney and bladder uptakes, at 30 min postinjection. 68 Ga-DO3A-homoalanine showed the highest standardized uptake value ratio (3.9±0.3), followed by 68 Ga-DO2A-alanine (3.1±0.2), 68 Ga-DO3A-alanine (2.8±0.2) and 68 Ga-DO2A-homoalanine (2.3±0.2). Conclusion: These derivatives were found to have high labeling efficiencies, high stabilities, high tumor cell uptakes, high tumor/nontumor xenograft uptakes and low nonspecific uptake in normal organs, except for the kidneys. However, the uptake mechanism of these derivatives remains unclear, and uptake via specific amino acid transporters needs to be demonstrated.

Hydrolysis of Acetic Anhydride in a CSTR

Directory of Open Access Journals (Sweden)

Veronica N. Coraci

2016-05-01

Full Text Available To find the optimal reactor volume and temperature for the hydrolysis of acetic anhydride at the lowest possible cost with a 90% conversion of acetic anhydride, a formula for the total cost of the reaction was created. Then, the first derivative was taken to find a value for the temperature. This value was then inputted into the second derivative of the equation to find the sign of the value which would indicate whether that point was a minima or maxima value. The minima value would then be the lowest total cost for the optimum reaction to take place.

Synthesis of Some Novel Heterocyclic and Schiff Base Derivatives as Antimicrobial Agents

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Mohamed E. Azab

2015-10-01

Full Text Available Treatment of 2,3-diaryloxirane-2,3-dicarbonitriles 1a–c with different nitrogen nucleophiles, e.g., hydrazine, methyl hydrazine, phenyl hydrazine, hydroxylamine, thiosemicarbazide, and/or 2-amino-5-phenyl-1,3,4-thiadiazole, afforded pyrazole, isoxazole, pyrrolotriazine, imidazolothiadiazole derivatives 2–5, respectively. Reacting pyrazoles 2a–c with aromatic aldehydes and/or methyl glycinate produced Schiff’s bases 7a–d and pyrazolo[3,4-b]-pyrazinone derivative 8, respectively. Treating 7 with ammonium acetate and/or hydrazine hydrate, furnished the imidazolopyrazole and pyrazolotriazine derivatives 9 and 10, respectively. Reaction of 8 with chloroacetic acid and/or diethyl malonate gave tricyclic compound 11 and triketone 12, respectively. On the other hand, compound 1 was reacted with active methylene precursors, e.g., acetylacetone and/or cyclopentanone producing adducts 14a,b which upon fusion with ammonium acetate furnished the 3-pyridone derivatives 15a,b, respectively. Some of newly synthesized compounds were screened for activity against bacterial and fungal strains and most of the newly synthesized compounds showed high antimicrobial activities. The structures of the new compounds were elucidated using IR, 1H-NMR, 13C-NMR and mass spectroscopy.

Reducing Renal Uptake of {sup 177}Lu Labeled CCK Derivative using Basic Amino Acids

Energy Technology Data Exchange (ETDEWEB)

Lee, Soyoung; Lim, Jaecheong; Joh, Eunha [Korea Atomic Energy Research Institute, Daejeon (Korea, Republic of)

2014-05-15

Radiolabeled peptides have been designed to target the relative receptors overespressed in tumor cells, such as integrin αvβ3, gastrin-releasing peptide receptor (GRPR), melanocortin-1 receptor (MC1-R), glucagon-like peptide-a receptor (GLP-1R), and cholecystokinin (CCK) receptor. Most of these peptides are eliminated from the body via the kidney and are partly reabsorbed in the proximal tubular cells. However, the high renal uptake of the radiolabeled peptides may lead to renal toxicity. In this study we investigated various amino acid solutions to reduce the renal uptake of {sup 177}Lu-DOTA-CCK derivative. Renal uptake of {sup 177}Lu-DOTA-CCK derivative is effectively reduced by the administration of positively charged amino acids. The administration of 12 mg of L-lysine was as effective in reducing the renal uptake as 6 mg of lysine and 6 mg of arginine combinations. Further studies will be performed to identify the most potent inhibitor of renal reuptake of radiolabeled peptides and minimize the chance of unwanted side effects.

Acetalization of furfural with zeolites under benign reaction conditions

DEFF Research Database (Denmark)

Rubio-Caballeroa, Juan Miguel; Shunmugavel, Saravanamurugan; Maireles-Torres, Pedro

2014-01-01

Acetalization is a viable method to protect carbonyl functionalities in organic compounds and offers apotential synthetic strategy for synthesizing derived chemicals. In this work, several families of commer-cial zeolites have been employed as solid acid catalysts in the acetalization of furfural...

Separation of polyethylene glycols and amino-terminated polyethylene glycols by high-performance liquid chromatography under near critical conditions.

Science.gov (United States)

Wei, Y-Z; Zhuo, R-X; Jiang, X-L

2016-05-20

The separation and characterization of polyethylene glycols (PEGs) and amino-substituted derivatives on common silica-based reversed-phase packing columns using isocratic elution is described. This separation is achieved by liquid chromatography under the near critical conditions (LCCC), based on the number of amino functional end groups without obvious effect of molar mass for PEGs. The mobile phase is acetonitrile in water with an optimal ammonium acetate buffer. The separation mechanism of PEG and amino-substituted PEG under the near LCCC on silica-based packing columns is confirmed to be ion-exchange interaction. Under the LCCC of PEG backbone, with fine tune of buffer concentration, the retention factor ratios for benzylamine and phenol in buffered mobile phases, α(benzylamine/phenol)-values, were used to assess the ion-exchange capacity on silica-based reversed-phase packing columns. To the best of our knowledge, this is the first report on separation of amino-functional PEGs independent of the molar mass by isocratic elution using common C18 or phenyl reversed-phase packing columns. Copyright © 2016 Elsevier B.V. All rights reserved.

40 CFR 721.10055 - 1-Propanaminium, 3-amino-N-(carboxymethyl)-N,N-dimethyl-, N-soya acyl derivs., inner salts.

Science.gov (United States)

2010-07-01

...-(carboxymethyl)-N,N-dimethyl-, N-soya acyl derivs., inner salts. 721.10055 Section 721.10055 Protection of...-amino-N-(carboxymethyl)-N,N-dimethyl-, N-soya acyl derivs., inner salts. (a) Chemical substance and...-(carboxymethyl)-N,N-dimethyl-, N-soya acyl derivs., inner salts (PMN P-03-46; CAS No. 136504-87-5) is subject to...

(+)-camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc

NARCIS (Netherlands)

Vries, André H.M. de; Imbos, Rosalinde; Feringa, Bernard

1997-01-01

Several novel tri- and tetradentate amino alcohol ligands, all derived from (+)-camphor, have been synthesized by using specific N-alkylation procedures. The amino alcohols were employed as chiral ligands in the nickel catalyzed conjugate additions of diethylzine to chalcone and cyclohexenone as

Comparative photocatalytic study of two selected pesticide derivatives, indole-3-acetic acid and indole-3-butyric acid in aqueous suspensions of titanium dioxide

Energy Technology Data Exchange (ETDEWEB)

Qamar, M. [Department of Chemistry, Aligarh Muslim University, Aligarh 202002 (India); Muneer, M. [Department of Chemistry, Aligarh Muslim University, Aligarh 202002 (India)]. E-mail: cht12mm@amu.ac.in

2005-04-11

Heterogeneous photocatalysed degradation of two selected pesticide derivatives such as indole-3-acetic acid (IAA) and indole-3-butyric acid (IBA) has been investigated in aqueous suspensions of titanium dioxide by monitoring the change in substrate concentration employing UV spectroscopic analysis technique and depletion in total organic carbon (TOC) content as a function of irradiation time. The degradation kinetics was studied under different conditions such as pH, types of TiO{sub 2,} substrate and catalyst concentration, and in the presence of electron acceptor such as hydrogen peroxide (H{sub 2}O{sub 2}) besides molecular oxygen. The degradation rates were found to be strongly influenced by all the above parameters. The photocatalyst Degussa P25 showed comparatively highest photocatalytics. The pesticide derivative, indole-3-acetic acid was found to degrade slightly faster than indole-3-butyric acid.

Determination of amino acids in grape-derived products: a review.

Science.gov (United States)

Callejón, R M; Troncoso, A M; Morales, M L

2010-06-15

The amino acids present in foods and beverages affect the quality of these products and they play an important role in enology. Amino acids are consumed by yeasts as a source of nitrogen during alcoholic fermentation and are precursors of aroma compounds. In this review various chromatographic methodologies for the determination of amino acids are described, and specific applications for the analysis of amino acid content are discussed. Amino acids usually need to be derivatized to make them more detectable. Several derivatizing reagents have been employed for the determination of amino acids in enological applications, and each has its advantages and disadvantages.

Ulipristal acetate versus leuprolide acetate for uterine fibroids.

Science.gov (United States)

Donnez, Jacques; Tomaszewski, Janusz; Vázquez, Francisco; Bouchard, Philippe; Lemieszczuk, Boguslav; Baró, Francesco; Nouri, Kazem; Selvaggi, Luigi; Sodowski, Krzysztof; Bestel, Elke; Terrill, Paul; Osterloh, Ian; Loumaye, Ernest

2012-02-02

The efficacy and side-effect profile of ulipristal acetate as compared with those of leuprolide acetate for the treatment of symptomatic uterine fibroids before surgery are unclear. In this double-blind noninferiority trial, we randomly assigned 307 patients with symptomatic fibroids and excessive uterine bleeding to receive 3 months of daily therapy with oral ulipristal acetate (at a dose of either 5 mg or 10 mg) or once-monthly intramuscular injections of leuprolide acetate (at a dose of 3.75 mg). The primary outcome was the proportion of patients with controlled bleeding at week 13, with a prespecified noninferiority margin of -20%. Uterine bleeding was controlled in 90% of patients receiving 5 mg of ulipristal acetate, in 98% of those receiving 10 mg of ulipristal acetate, and in 89% of those receiving leuprolide acetate, for differences (as compared with leuprolide acetate) of 1.2 percentage points (95% confidence interval [CI], -9.3 to 11.8) for 5 mg of ulipristal acetate and 8.8 percentage points (95% CI, 0.4 to 18.3) for 10 mg of ulipristal acetate. Median times to amenorrhea were 7 days for patients receiving 5 mg of ulipristal acetate, 5 days for those receiving 10 mg of ulipristal acetate, and 21 days for those receiving leuprolide acetate. Moderate-to-severe hot flashes were reported for 11% of patients receiving 5 mg of ulipristal acetate, for 10% of those receiving 10 mg of ulipristal acetate, and for 40% of those receiving leuprolide acetate (P<0.001 for each dose of ulipristal acetate vs. leuprolide acetate). Both the 5-mg and 10-mg daily doses of ulipristal acetate were noninferior to once-monthly leuprolide acetate in controlling uterine bleeding and were significantly less likely to cause hot flashes. (Funded by PregLem; ClinicalTrials.gov number, NCT00740831.).

Synthesis of novel {sup 68}Ga-labeled amino acid derivatives for positron emission tomography of cancer cells

Energy Technology Data Exchange (ETDEWEB)

Shetty, Dinesh [Department of Nuclear Medicine, Institute of Radiation Medicine, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Cancer Research Institute, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Department of Radiation Applied Life Science, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Jeong, Jae Min, E-mail: jmjng@snu.ac.k [Department of Nuclear Medicine, Institute of Radiation Medicine, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Cancer Research Institute, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Department of Radiation Applied Life Science, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Ju, Chang Hwan [Cancer Research Institute, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul (Korea, Republic of); Lee, Yun-Sang [Department of Nuclear Medicine, Institute of Radiation Medicine, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Department of Radiation Applied Life Science, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Jeong, Seo Young [Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul (Korea, Republic of); Choi, Jae Yeon; Yang, Bo Yeun [Department of Nuclear Medicine, Institute of Radiation Medicine, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Cancer Research Institute, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of); Department of Radiation Applied Life Science, Seoul National University College of Medicine, Seoul 110-744 (Korea, Republic of)

2010-11-15

Objectives: We developed amino acid derivatives of 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid (DO2A) and 1,4,7,10-tetraazacyclododecane-1,4,7,-triacetic acid (DO3A) that can be labeled with {sup 68}Ga, and we investigated their basic biological properties. Materials and methods: Alanine derivatives of DO2A and DO3A were synthesized by regiospecific nucleophilic attack of DO2tBu and DO3tBu on the {beta}-position of Boc-L-serine-{beta}-lactone, followed by acid hydrolysis. Also, homoalanine derivatives were synthesized by reacting with the protected bromo derivative of homoalanine, which was synthesized from N-Cbz-L-homoserine lactone. Further catalytic reduction and acid cleavage of protected groups resulted in the required products. All derivatives were labeled with {sup 68}Ga. Cell uptake assays were carried out in Hep3B (human hepatoma) and U87MG (human glioma) cell lines at 37{sup o}C. Positron emission tomography (PET) imaging studies were performed using balb/c mice xenografted with CT-26 (mouse colon cancer). Results: All compounds were labeled with >97% efficiency. According to in vitro studies, the labeled amino acid derivatives showed significantly greater uptakes than the control ({sup 68}Ga 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) in cancer cells. Small animal PET images for labeled compounds showed high tumor uptake, as well as kidney and bladder uptakes, at 30 min postinjection. {sup 68}Ga-DO3A-homoalanine showed the highest standardized uptake value ratio (3.9{+-}0.3), followed by {sup 68}Ga-DO2A-alanine (3.1{+-}0.2), {sup 68}Ga-DO3A-alanine (2.8{+-}0.2) and {sup 68}Ga-DO2A-homoalanine (2.3{+-}0.2). Conclusion: These derivatives were found to have high labeling efficiencies, high stabilities, high tumor cell uptakes, high tumor/nontumor xenograft uptakes and low nonspecific uptake in normal organs, except for the kidneys. However, the uptake mechanism of these derivatives remains unclear, and uptake via specific amino acid

Novel 2-Thioxanthine and Dipyrimidopyridine Derivatives: Synthesis and Antimicrobial Activity

Directory of Open Access Journals (Sweden)

Samar El-kalyoubi

2015-10-01

Full Text Available Several fused imidazolopyrimidines were synthesized starting from 6-amino-1-methyl-2-thiouracil (1 followed by nitrosation, reduction and condensation with different aromatic aldehydes to give Schiff’s base. The dehydrocyclization of Schiff’s bases using iodine/DMF gave Compounds 5a–g. The methylation of 5a–g using a simple alkylating agent as dimethyl sulfate ((CH32SO4 gave either monoalkylated imidazolopyrimidine 6a–g at room temperature or dialkylated derivatives 7a–g on heating 6a–g with ((CH32SO4. On the other hand, treatment of 1 with different aromatic aldehydes in absolute ethanol in the presence of conc. hydrochloric acid at room temperature and/or reflux with acetic acid afforded bis-5,5́-diuracylmethylene 8a–e, which cyclized on heating with a mixture of acetic acid/HCl (1:1 to give 9a–e. Compounds 9a–e can be obtained directly by refluxing of Compound 1 with a mixture of acetic acid/HCl. The synthesized new compounds were screened for antimicrobial activity, and the MIC was measured.

Primary amino acid derivatives: substitution of the 4'-N'-benzylamide site in (R)-N'-benzyl 2-amino-3-methylbutanamide, (R)-N'-benzyl 2-amino-3,3-dimethylbutanamide, and (R)-N'-benzyl 2-amino-3-methoxypropionamide provides potent anticonvulsants with pain-attenuating properties.

Science.gov (United States)

King, Amber M; Salomé, Christophe; Salomé-Grosjean, Elise; De Ryck, Marc; Kaminski, Rafal; Valade, Anne; Stables, James P; Kohn, Harold

2011-10-13

Recently, we reported that select N'-benzyl 2-substituted 2-amino acetamides (primary amino acid derivatives (PAADs)) exhibited pronounced activities in established whole animal anticonvulsant (i.e., maximal electroshock seizure (MES)) and neuropathic pain (i.e., formalin) models. The anticonvulsant activities of C(2)-hydrocarbon N'-benzyl 2-amino acetamides (MES ED(50) = 13-21 mg/kg) exceeded those of phenobarbital (ED(50) = 22 mg/kg). Two additional studies defining the structure-activity relationship of PAADs are presented in this issue of the journal. In this study, we demonstrated that the anticonvulsant activities of (R)-N'-benzyl 2-amino-3-methylbutanamide and (R)-N'-benzyl 2-amino-3,3-dimethylbutanamide were sensitive to substituents at the 4'-N'-benzylamide site; electron-withdrawing groups retained activity, electron-donating groups led to a loss of activity, and incorporating either a 3-fluorobenzyloxy or 3-fluorophenoxymethyl group using a rationally designed multiple ligand approach improved activity. Additionally, we showed that substituents at the 4'-N'-benzylamide site of (R)-N'-benzyl 2-amino-3-methoxypropionamide also improved anticonvulsant activity, with the 3-fluorophenoxymethyl group providing the largest (∼4-fold) increase in activity (ED(50) = 8.9 mg/kg), a value that surpassed phenytoin (ED(50) = 9.5 mg/kg). Collectively, the pharmacological findings provided new information that C(2)-hydrocarbon PAADs represent a novel class of anticonvulsants.

Acute toxicity of 5-(furan-2-yl, 2-metylfuran-3-yl-4-amino-1,2,4-triazole-3-thiol alkyl derivatives

Directory of Open Access Journals (Sweden)

D. M. Danilchenko

2017-09-01

Full Text Available The purpose of our work was the further exploration of the new 5-(furan-2-yl, 2-metylfuran-3-yl-4-amino-1,2,4-triazole-3-thiol alkyl derivatives’ acute toxicity, setting some patterns of alkyl substituents influence by the Sulfur atom on the acute toxicity. Research materials and methods. In this study we used first time synthesized 5-(furan-2-yl, 2-metylfuran-3-yl-4-amino-4H-1,2,4-triazole-3-thione derivatives. Acute toxicity was conducted on white rats weighing 160–250 g, which were injected once intraperitoneally with the investigated substances. The rats were received from the nursery of the Pharmacology and Toxicology Institute of Ukraine Medical Sciences Academy. The animals were kept on a standard diet with natural light mode "day-night". Results and their discussion. After the acute toxicity studies in a group of 5-(furan-2-yl, 2-metylfuran-3-yl-4-amino-4H-1,2,4-triazole 3-alkyl derivatives it was found that among all studied structures the most toxic was 2e, LD50 of which was 263 mg/kg, and the least toxic compound was 2a, LD50 of which was 1570 mg/kg, that belongs to the V toxicity class. After comparing the acute toxicity of well-known antimycotic agent fluconazole with the studied compounds it can be argued that most compounds are less toxic than the comparison drug fluconazole with the index of LD50 ˃320 mg/kg. It was found that the transition in a group from butyl to decyl, octyl, ventyl, propyl, nonyl and heptyl substituents in the molecule of 3-alkylthio 5-(furan-2-yl-4-amino-4H-1,2,4-triazole is accompanied by the toxicity increasing. Speaking about the 5-(2-metylfuran-3-yl-4-amino-4H-1,2,4-triazole 3-alkylthio derivatives we can find that this dependence is observed in a number from propyl, pentyl, nonil, butyl, heksyl, octyl and heptyl hydrocarbon chains. Conclusions. The investigated 3-alkylthio 5-(furan-2-yl, 2-metylfuran-3-yl-4-amino-4H-1,2,4-triazole derivatives belong to the IV-V toxicity class. The toxicity of 5

Root-uptake of {sup 14}C derived from acetic acid and {sup 14}C transfer to rice edible parts

Energy Technology Data Exchange (ETDEWEB)

Ogiyama, Shinichi [Office of Biospheric Assessment for Waste Disposal, National Institute of Radiological Sciences, 4-9-1 Anagawa, Inage-ku, Chiba-shi 263-8555 (Japan)], E-mail: ogiyama@nirs.go.jp; Suzuki, Hiroyuki [Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-5522 (Japan); Inubushi, Kazuyuki [Graduate School of Horticulture, Chiba University, 648 Matsudo, Matsudo-shi 271-8510 (Japan); Takeda, Hiroshi; Uchida, Shigeo [Office of Biospheric Assessment for Waste Disposal, National Institute of Radiological Sciences, 4-9-1 Anagawa, Inage-ku, Chiba-shi 263-8555 (Japan)

2010-02-15

Three types of culture experiments using paddy rice (Oryza sativa L.) were performed to examine root-uptake of {sup 14}C in the form of acetic acid: double pot experiment (hydroponics), wet culture experiment (submerged sand medium), and chamber experiment (hydroponics and submerged sand medium). The {sup 14}C radioactivity in the plant, mediums, and atmospheric carbon dioxide ({sup 14}CO{sub 2}) in the chamber were determined, and the distribution of {sup 14}C in the plant was visualized using autoradiography. In the double pot experiment, the shoot of the plant and the lower root which was soaked in the culture solution had {sup 14}C radioactivity, but the upper root which did not have contact with the solution had none. There were also {sup 14}C radioactivity in the grains and roots in the wet culture experiment. Results of the chamber experiment showed that {sup 14}CO{sub 2} gas was released from the culture solution in both types of cultures. Results indicated that the {sup 14}C-acetic acid absorbed by rice plant through its root would be very small. Most of the {sup 14}C-acetic acid was transformed into gaseous forms either in the culture solution or rhizosphere. A relatively longer time would be needed to assimilate {sup 14}C derived from acetic acid to grain parts after it was once absorbed by the shoot through the root. Availability of {sup 14}C for the plant in sand culture was considered to be decreased compared with that for the plant in the hydroponics experiment. It was suggested that rice plant absorbed and assimilated {sup 14}C through the plant roots not because of uptake of {sup 14}C-acetic acid but because of uptake of {sup 14}C in gaseous forms such as {sup 14}CO{sub 2}.

Synthesis and antibacterial activities of 1-N [(S)-omega-amino-2-hydroxyalkyl] kanamycin A derivatives.

Science.gov (United States)

Richardson, K; Jevons, S; Moore, J W; Ross, B C; Wright, J R

1977-10-01

Four 1-N-aminohydroxy-alkyl derivatives of kanamycin A were prepared and their in vitro activities against aminoglycoside-sensitive and aminoglycoside-resistant organisms were compared with amikacin. 1-N-[(S)-4-Amino-2-hydroxybutyl] kanamycin A (Fig. 1, compound 2, code no. UK-18,892) was equipotent to amikacin in all these tests and in mouse protection studies.

Performance, kinetics, and equilibrium of methylene blue adsorption on biochar derived from eucalyptus saw dust modified with citric, tartaric, and acetic acids.

Science.gov (United States)

Sun, Lei; Chen, Dongmei; Wan, Shungang; Yu, Zebin

2015-12-01

Biochar derived from eucalyptus saw dust modified with citric, tartaric, and acetic acids at low temperatures was utilized as adsorbent to remove methylene blue (MB) from aqueous solutions. Fourier transform infrared spectroscopy analysis showed that the carboxyl group was introduced on the biochar surface. Adsorption experiment data indicated that eucalyptus saw dust modified with citric acid showed higher MB adsorption efficiency than that modified with tartaric and acetic acids. Pseudo-second-order kinetics was the most suitable model for describing MB adsorption on biochar compared with pseudo-first-order, Elovich, and intraparticle diffusion models. The calculated values of ΔG(0) and ΔH(0) indicated the spontaneous and endothermic nature of the adsorption process. MB adsorption on biochar followed the Langmuir isotherm. The maximum adsorption capacities for eucalyptus saw dust modified with citric, tartaric, and acetic acids were 178.57, 99.01, and 29.94 mg g(-1), respectively, at 35°C. Copyright © 2015 Elsevier Ltd. All rights reserved.

α-Amino Acid Derived Benzimidazole-Linked Rhodamines: A Case of Substitution Effect at the Amino Acid Site toward Spiro Ring Opening for Selective Sensing of Al3+ Ions.

Science.gov (United States)

Majumdar, Anupam; Mondal, Subhendu; Daniliuc, Constantin G; Sahu, Debashis; Ganguly, Bishwajit; Ghosh, Sourav; Ghosh, Utpal; Ghosh, Kumaresh

2017-08-07

α-Amino acid derived benzimidazole-linked rhodamines have been synthesized, and their metal ion sensing properties have been evaluated. Experimentally, l-valine- and l-phenylglycine-derived benzimidazole-based rhodamines 1 and 2 selectively recognize Al 3+ ion in aqueous CH 3 CN (CH 3 CN/H 2 O 4/1 v/v, 10 mM tris HCl buffer, pH 7.0) over the other cations by exhibiting color and "turn-on" emission changes. In contrast, glycine-derived benzimidazole 3 remains silent in the recognition event and emphasizes the role of α-substitution of amino acid undertaken in the design. The fact has been addressed on the basis of the single-crystal X-ray structures and theoretical calculations. Moreover, pink 1·Al 3+ and 2·Al 3+ ensembles selectively sensed F - ions over other halides through a discharge of color. Importantly, compounds 1 and 2 are cell permeable and have been used as imaging reagents for the detection of Al 3+ uptake in human lung carcinoma cell line A549.

Nutritional and medicinal aspects of D-amino acids.

Science.gov (United States)

Friedman, Mendel; Levin, Carol E

2012-05-01

This paper reviews and interprets a method for determining the nutritional value of D-amino acids, D-peptides, and amino acid derivatives using a growth assay in mice fed a synthetic all-amino acid diet. A large number of experiments were carried out in which a molar equivalent of the test compound replaced a nutritionally essential amino acid such as L-lysine (L-Lys), L-methionine (L-Met), L-phenylalanine (L-Phe), and L-tryptophan (L-Trp) as well as the semi-essential amino acids L-cysteine (L-Cys) and L-tyrosine (L-Tyr). The results show wide-ranging variations in the biological utilization of test substances. The method is generally applicable to the determination of the biological utilization and safety of any amino acid derivative as a potential nutritional source of the corresponding L-amino acid. Because the organism is forced to use the D-amino acid or amino acid derivative as the sole source of the essential or semi-essential amino acid being replaced, and because a free amino acid diet allows better control of composition, the use of all-amino-acid diets for such determinations may be preferable to protein-based diets. Also covered are brief summaries of the widely scattered literature on dietary and pharmacological aspects of 27 individual D-amino acids, D-peptides, and isomeric amino acid derivatives and suggested research needs in each of these areas. The described results provide a valuable record and resource for further progress on the multifaceted aspects of D-amino acids in food and biological samples.

First total synthesis of (-)-ichthyothereol and its acetate.

Science.gov (United States)

Mukai, C; Miyakoshi, N; Hanaoka, M

2001-08-24

The first and stereoselective total syntheses of (-)-ichthyothereol (1) and its acetate ((+)-2) were achieved by incorporation of the two chiral centers of diethyl L-tartrate. The starting diethyl L-tartrate was converted into trans-2-ethynyl-3-hydroxytetrahydropyran 14 in a stereoselective manner via the endo mode cyclization of the epoxy-alkyne derivative 12. The alcohol 12 was then transformed into (E)-iodoolefin derivative 15, which was exposed to a coupling reaction with 1-tributylstannyl-1,3,5-heptyne (19), derived from the corresponding 1-trimethylsilyl-1,3,5-heptyne (18), under Stille conditions to produce the all-carbon framework of the target natural products. Chemical modification of the coupled product 20 under conventional conditions completed the first total synthesis of (-)-ichthyothereol (1) and its acetate ((+)-2).

Hierarchical porous carbon derived from Allium cepa for supercapacitors through direct carbonization method with the assist of calcium acetate

KAUST Repository

Xu, Jinhui; Zhang, Wenli; Hou, Dianxun; Huang, Weimin; Lin, Haibo

2017-01-01

In this paper, a direction carbonization method was used to prepare porous carbon from Allium cepa for supercapacitor applications. In this method, calcium acetate was used to assist carbonization process. Scanning electron microscope (SEM) and N2 adsorption/desorption method were used to characterize the morphology, Brunauer-Emmett-Teller (BET) specific surface area and pore size distribution of porous carbon derived from Allium cepa (onion derived porous carbon, OPC). OPC is of hierarchical porous structure with high specific surface area and relatively high specific capacitance. OPC possesses relatively high specific surface area of 533.5 m2/g. What’s more, OPC possesses a specific capacitance of 133.5 F/g at scan rate of 5 mV/s.

Hierarchical porous carbon derived from Allium cepa for supercapacitors through direct carbonization method with the assist of calcium acetate

KAUST Repository

Xu, Jinhui

2017-11-02

In this paper, a direction carbonization method was used to prepare porous carbon from Allium cepa for supercapacitor applications. In this method, calcium acetate was used to assist carbonization process. Scanning electron microscope (SEM) and N2 adsorption/desorption method were used to characterize the morphology, Brunauer-Emmett-Teller (BET) specific surface area and pore size distribution of porous carbon derived from Allium cepa (onion derived porous carbon, OPC). OPC is of hierarchical porous structure with high specific surface area and relatively high specific capacitance. OPC possesses relatively high specific surface area of 533.5 m2/g. What’s more, OPC possesses a specific capacitance of 133.5 F/g at scan rate of 5 mV/s.

The effects of aromatic amino acid derivatives on the excitability of an identifiable giant neurone of the African giant snail (Achatina fulica Férussac).

Science.gov (United States)

Takeuchi, H.; Tamura, H.

1980-01-01

1 The effects of derivatives of aromatic amino acids on the excitability of an identifiable giant neurone (TAN, tonically autoactive neurone) of the African giant snail (Achatina fulica Férussac) were examined. 2 The following substances had marked inhibitory effects on TAN using bath application: N-beta-phenylpropionyl-L-Tyr and N-beta-phenylpropionyl-L-Trp (critical concentration, 3 x 10(-7) M), N-beta-phenylpropionyl-L-Phe, N-cinnamoyl-DL-Trp and N-phenoxyacetyl-L-Trp (critical concentration, 10(-5) to 3 x 10(-5) M). However, N-beta-phenylpropionyl-D-Tyr and N-beta-phenylpropionyl tyramine had no effect. 3 Microdrop (150 micrometers in diameter) application of N-beta-phenylpropionyl-L-Tyr or N-beta-phenylpropionyl-l-trp containing about 100 pg resulted in marked inhibitory effects on TAN. The effect was observed in Ca2+-free, Mg2+-rich (24 mM) solution. Substitution of Cl- by acetate did not alter the response. This indicates that the two substances act directly on the TAN membrane and not via synaptic influences, and that the inhibition produced by the two substances is not due to the permeability increase of the TAN membrane to Cl-. PMID:7378654

Bismuth nitrate as an efficient recyclable catalyst for the one-pot multi component synthesis of 1,4-dihydropyridine derivatives through unsymmetrical Hantzsch reaction

Directory of Open Access Journals (Sweden)

S. Sheik Mansoor

2016-09-01

Full Text Available Bismuth nitrate catalyzed efficient Hantzsch reaction via four-component coupling reactions of aromatic aldehydes, 5,5-dimethyl-1,3-cyclohexanedione (dimedone, ethyl acetoacetate and ammonium acetate at 80 °C temperature was described as the preparation of 1,4-dihydropyridine derivatives. 2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives are also prepared under the same experimental conditions using aldehydes, dimedone, malononitrile and ammonium acetate in good yield. The higher catalytic activity of Bi(NO3·5H2O is ascribed to its high acidity, thermal stability and water tolerance. The process presented here is operationally simple, environmentally benign and has excellent yield. Furthermore, the catalyst can be recovered conveniently and reused efficiently.

CcpA and CodY Coordinate Acetate Metabolism in Streptococcus mutans.

Science.gov (United States)

Kim, Jeong Nam; Burne, Robert A

2017-04-01

In the dental caries pathogen Streptococcus mutans , phosphotransacetylase (Pta) and acetate kinase (Ack) convert pyruvate into acetate with the concomitant generation of ATP. The genes for this pathway are tightly regulated by multiple environmental and intracellular inputs, but the basis for differential expression of the genes for Pta and Ack in S. mutans had not been investigated. Here, we show that inactivation in S. mutans of ccpA or codY reduced the activity of the ackA promoter, whereas a ccpA mutant displayed elevated pta promoter activity. The interactions of CcpA with the promoter regions of both genes were observed using electrophoretic mobility shift and DNase protection assays. CodY bound to the ackA promoter region but only in the presence of branched-chain amino acids (BCAAs). DNase footprinting revealed that the upstream region of both genes contains two catabolite-responsive elements ( cre1 and cre2 ) that can be bound by CcpA. Notably, the cre2 site of ackA overlaps with a CodY-binding site. The CcpA- and CodY-binding sites in the promoter region of both genes were further defined by site-directed mutagenesis. Some differences between the reported consensus CodY binding site and the region protected by S. mutans CodY were noted. Transcription of the pta and ackA genes in the ccpA mutant strain was markedly different at low pH relative to transcription at neutral pH. Thus, CcpA and CodY are direct regulators of transcription of ackA and pta in S. mutans that optimize acetate metabolism in response to carbohydrate, amino acid availability, and environmental pH. IMPORTANCE The human dental caries pathogen Streptococcus mutans is remarkably adept at coping with extended periods of carbohydrate limitation during fasting periods. The phosphotransacetylase-acetate kinase (Pta-Ack) pathway in S. mutans modulates carbohydrate flux and fine-tunes the ability of the organisms to cope with stressors that are commonly encountered in the oral cavity. Here, we

Isocyanides Derived from α,α-Disubstituted Amino Acids: Synthesis and Antifouling Activity Assessment.

Science.gov (United States)

Inoue, Yuki; Takashima, Shuhei; Nogata, Yasuyuki; Yoshimura, Erina; Chiba, Kazuhiro; Kitano, Yoshikazu

2018-03-01

Herein, we contribute to the development of environmentally friendly antifoulants by synthesizing eighteen isocyanides derived from α,α-disubstituted amino acids and evaluating their antifouling activity/toxicity against the cypris larvae of the Balanus amphitrite barnacle. Almost all isocyanides showed good antifouling activity without significant toxicity and exhibited EC 50 values of 0.07 - 7.30 μg/mL after 120-h exposure. The lowest EC 50 values were observed for valine-, methionine-, and phenylalanine-derived isocyanides, which achieved > 95% cypris larvae settlement inhibition at concentrations of less than 30 μg/mL without exhibiting significant toxicity. Thus, the prepared isocyanides should be useful for further research focused on the development of environmentally friendly antifouling agents. © 2018 Wiley-VHCA AG, Zurich, Switzerland.

Conjugation chemistry through acetals toward a dextran-based delivery system for controlled release of siRNA

KAUST Repository

Cui, Lina

2012-09-26

New conjugation chemistry for polysaccharides, exemplified by dextran, was developed to enable the attachment of therapeutic or other functional moieties to the polysaccharide through cleavable acetal linkages. The acid-lability of the acetal groups allows the release of therapeutics under acidic conditions, such as that of the endocytic compartments of cells, regenerating the original free polysaccharide in the end. The physical and chemical behavior of these acetal groups can be adjusted by modifying their stereoelectronic and steric properties, thereby providing materials with tunable degradation and release rates. We have applied this conjugation chemistry in the development of water-soluble siRNA carriers, namely acetal-linked amino-dextrans, with various amine structures attached through either slow- or fast-degrading acetal linker. The carriers with the best combination of amine moieties and structural composition of acetals showed high in vitro transfection efficiency and low cytotoxicity in the delivery of siRNA. © 2012 American Chemical Society.

Synthesis of novel nitroso acetal derivatives via tandem 6π-electrocyclization/ [3+2]-cycloaddition of 1-nitro-2-methyl-1,3 butadiene

OpenAIRE

Esra Koc

2017-01-01

Novel nitroso acetal derivatives (4-methyl-2,3,3a,6-tetrahydroisoxazolo[2,3-b][1,2]oxazine) were synthesized through 6π-electrocyclization/[3+2]-cycloaddition reaction of several dionophiles with 1-nitro-2-methyl-1,3-butadiene. Structures of the synthesized compounds were determined by 1H-NMR, 13C-NMR, IR and GC-MS analyses.

A theoretical study on the role of water and its derivatives in acetic acid steam reforming on Ni(111)

Science.gov (United States)

Du, Zhen-Yi; Ran, Yan-Xiong; Guo, Yun-Peng; Feng, Jie; Li, Wen-Ying

2017-10-01

Catalytic steam reforming of acetic acid can be divided into two steps, i.e. acetic acid decomposition followed by water gas shift. While theoretical studies have been devoted to these two individual reactions, the role of water and its derivatives in the reforming process, especially in CH3COOH decomposition, remains largely unknown. In this study, a thorough investigation of the effects of the solvent water and its derived O*/OH* species on some key dehydrogenation steps on Ni(111) is carried out using density functional theory. The involved dehydrogenation species include O-H bond scission species H2O*, CH3COOH*, trans-COOH* and C-H bond scission species CH3CO*, CH3C*, CH2C*. The results show that the pre-adsorbed O*, OH*, and H2O* species not only affect the adsorption stability of these species, but also influence their dehydrogenation reactivity. O* and OH* species can both enhance the O-H bond scission, and the promotional effect of O* is superior to OH*. Nevertheless, H-abstraction from C-H bond by O* and OH* are both hindered except for CH3CO* dehydrogenation in the presence of OH*. Furthermore, the solvent water notably weakens O-H bonds, yet exhibits negligible effect on the C-H bond breakage. Analogously, the solvent effect of CH3COOH* on O-H bond scission is also investigated.

Tailor-made starch-based conjugates containing well-defined poly(vinyl acetate and its derivative poly(vinyl alcohol

Directory of Open Access Journals (Sweden)

2011-06-01

Full Text Available Reversible addition-fragmentation chain transfer (RAFT polymerization was adopted to synthesize starch-based conjugates that possessed controllable architecture and properties. Starch-based xanthate agent was prepared and applied as chain transfer agent to conduct the living/controlled polymerization (LCP of vinyl acetate, which generated tailor-made conjugates of starch and well-defined poly(vinyl acetate (SVAc. The relevant derivatives, conjugates of starch and chain length-controlled poly(vinyl alcohol (SVA, were obtained subsequently. Various characterizations such as Fourier transform infrared spectra (FTIR, ultraviolet-visible spectroscopy (UV, proton nuclear magnetic resonance (1H NMR, gel permeation chromatography (GPC, X-ray diffraction (XRD, Thermogravimetric analysis (TGA, and dynamic mechanical thermal analysis (DMTA were performed to examine the structure of intermediates and the starch-based conjugates. Static contact angle measurements revealed that the hydrophilic character of starch-based conjugates was tunable. Well-defined SVAc was amphiphilic and it was able to self-assemble into size controllable micelles, which was verified by contact angles, transmission electron microscopy (TEM and dynamic light scattering (DLS tests. SVA exhibited much higher capability to form physically cross-linked hydrogel than starch did. Both the characteristic of SVAc and SVA were chain length-dependent.

Synthesis, antifungal activity and docking study of 2-amino-4H-benzochromene-3-carbonitrile derivatives

Science.gov (United States)

Mirjalili, BiBi Fatemeh; Zamani, Leila; Zomorodian, Kamiar; Khabnadideh, Soghra; Haghighijoo, Zahra; Malakotikhah, Zahra; Ayatollahi Mousavi, Seyyed Amin; Khojasteh, Shaghayegh

2016-07-01

Pathogenic fungi are associated with diseases ranging from simple dermatosis to life-threatening infections, particularly in immunocompromised patients. During the past two decades, resistance to established antifungal drugs has increased dramatically and has made it crucial to identify novel antimicrobial compounds. Here, we selected 12 new compounds of 2-amino-4H-benzochromene-3-carbonitrile drivetives (C1-C12) for synthesis by using nano-TiCl4.SiO2 as efficient and green catalyst, then nine of synthetic compounds were evaluated against different species of fungi, positive gram and negative gram of bacteria. Standard and clinical strains of antibiotics sensitive and resistant fungi and bacteria were cultured in appropriate media. Biological activity of the 2-amino-4H-benzochromene-3-carbonitrile derivatives against fungi and bacteries were estimated by the broth micro-dilution method as recommended by clinical and laboratory standard institute (CLSI). In addition minimal fangicidal and bactericial concenteration of the compounds were also determined. Considering our results showed that compound 2-amino-4-(4-methyl benzoate)-4H-benzo[f]chromen-3-carbonitrile (C9) had the most antifungal activity against Aspergillus clavatus, Candida glabarata, Candida dubliniensis, Candida albicans and Candida tropicalis at concentrations ranging from 8 to ≤128 μg/mL. Also compounds 2-amino-4-(3,4-dimethoxyphenyl)-4H-benzo[f]chromen-3-carbonitrile (C4) and 2-amino-4-(4-isopropylphenyl)-4H-benzo[f]chromen-3-carbonitrile (C3) had significant inhibitory activities against Epidermophyton floccosum following 2-amino-4-(4-methylbenzoate)-4H-benzo[f]chromen-3-carbonitrile (C9), respectively. Docking simulation was performed to insert compounds C3, C4 and C9 in to CYP51 active site to determine the probable binding model.

Co2 chemosorption by functionalized amino acid derivatives

DEFF Research Database (Denmark)

2015-01-01

The absorption and desorption behaviour of carbon dioxide (CO2) using a composition comprising an ionic compound comprising a cation [A+] and an anion [B-] is described, wherein the anion [B-] is a mono-amine functionalized amino acid.......The absorption and desorption behaviour of carbon dioxide (CO2) using a composition comprising an ionic compound comprising a cation [A+] and an anion [B-] is described, wherein the anion [B-] is a mono-amine functionalized amino acid....

Organocatalytic asymmetric michael addition of aldehydes to beta-nitroacroleine dimethyl acetal.

Science.gov (United States)

Reyes, Efraim; Vicario, Jose L; Badía, Dolores; Carrillo, Luisa

2006-12-21

[Structure: see text] The organocatalytic asymmetric Michael addition of aldehydes to beta-nitroacroleine dimethyl acetal has been studied in detail. The reaction took place with excellent yields and high stereoselectivities when a chiral beta-amino alcohol such as L-prolinol was employed as the catalyst, leaving a formation of highly functionalized enantioenriched compounds containing two differentiated formyl groups together with a nitro moiety.

Synthesis, electrochemical, spectrophotometric and potentiometric studies of two azo-compounds derived from 4-amino-2-methylquinoline in ethanolic-aqueous buffered solutions

Energy Technology Data Exchange (ETDEWEB)

El-Attar, Mona A.; Ghoneim, Mohamed M. [Analytical Chemistry Research Unit, Chemistry Department, Tanta University (Egypt); Ismail, Iqbal M., E-mail: maema.2011@yahoo.com [Chemistry Department, Faculty of Science, King Abdul Aziz University, Jeddah (Saudi Arabia)

2012-08-15

Two azo-compounds, 2-methyl-4-(5-amino-2-hydroxy-phenylazo)-quinoline (2) and 2-methyl-4-(2-hydroxy-5-nitrophenylazo)-quinoline, derived from 4-amino-2-methylquinoline were synthesized. Their chemical structures were characterized and confirmed by means of elemental chemical analysis, infrared (IR) spectroscopy, {sup 1}H nuclear magnetic resonance (NMR) and mass spectrometry (MS). The electrochemical behavior of the starting compound (4-amino-2-methylquinoline) and of the two synthesized azo-derivatives was studied at the mercury electrode in the B-R universal buffer at various pH values (2-11.5) containing 40% (v/v) ethanol using dc-polarography, cyclic voltammetry and controlled-potential coulometry. Their electrode reaction pathways were elucidated and discussed. The dissociation constants (pKa) of the examined compounds, stability constants and stoichiometry of their complexes in solution with some transition metal ions (Co(II), Ni(II), Cu(II), La(III) and UO{sup 2+}{sub 2}) were determined. (author)

Discovery of novel histidine-derived lipo-amino acids: applied in the synthesis of ultra-short antimicrobial peptidomimetics having potent antimicrobial activity, salt resistance and protease stability.

Science.gov (United States)

Ahn, Mija; Murugan, Ravichandran N; Jacob, Binu; Hyun, Jae-Kyung; Cheong, Chaejoon; Hwang, Eunha; Park, Hyo-Nam; Seo, Ji-Hyung; Srinivasrao, G; Lee, Kyung S; Shin, Song Yub; Bang, Jeong Kyu

2013-10-01

Here we report for the first time the synthesis of Histidine (His) derived lipo-amino acids having pendant lipid tails at N(τ)- and N(π)-positions on imidazole group of His and applied it into synthesis of lipo-peptides. The attachment of His-derived lipo-amino acid into the very short inactive cationic peptides endows potent antimicrobial activity against Gram-positive and Gram-negative bacteria without hemolytic activity. Furthermore, our designed His-derived lipo-peptidomimetics (HDLPs) consisting of two or three residues displayed strong anti-MRSA activity and protease stability as well as retained potent antimicrobial activity under high salt concentration. Our results demonstrate that the novel lipo-amino acid is highly flexible to synthesize and carry out the extensive structure-activity relationship (SAR) on lipo-antimicrobial peptidomimetics and represents a unique amenable platform for modifying parameters important for antimicrobial activity. Through this study, we proved that the discovery of His-derived lipo-amino acid and the corresponding HDLPs are an excellent candidate as a lead compound for the development of novel antimicrobial agents. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

Conformational Interconversions of Amino Acid Derivatives

Czech Academy of Sciences Publication Activity Database

Kaminský, Jakub; Jensen, F.

2016-01-01

Roč. 12, č. 2 (2016), s. 694-705 ISSN 1549-9618 R&D Projects: GA ČR GA13-03978S; GA ČR(CZ) GA14-03564S; GA ČR(CZ) GA16-00270S Institutional support: RVO:61388963 Keywords : amino acids * force fields * transition states Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 5.245, year: 2016

Neuromuscular electrical stimulation prior to presleep protein feeding stimulates the use of protein-derived amino acids for overnight muscle protein synthesis.

Science.gov (United States)

Dirks, Marlou L; Groen, Bart B L; Franssen, Rinske; van Kranenburg, Janneau; van Loon, Luc J C

2017-01-01

Short periods of muscle disuse result in substantial skeletal muscle atrophy. Recently, we showed that both neuromuscular electrical stimulation (NMES) as well as presleep dietary protein ingestion represent effective strategies to stimulate muscle protein synthesis rates. In this study, we test our hypothesis that NMES can augment the use of presleep protein-derived amino acids for overnight muscle protein synthesis in older men. Twenty healthy, older [69 ± 1 (SE) yr] men were subjected to 24 h of bed rest, starting at 8:00 AM. In the evening, volunteers were subjected to 70-min 1-legged NMES, while the other leg served as nonstimulated control (CON). Immediately following NMES, 40 g of intrinsically l-[1- 13 C]-phenylalanine labeled protein was ingested prior to sleep. Blood samples were taken throughout the night, and muscle biopsies were obtained from both legs in the evening and the following morning (8 h after protein ingestion) to assess dietary protein-derived l-[1- 13 C]-phenylalanine enrichments in myofibrillar protein. Plasma phenylalanine concentrations and plasma l-[1- 13 C]-phenylalanine enrichments increased significantly following protein ingestion and remained elevated for up to 6 h after protein ingestion (P protein-bound l-[1- 13 C]-phenylalanine enrichments (MPE) increased to a greater extent in the stimulated compared with the control leg (0.0344 ± 0.0019 vs. 0.0297 ± 0.0016 MPE, respectively; P protein-derived amino acids in the NMES compared with CON leg. In conclusion, application of NMES prior to presleep protein feeding stimulates the use of dietary protein-derived amino acids for overnight muscle protein synthesis in older men. Neuromuscular electrical stimulation (NMES) as well as presleep dietary protein ingestion represent effective strategies to stimulate muscle protein synthesis rates. Here we demonstrate that in older men after a day of bed rest, the application of NMES prior to presleep protein feeding stimulates the use of

Metal cation dependence of interactions with amino acids: bond dissociation energies of Rb(+) and Cs(+) to the acidic amino acids and their amide derivatives.

Science.gov (United States)

Armentrout, P B; Yang, Bo; Rodgers, M T

2014-04-24

Metal cation-amino acid interactions are key components controlling the secondary structure and biological function of proteins, enzymes, and macromolecular complexes comprising these species. Determination of pairwise interactions of alkali metal cations with amino acids provides a thermodynamic vocabulary that begins to quantify these fundamental processes. In the present work, we expand a systematic study of such interactions by examining rubidium and cesium cations binding with the acidic amino acids (AA), aspartic acid (Asp) and glutamic acid (Glu), and their amide derivatives, asparagine (Asn) and glutamine (Gln). These eight complexes are formed using electrospray ionization and their bond dissociation energies (BDEs) are determined experimentally using threshold collision-induced dissociation with xenon in a guided ion beam tandem mass spectrometer. Analyses of the energy-dependent cross sections include consideration of unimolecular decay rates, internal energy of the reactant ions, and multiple ion-neutral collisions. Quantum chemical calculations are conducted at the B3LYP, MP2(full), and M06 levels of theory using def2-TZVPPD basis sets, with results showing reasonable agreement with experiment. At 0 and 298 K, most levels of theory predict that the ground-state conformers for M(+)(Asp) and M(+)(Asn) involve tridentate binding of the metal cation to the backbone carbonyl, amino, and side-chain carbonyl groups, although tridentate binding to the carboxylic acid group and side-chain carbonyl is competitive for M(+)(Asn). For the two longer side-chain amino acids, Glu and Gln, multiple structures are competitive. A comparison of these results to those for the smaller alkali cations, Na(+) and K(+), provides insight into the trends in binding energies associated with the molecular polarizability and dipole moment of the side chain. For all four metal cations, the BDEs are inversely correlated with the size of the metal cation and follow the order Asp < Glu

Synthesis and Biological Activity of 3-[Phenyl(1,3-thiazol-2-yl-amino]propanoic Acids and Their Derivatives

Directory of Open Access Journals (Sweden)

Vytautas Mickevičius

2013-12-01

Full Text Available New N,N-disubstituted β-amino acids and their derivatives with thiazole, aromatic, and heterocyclic substituents were synthesized from N-phenyl-N-thiocarbamoyl-β-alanine by the Hantzsch method; derivatives with hydrazone fragments were also obtained. Some of the synthesized compounds exhibited discrete antimicrobial activity, and 3-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl(phenylamino]propanoic acid was found to promote rapeseed growth and to increase seed yield and oil content.

An Efficient Solid-phase Parallel Synthesis of 2-Amino and 2-Amidobenzo[d]oxazole Derivatives via Cyclization Reactions of 2-Hydroxyphenylthiourea Resin

International Nuclear Information System (INIS)

Jung, Selin; Kim, Seulgi; Lee, Geehyung; Gong, Youngdae

2012-01-01

An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]-oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo-[d]oxazole resins 4 by cyclization reaction of 2-hydroxyphenylthiourea resin 3. The resin-bound 2-hydroxy-phenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2-amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane (CH 2 Cl 2 )

Acetate Kinase Isozymes Confer Robustness in Acetate Metabolism

DEFF Research Database (Denmark)

Chan, Siu Hung Joshua; Nørregaard, Lasse; Solem, Christian

2014-01-01

transcription structure, determining enzyme characteristics and effect on growth physiology. The results show that the two ACKs are most likely individually transcribed. AckA1 has a much higher turnover number and AckA2 has a much higher affinity for acetate in vitro. Consistently, growth experiments of mutant...... physiological roles in L. lactis to maintain a robust acetate metabolism for fast growth at different extracellular acetate concentrations. The existence of ACK isozymes may reflect a common evolutionary strategy in bacteria in an environment with varying concentrations of acetate.......Acetate kinase (ACK) (EC no: 2.7.2.1) interconverts acetyl-phosphate and acetate to either catabolize or synthesize acetyl-CoA dependent on the metabolic requirement. Among all ACK entries available in UniProt, we found that around 45% are multiple ACKs in some organisms including more than 300...

Sorption and Microbial Uptake of Alanine, Glucose and Acetate in Soil

Science.gov (United States)

Fischer, H.; Ingwersen, J.; Kuzyakov, Y.

2009-04-01

Low molecular weight organic substances (LMWOS), e. g. amino acids, sugars, and carboxylic acids, are C compounds that are most rapidly turned-over in the C cycle of soil. Despite of their importance it is still unknown how sorption to the soil matrix affects their turnover in soil solution. The goals of this study were (1) to describe the dynamics of the fluxes of LMWOS (10 µmol l-1) in various pools (dissolved, adsorbed, decomposed to CO2, incorporated into microbial biomass) and (2) to assess the LMWOS distribution in these pools in dependence of very wide range of concentration (0.01 to 1000 µmol l-1). Representatives of each LMWOS group (glucose for sugars, alanine for amino acids, Na-acetate for carboxylic acids) uniformly labeled with 14C were added to sterilized or non-sterilized soil and analyzed in dif-ferent compartments between 1 min and 5.6 hours after addition. LMWOS were almost completely taken up by microorganisms within the first 30 min. Microbial uptake was much faster than the physicochemical sorption (estimated in sterilized soil), which needed to reach quasi-equilibrium 60 min for alanine and about 400 min for glucose. Only sorption of acetate was instantaneous (>1 min). While for acetate the maximum sorption capacity was reached at 100 µmol l-1 no such maximum was found for glucose and alanine in the studied concentra-tion range. At the concentration of 100 µmol l-1, microbial decomposition after 4.5 h hours was higher for alanine (76.7±1.1%) than acetate (55.2±0.9%) and glucose (28.5±1.5%). On the contrary, incorporation into microbial biomass was higher for glucose (59.8±1.2%) than for acetate (23.4±5.9%) and alanine (5.2±2.8%). Within 10 to 500 µmol l-1 the pathways of the three LMWOS transformation changed: at 500 µmol l-1 alanine and acetate were less mineralized and more incorporated into microbial biomass than at 10 µmol l-1, while glucose incorporation decreased. Consequently, the concentrations of alanine, glucose, and

Mycosporine like amino acids in brown algae

OpenAIRE

Serban Radu; Stoian Gheorghe

2013-01-01

Biosynthesis of mycosporine and accumulation in cells serves as protection, by shielding the cells sensitive molecules Mycosporine-like aminoacids (MAAs) are derivated compounds of mycosporine that contains an amino-cyclohexenimine ring liked to an amino acid, amino alcohol or amino group. They preesent absorbtion maximum between 320 and 360 nm.

Determination of amino acid neurotransmitters in rat hippocampi by HPLC-UV using NBD-F as a derivative.

Science.gov (United States)

Wu, Xiaomeng; Wang, Rui; Jiang, Qingqing; Wang, Shue; Yao, Yao; Shao, Lihua

2014-04-01

A simple, rapid and accurate high-performance liquid chromatography method with ultraviolet-visible detection was developed for the determination of five amino acid neurotransmitters - aspartate, glutamic acid, glycine, taurine and γ-aminobutyric acid - in rat hippocampi with pre-column derivatization with 4-fluoro-7-nitrobenzofurazan. Several conditions which influenced derivatization and separation, such as pH, temperature, acetonitrile percentage mobile phase and flow rate, were optimized to obtain a suitable protocol for amino acids quantification in samples. The separation of the five neurotransmitter derivatives was performed on a C18 column using a mobile phase consisting of phosphate buffer (0.02 mol/L, pH 6.0)-acetonitrile (84:16, v/v) at a flow rate of 1.0 mL/min with the column temperature at 30°C. The detection wavelength was 472 nm. Without gradient elution, the five neurotransmitter derivatives were completely separated within 15 min. The linear relation was good in the range from 0.50 to 500 µmol/L, and the correlation coefficients were ≥0.999. Intra-day precision was between 1.8 and 3.2%, and inter-day precision was between 2.4 and 4.7%. The limits of detection (signal-to-noise ratio 3) were from 0.02 to 0.15 µmol/L. The established method was used to determine amino acid neurotransmitters in rat hippocampi with satisfactory recoveries varying from 94.9 to 105.2%. Copyright © 2013 John Wiley & Sons, Ltd.

Synthesis and antimicrobial activities of new higher amino acid Schiff base derivatives of 6-aminopenicillanic acid and 7-aminocephalosporanic acid

Science.gov (United States)

Özdemir (nee Güngör), Özlem; Gürkan, Perihan; Özçelik, Berrin; Oyardı, Özlem

2016-02-01

Novel β-lactam derivatives (1c-3c) (1d-3d) were produced by using 6-aminopenicillanic acid (6-APA), 7-aminocephalosporanic acid (7-ACA) and the higher amino acid Schiff bases. The synthesized compounds were characterized by elemental analysis, IR, 1H/13C NMR and UV-vis spectra. Antibacterial activities of all the higher amino acid Schiff bases (1a-3a) (1b-3b) and β-lactam derivatives were screened against three gram negative bacteria (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Acinetobacter baumannii RSKK 02026), three gram positive bacteria (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 07005, Bacillus subtilis ATCC 6633) and their drug-resistant isolates by using broth microdilution method. Two fungi (Candida albicans and Candida krusei) were used for antifungal activity.

Mycosporine like amino acids in brown algae

Directory of Open Access Journals (Sweden)

Serban Radu

2013-12-01

Full Text Available Biosynthesis of mycosporine and accumulation in cells serves as protection, by shielding the cells sensitive molecules Mycosporine-like aminoacids (MAAs are derivated compounds of mycosporine that contains an amino-cyclohexenimine ring liked to an amino acid, amino alcohol or amino group. They preesent absorbtion maximum between 320 and 360 nm.

Biphasic kinetics in the reaction between amino acids or glutathione and the chromium acetate cluster, [Cr3O(OAc)6]+.

Science.gov (United States)

Chaudhary, Shveta; Van Horn, J David

2006-11-07

Kinetics for the breakdown of the trinuclear chromium acetate cluster with a series of monoprotic and diprotic amino acid ligands and with glutathione in aqueous media have been investigated spectrophotometrically at pH 3.5-5.5 and in a temperature range of 45-60 degrees C. Under pseudo-first-order conditions, reactions with these ligands exhibited biphasic kinetic behavior that can be accounted for by a consecutive two-step reaction, A-->B-->C, where A is assumed to be a forced ion pair, B an intermediate and C is the product; experimental data fit to a biexponential equation for the transformation. Rates for k(short), k(long), and k(obs) were determined by manual extrapolation of absorbance data or curve-fitting routines; associated activation parameters for each step of the reaction were calculated using the Eyring equation. Rates for the first and second steps of the reaction are on the order of approximately 10(-4) and approximately 10(-5)s(-1), respectively. The large negative values of DeltaS++ and smaller DeltaH++ in the first step indicate an associative step, while high positive values of DeltaS(double dagger) in the second step indicate dissociation. To account for the results mechanistically, the results are interpreted to be a first step of ligand exchange with a pseudo-axial aqua ligand, followed by a dissociative step involving acetate or oxo ligand displacement. The dissociative step is the rate determining step, with k(obs) approximately k(long). The results demonstrate reaction pathways that are available to the Cr(III) metal centers that may be physiologically relevant in the ligand-rich environment of biological systems. Under general conditions Cr(III) clusters may be expected to be broken down, unless some unique biological environment stabilizes the cluster. The present study has application to the processes related to Cr(III) transport and excretion, to potential mechanisms of Cr(III) action in a biological setting, and to the

Ultrasound mediated, iodine catalyzed green synthesis of novel 2-amino-3-cyano-4H-pyran derivatives.

Science.gov (United States)

Tabassum, Sumaiya; Govindaraju, Santhosh; Khan, Riyaz-ur-Rahaman; Pasha, Mohamed Afzal

2015-05-01

An efficient synthesis of a novel series of twelve substituted 2-amino-3-cyano-4H-pyran derivatives was achieved by a one-pot three-component cyclocondensation reaction of heteroaryl aldehydes, malononitrile and active methylene compounds catalyzed by iodine in aqueous medium under ultrasound irradiation. In comparison with conventional methods, our protocol is convenient and offers several advantages, such as shorter reaction time, higher yields, milder conditions and environmental friendliness. We have herein successfully demonstrated the synergistic outcome of multi-component reaction (MCR) and sonication to offer a facile route for the design of these derivatives. Copyright © 2014 Elsevier B.V. All rights reserved.

Selection of protease for increased solubilization of protein-derived thiols during mashing with limited release of free amino acids in beer

DEFF Research Database (Denmark)

Murmann, Anne Nordmark; Lunde, Christina; Lund, Marianne Nissen

2016-01-01

Extraction of protein-derived thiols by protease treatment during mashing for improvement of flavor stability in beer has previously been shown to cause concomitant increase in free amino acid concentrations and thereby increased levels of unwanted Maillard reaction products during aging. The pre......Extraction of protein-derived thiols by protease treatment during mashing for improvement of flavor stability in beer has previously been shown to cause concomitant increase in free amino acid concentrations and thereby increased levels of unwanted Maillard reaction products during aging...... of a protease with a higher temperature optimum dosed at only 3 mg of enzyme/kg of malt, it is possible to increase thiol concentrations in wort by 30% and with only a maximum 10% increase in amino acid concentration compared with a control. Pilot brewing showed that beer brewed with addition of protease...... stability during storage could not be evaluated. Overall, similar brewing and sensory characteristics were obtained compared with a control beer brewed without addition of protease. Foam stability was decreased by protease treatment, and formation of haze was reduced by protease treatment....

Synthesis and Biological Activity of Novel Amino Acid-(N'-Benzoyl Hydrazide and Amino Acid-(N'-Nicotinoyl Hydrazide Derivatives

Directory of Open Access Journals (Sweden)

Sherine N. Khattab

2005-09-01

Full Text Available The coupling reaction of benzoic acid and nicotinic acid hydrazides with N- protected L-amino acids including valine, leucine, phenylalanine, glutamic acid and tyrosine is reported. The target compounds, N-Boc-amino acid-(N`-benzoyl- and N- Boc-amino acid-(N`-nicotinoyl hydrazides 5a-5e and 6a-6e were prepared in very high yields and purity using N-[(dimethylamino-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl- methylene]-N-methyl-methanaminium hexafluorophosphate N-oxide (HATU as coupling reagent. The antimicrobial activity of the Cu and Cd complexes of the designed compounds was tested. The products were deprotected affording the corresponding amino acid-(N`-benzoyl hydrazide hydrochloride salts (7a-7e and amino acid-(N`- nicotinoyl hydrazide hydrochloride salts (8a-8e. These compounds and their Cu and Cd complexes were also tested for their antimicrobial activity. Several compounds showed comparable activity to that of ampicillin against S. aureus and E. coli.

Excitatory amino acid receptor antagonists

DEFF Research Database (Denmark)

Johansen, T N; Frydenvang, Karla Andrea; Ebert, B

1997-01-01

We have previously shown that (RS)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA) is an antagonist at N-methyl-D-aspartic acid (NMDA) and (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptors. We have now resolved ATAA via diastereomeric salt formation......)-phenylethylamine salt of N-BOC-(R)-ATAA. Like ATAA, neither (R)- nor (S)-ATAA significantly affected (IC50 > 100 microM) the receptor binding of tritiated AMPA, kainic acid, or (RS)-3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid, the latter being a competitive NMDA antagonist. Electrophysiological experiments......, using the rat cortical wedge preparation, showed the NMDA antagonist effect as well as the AMPA antagonist effect of ATAA to reside exclusively in the (R)-enantiomer (Ki = 75 +/- 5 microM and 57 +/- 1 microM, respectively). Neither (R)- nor (S)-ATAA significantly reduced kainic acid-induced excitation...

Methanogenesis from acetate by Methanosarcina barkeri: Catalysis of acetate formation from methyl iodide, CO/sub 2/, and H/sub 2/ by the enzyme system involved

Energy Technology Data Exchange (ETDEWEB)

Laufer, K; Eikmanns, B; Frimmer, U; Thauer, R K

1987-04-01

Cell suspensions of Methanosarcina barkeri grown on acetate catalyze the formation of methane and CO/sub 2/ from acetate as well as an isotopic exchange between the carboxyl group of acetate and CO/sub 2/. Here we report that these cells also mediate the synthesis of acetate from methyl iodide, CO/sub 2/, and reducing equivalents (H/sub 2/ or CO), the methyl group of acetate being derived from methyl iodide and the carboxyl group from CO/sub 2/. Methyl chloride and methyltosylate but not methanol can substitute for methyl iodide in this reaction. Acetate formation from methyl iodide, CO/sub 2/, and reducing equivalents is coupled with the phosphorylation of ADP. Evidence is presented that methyl iodide is incorporated into the methyl group of acetate via a methyl corrinoid intermediate (deduced from inhibition experiments with propyl iodide) and that CO/sub 2/ is assimilated into the carboxyl group via a C/sub 1/ intermediate which does not exchange with free formate or free CO. The effects of protonophores, of the proton-translocating ATPase inhibitor N,N'-dicyclohexylcarbodiimide, and of arsenate on acetate formation are interpreted to indicate that the reduction of CO/sub 2/ to the oxidation level of the carboxyl group of acetate requires the presence of an electrochemical proton potential and that acetyl-CoA or acetyl-phosphate rather than free acetate is the immediate product of the condensation reaction. These results are dicsussed with respect to the mechanism of methanogenesis from acetate.

OxymaPure/DIC: An Efficient Reagent for the Synthesis of a Novel Series of 4-[2-(2-Acetylaminophenyl-2-oxo-acetylamino] Benzoyl Amino Acid Ester Derivatives

Directory of Open Access Journals (Sweden)

Ayman El-Faham

2013-11-01

Full Text Available OxymaPure (ethyl 2-cyano-2-(hydroxyiminoacetate was tested as an additive for use in the carbodiimide (DIC approach for the synthesis of a novel series of α-ketoamide derivatives (4-[2-(2-acetylaminophenyl-2-oxo-acetylamino]benzoyl amino acid ester derivatives. OxymaPure showed clear superiority to HOBt/DIC or carbodiimide alone in terms of purity and yield. The title compounds were synthesized via the ring opening of N-acylisatin. First, N-acetylisatin was reacted with 4-aminobenzoic acid under conventional heating as well as microwave irradiation to afford 4-(2-(2-acetamidophenyl-2-oxoacetamidobenzoic acid. This α-ketoamide was coupled to different amino acid esters using OxymaPure/DIC as a coupling reagent to afford 4-[2-(2-acetylaminophenyl-2-oxo-acetylamino]benzoyl amino acid ester derivatives in excellent yield and purity. The synthesized compounds were characterized using FT-IR, NMR, and elemental analysis.

Library of Antifouling Surfaces Derived From Natural Amino Acids by Click Reaction.

Science.gov (United States)

Xu, Chen; Hu, Xin; Wang, Jie; Zhang, Ye-Min; Liu, Xiao-Jiu; Xie, Bin-Bin; Yao, Chen; Li, Yi; Li, Xin-Song

2015-08-12

Biofouling is of great concern in numerous applications ranging from ophthalmological implants to catheters, and from bioseparation to biosensors. In this report, a general and facile strategy to combat surface fouling is developed by grafting of amino acids onto polymer substrates to form zwitterionic structure through amino groups induced epoxy ring opening click reaction. First of all, a library of poly(2-hydroxyethyl methacrylate-co-glycidyl methacrylate) hydrogels with zwitterionic surfaces were prepared, resulting in the formation of pairs of carboxyl anions and protonated secondary amino cations. The analysis of attenuated total reflectance Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy confirmed the successful immobilization of amino acids on the hydrogel surfaces. After that, the contact angle and equilibrium water content of the modified hydrogels showed that the hydrogels exhibited improved hydrophilicity compared with the parent hydrogel. Furthermore, the protein deposition was evaluated by bicinchoninic acid assay using bovine serum albumin (BSA) and lysozyme as models. The results indicated that the performance of the hydrogels was determined by the nature of incorporated amino acid: the hydrogels incorporated with neutral amino acids had nonspecific antiadsorption capability to both BSA and lysozyme; the hydrogels incorporated with charged amino acids showed antiadsorption behaviors against protein with same charge and enhanced adsorption to the protein with opposite charge; the optimal antiadsorption performance was observed on the hydrogels incorporated with polar amino acids with a hydroxyl residual. The improvement of antiprotein fouling of the neutral amino acids grafted hydrogels can be ascribed to the formation of zwitterionic surfaces. Finally, a couple of soft contact lenses grafted with amino acids were fabricated having improved antifouling property and hydrophilicity. The result demonstrated the success of

Isolation of acetic, propionic and butyric acid-forming bacteria from biogas plants.

Science.gov (United States)

Cibis, Katharina Gabriela; Gneipel, Armin; König, Helmut

2016-02-20

In this study, acetic, propionic and butyric acid-forming bacteria were isolated from thermophilic and mesophilic biogas plants (BGP) located in Germany. The fermenters were fed with maize silage and cattle or swine manure. Furthermore, pressurized laboratory fermenters digesting maize silage were sampled. Enrichment cultures for the isolation of acid-forming bacteria were grown in minimal medium supplemented with one of the following carbon sources: Na(+)-dl-lactate, succinate, ethanol, glycerol, glucose or a mixture of amino acids. These substrates could be converted by the isolates to acetic, propionic or butyric acid. In total, 49 isolates were obtained, which belonged to the phyla Firmicutes, Tenericutes or Thermotogae. According to 16S rRNA gene sequences, most isolates were related to Clostridium sporosphaeroides, Defluviitoga tunisiensis and Dendrosporobacter quercicolus. Acetic, propionic or butyric acid were produced in cultures of isolates affiliated to Bacillus thermoamylovorans, Clostridium aminovalericum, Clostridium cochlearium/Clostridium tetani, C. sporosphaeroides, D. quercicolus, Proteiniborus ethanoligenes, Selenomonas bovis and Tepidanaerobacter sp. Isolates related to Thermoanaerobacterium thermosaccharolyticum produced acetic, butyric and lactic acid, and isolates related to D. tunisiensis formed acetic acid. Specific primer sets targeting 16S rRNA gene sequences were designed and used for real-time quantitative PCR (qPCR). The isolates were physiologically characterized and their role in BGP discussed. Copyright © 2016 Elsevier B.V. All rights reserved.

In situ synthesis, electrochemical and quantum chemical analysis of an amino acid-derived ionic liquid inhibitor for corrosion protection of mild steel in 1M HCl solution

International Nuclear Information System (INIS)

Kowsari, E.; Arman, S.Y.; Shahini, M.H.; Zandi, H.; Ehsani, A.; Naderi, R.; PourghasemiHanza, A.; Mehdipour, M.

2016-01-01

Highlights: • Electrochemical analysis of effectiveness of an amino acid-derived ionic liquid inhibitor. • Quantum chemical analysis of effectiveness of an amino acid-derived ionic liquid inhibitor. • Finding correlation between electrochemical analysis and quantum chemical analysis. - Abstract: In this study, an amino acid-derived ionic liquid inhibitor, namely tetra-n-butyl ammonium methioninate, was synthesized and the role this inhibitor for corrosion protection of mild steel exposed to 1.0 M HCl was investigated using electrochemical, quantum and surface analysis. By taking advantage of potentiodynamic polarization, the inhibitory action of tetra-n-butyl ammonium methioninate was found to be mainly mixed-type with dominant anodic inhibition. The effectiveness of the inhibitor was also indicated using electrochemical impedance spectroscopy (EIS). Moreover, to provide further insight into the mechanism of inhibition, electrochemical noise (EN) and quantum chemical calculations of the inhibitor were performed.

Synthesis of Water-Soluble Amino Functionalized Multithiacalix[4]arene via Quaternization of Tertiary Amino Groups

Directory of Open Access Journals (Sweden)

Roman Nosov

2018-05-01

Full Text Available A convenient approach to the synthesis of multithiacalix[4]arene derivatives containing amino groups and phthalimide fragments by the formation of quaternary ammonium salts is presented. As the initial macrocycle for the synthesis of multithiacalix[4]arenes, a differently substituted p-tert-butylthiacalix[4]arene containing bromoacetamide and three phthalimide fragments was used in a 1,3-alternate conformation. The macrocycle in cone conformation containing the tertiary amino groups was found to be a convenient core for the multithiacalix[4]arene systems. Interaction of the core multithiacalix[4]arene with monobromoacetamide derivatives of p-tert-butylthiacalix[4]arene resulted in formation in high yields of pentakisthiacalix[4]arene containing quaternary ammonium and phthalimide fragments. The removal of phthalimide groups led to the formation of amino multithiacalix[4]arene in a good yield. Based on dynamic light scattering, it was shown that the synthesized amino multithiacalix[4]arene, with pronounced hydrophobic and hydrophilic fragments, formed dendrimer-like nanoparticles in water via direct supramolecular self-assembly.

Amino acids and glycine ethyl ester as new crystallization reagents for lysozyme

International Nuclear Information System (INIS)

Ito, Len; Shiraki, Kentaro; Yamaguchi, Hiroshi

2010-01-01

During the past two decades, amino acids and amino-acid derivatives have been applied in various fields of protein chemistry. The potential use of amino acids and their derivatives as new precipitating agents is described. Several amino acids and their derivatives are prominent additives in the field of protein chemistry. This study reports the use of charged amino acids and glycine ethyl ester as precipitants in protein crystallization, using hen egg-white lysozyme (HEWL) as a model. A discussion of the crystallization of HEWL using these reagents as precipitating agents is given

Amino acid metabolism of Lemna minor L

International Nuclear Information System (INIS)

Rhodes, D.; Rich, P.J.; Brunk, D.G.

1989-01-01

A serious limitation to the use of N(O,S)-heptafluorobutyryl isobutyl amino acid derivatives in the analysis of 15 N-labeling kinetics of amino acids in plant tissues, is that the amides glutamine and asparagine undergo acid hydrolysis to glutamate and aspartate, respectively, during derivatization. This led us to consider an alternative procedure for derivatization of glutamine and asparagine with N-methyl-N-(tert-butyldimethylsilyl)-trifluoroacetamide in pyridine. Gas chromatography-mass spectrometry yielded fragment ions (M-57) of mass 417 and 431 for the [ 14 N]asparagine and [ 14 N]glutamine derivatives, respectively, suitable for monitoring unlabeled, single- 15 N- and double- 15 N-labeled amide species from the ion clusters at mass to charge ratio (m/z) 415 to 423 for asparagine, and m/z 429 to 437 for glutamine. From separate analyses of the specific isotope abundance of the amino-N groups of asparagine and glutamine as their N-heptafluorobutyryl isobutyl derivatives, the specific amide-[ 15 N] abundance of these amino acids was determined

Synthesis of novel 4,6-di(substituted)amino-1,2-dihydro-1,3,5-triazine derivatives as topical antiseptic agents.

Science.gov (United States)

Maeda, Shirou; Kita, Toshiko; Meguro, Kanji

2009-02-12

A series of novel 4,6-di(substituted)amino-1,2-dihydro-1,3,5-triazine derivatives designed to have ClogP of 5.1-7.5 was synthesized and evaluated for their antiseptic properties by MIC and MBC tests against Gram-positive and Gram-negative bacteria, including MRSA, VRE, and P. aeruginosa. Among these compounds, 4-alkyl-6-aralkyl derivatives having ClogP of 6.6-7.1 and 4-alkyl-6-aryl or 4,6-dialkyl derivatives with ClogP of 6.0-6.4 showed pronounced antibacterial activities in both tests.

Copper(I) mediated cross-coupling of amino acid derived organozinc reagents with acid chlorides

DEFF Research Database (Denmark)

Hjelmgaard, Thomas; Tanner, David Ackland

2006-01-01

This paper describes the development of a straightforward experimental protocol for copper-mediated cross-coupling of amino acid derived beta-amido-alkylzinc iodides 1 and 3 with a range of acid chlorides. The present method uses CuCN center dot 2LiCl as the copper source and for organozinc reagent...... 1 the methodology appears to be limited to reaction with more stable acid chlorides, providing the desired products in moderate yields. When applied to organozinc reagent 3, however, the protocol is more general and provides the products in good yields in all but one of the cases tested....

N9-Substituted N(6)-[(3-methylbut-2-en-1-yl)amino]purine derivatives and their biological activity in selected cytokinin bioassays

Czech Academy of Sciences Publication Activity Database

Mik, V.; Szüčová, Lucie; Spíchal, Lukáš; Plíhal, O.; Nisler, Jaroslav; Zahajská, L.; Doležal, Karel; Strnad, Miroslav

2011-01-01

Roč. 19, č. 23 (2011), s. 7244-7251 ISSN 0968-0896 R&D Projects: GA MŠk ED0007/01/01; GA ČR GA522/09/1576 Keywords : N6-[(3-Methylbut-2-en-1-yl)amino]purine * Isopentenyladenine derivatives * N9-Substituted derivatives * Cytokinins * Cytokinin receptors Subject RIV: EF - Botanics Impact factor: 2.921, year: 2011

BF2 complex of fluorinated dipyrrolyldiketone: a new class of efficient receptor for acetate anions.

Science.gov (United States)

Maeda, Hiromitsu; Ito, Yoshihiro

2006-10-02

The beta-fluorinated derivative (2b) of the 1,3-dipyrrolyl-1,3-propanedione BF2 complex has been prepared from 3,4-difluoropyrrole and malonyl chloride, followed by treatment with BF3.OEt2. Despite the simple, acyclic, and neutral structure, 2b exhibits efficient 1:1 binding for anions in CH2Cl2 using the bridging CH and pyrrole NH as interaction sites. The binding constant (Ka) of 2b for acetate (CH3CO(2-)), associating more effectively than anions such as F-, Cl-, Br-, H2PO(4-), and HSO(4-), is estimated to be 9.6 x 10(5) M(-1), approximately 9 times larger than that of the beta-H derivative 2a (1.1 x 10(5) M(-1)). The UV-vis and fluorescence spectral changes of 2b elucidate the effective recognition of an amino acid, such as phenylalanine, in the anionic form; this is also supported by CD spectral changes with mirror images by L- and D-isomers. Furthermore, in the solid state, BF2 complex 2b provides Cl- -bridged supramolecular networks and, in sharp contrast, deprotonated "anionic" self-assembled structures by F- binding.

Development of short and highly potent self-assembling elastin-derived pentapeptide repeats containing aromatic amino acid residues.

Science.gov (United States)

Taniguchi, Suguru; Watanabe, Noriko; Nose, Takeru; Maeda, Iori

2016-01-01

Tropoelastin is the primary component of elastin, which forms the elastic fibers that make up connective tissues. The hydrophobic domains of tropoelastin are thought to mediate the self-assembly of elastin into fibers, and the temperature-mediated self-assembly (coacervation) of one such repetitive peptide sequence (VPGVG) has been utilized in various bio-applications. To elucidate a mechanism for coacervation activity enhancement and to develop more potent coacervatable elastin-derived peptides, we synthesized two series of peptide analogs containing an aromatic amino acid, Trp or Tyr, in addition to Phe-containing analogs and tested their functional characteristics. Thus, position 1 of the hydrophobic pentapeptide repeat of elastin (X(1)P(2)G(3)V(4)G(5)) was substituted by Trp or Tyr. Eventually, we acquired a novel, short Trp-containing elastin-derived peptide analog (WPGVG)3 with potent coacervation ability. From the results obtained during this process, we determined the importance of aromaticity and hydrophobicity for the coacervation potency of elastin-derived peptide analogs. Generally, however, the production of long-chain synthetic polypeptides in quantities sufficient for commercial use remain cost-prohibitive. Therefore, the identification of (WPGVG)3, which is a 15-mer short peptide consisting simply of five natural amino acids and shows temperature-dependent self-assembly activity, might serve as a foundation for the development of various kinds of biomaterials. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.

Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins

KAUST Repository

Millet, Anthony

2016-06-20

A tin- and halide-free, visible-light photoredox-catalyzed Giese reaction was developed. Primary and secondary α-amino radicals were generated readily from amino acids in the presence of catalytic amounts of an iridium photocatalyst. The reactivity of the α-amino radicals has been evaluated for the functionalization of a variety of activated olefins. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins

KAUST Repository

Millet, Anthony; Lefebvre, Quentin; Rueping, Magnus

2016-01-01

A tin- and halide-free, visible-light photoredox-catalyzed Giese reaction was developed. Primary and secondary α-amino radicals were generated readily from amino acids in the presence of catalytic amounts of an iridium photocatalyst. The reactivity of the α-amino radicals has been evaluated for the functionalization of a variety of activated olefins. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Ligand exchange chromatography for analysis and preparative separation of tritium-labelled amino acids

International Nuclear Information System (INIS)

Zolotarev, Yu.A.; Zaitsev, D.A.; Penkina, V.I.; Dostavalov, I.N.; Myasoedov, N.F.

1988-01-01

Racemic tritium-labelled amino acids were separated into optical isomers by chromatography on a chiral polyacrylamide sorbent filled with copper ions. The polyacrylamide sorbent is synthesized by Mannich's reaction through the action of formaldehyde and L-phenylalanine upon polyacrylamide Biogel P-4 in an alkali phosphate buffer. Tritium-labelled amino acids are eluted by a weak alkali solution of ammonium carbonate. Data are presented on the ligand exchange chromatography of amino acids depending on the degree to which the sorbent is filled with copper ions and on the eluent concentration. Amino acids are isolated from the eluent on short columns filled with sulfonated cation exchanger in the H + form. HPLC on modified silica gel sorbents is also used for the analysis of tritium-labelled optically active amino acids. Amino acids are eluted by a weakly acidic water-methanol solution containing ammonium acetate. UV and scintillation flow type detectors are used. (author) 7 refs.; 8 figs

Esterification from derivates of styrene by acetic acid using perchloric acid as a catalyzer; Esterificacion de derivados de estireno con acido acetico en presencia de acido perclorico como catalizador

Energy Technology Data Exchange (ETDEWEB)

Martinez de la Cuesta, P.J.; Rus Martinez, E.; Palomino sosa, R.; Palomino Perez, F. I. [Departamento deIngenieria Quimica, Facultad de Ciencias, Universidad de Malaga, Malaga (Spain)

1995-11-01

The present work is focused to develop the production of esters from derivatives of styrene by acetic acid using perchloric acid as a catalyst. The kinetics of the reaction was studied and analysis of the variables was carried out. 18 refs.

Synthesis of L-2-amino-8-oxodecanoic acid: an amino acid component of apicidins

OpenAIRE

Linares de la Morena, María Lourdes; Agejas Chicharro, Francisco Javier; Alajarín Ferrández, Ramón; Vaquero López, Juan José; Álvarez-Builla Gómez, Julio

2001-01-01

The synthesis Of L-2-amino-8-oxodecanoic acid (Aoda) is described. This is a rare amino acid component of apicidins, a family of new cyclic tetrapeptides, inhibitors of histone deacetylase. Aoda was synthesised in seven steps from L-glutamic acid along with some derivatives. Universidad de Alcalá Fundación General de la Universidad de Alcalá FEDER

Catalytic amino acid production from biomass-derived intermediates

KAUST Repository

Deng, Weiping; Wang, Yunzhu; Zhang, Sui; Gupta, Krishna M.; Hü lsey, Max J.; Asakura, Hiroyuki; Liu, Lingmei; Han, Yu; Karp, Eric M.; Beckham, Gregg T.; Dyson, Paul J.; Jiang, Jianwen; Tanaka, Tsunehiro; Wang, Ye; Yan, Ning

2018-01-01

Amino acids are the building blocks for protein biosynthesis and find use in myriad industrial applications including in food for humans, in animal feed, and as precursors for bio-based plastics, among others. However, the development of efficient

The Key to Acetate: Metabolic Fluxes of Acetic Acid Bacteria under Cocoa Pulp Fermentation-Simulating Conditions

Science.gov (United States)

Adler, Philipp; Frey, Lasse Jannis; Berger, Antje; Bolten, Christoph Josef; Hansen, Carl Erik

2014-01-01

Acetic acid bacteria (AAB) play an important role during cocoa fermentation, as their main product, acetate, is a major driver for the development of the desired cocoa flavors. Here, we investigated the specialized metabolism of these bacteria under cocoa pulp fermentation-simulating conditions. A carefully designed combination of parallel 13C isotope labeling experiments allowed the elucidation of intracellular fluxes in the complex environment of cocoa pulp, when lactate and ethanol were included as primary substrates among undefined ingredients. We demonstrate that AAB exhibit a functionally separated metabolism during coconsumption of two-carbon and three-carbon substrates. Acetate is almost exclusively derived from ethanol, while lactate serves for the formation of acetoin and biomass building blocks. Although this is suboptimal for cellular energetics, this allows maximized growth and conversion rates. The functional separation results from a lack of phosphoenolpyruvate carboxykinase and malic enzymes, typically present in bacteria to interconnect metabolism. In fact, gluconeogenesis is driven by pyruvate phosphate dikinase. Consequently, a balanced ratio of lactate and ethanol is important for the optimum performance of AAB. As lactate and ethanol are individually supplied by lactic acid bacteria and yeasts during the initial phase of cocoa fermentation, respectively, this underlines the importance of a well-balanced microbial consortium for a successful fermentation process. Indeed, AAB performed the best and produced the largest amounts of acetate in mixed culture experiments when lactic acid bacteria and yeasts were both present. PMID:24837393

Improved adaptation of test with lanthanum nitrate for the colorimetric estimation of acetate

Energy Technology Data Exchange (ETDEWEB)

Szumilo, T [Akademia Medyczna, Lublin (Poland)

1976-01-01

A colorimetric method for the determination of acetate based on the production of the blue complex between iodine and lanthanum alkaline acetate has been developed. Optimum concentrations of reagents (acetate, lanthanum nitrate, iodine and ammonia) as well as the volume of acetate were selected to achieve best colour intensity. Coloured complex was stabilized by dilution of reagent mixture with water to the final volume convenient for determinaton. Absorbance of the complex can be measured immediately after dilution and any changes can be observed during at least 15 minutes. Elevation of temperature over 60/sup 0/decreases absorbance. The method fulfills the Beer's law in the range 1,5-3,5 ..mu..moles of acetate, precision of the method 2/sup +/ = 3,7%. Apart from acetate - propionate and fluoroacetate complex is 620 nm, propionate complex - at 590 nm. Propionate complex displayed any relationship between concentration and absorbance. Potassium, sodium, lithium and barium acetates give the identical results as acetic acid, whereas zinc and cupric acetates failed to react. Other derivatives tested, e.g. chloroacetate, trichloroacetate, iodoacetate, chloroporpionate and butyrate are unable to form the coloured complexes. Many compounds interfere with the formation of acetate complex, therefore, in material containing impurities acetate can be determined after purificaton by means of described in literature methods.

EXTRACTION-CHROMATOGRAPHIC DETERMINATION OF GLUCOSE AND FRUCTOSE IN THE PRESENCE OF AROMATIC AMINO ACIDS

Directory of Open Access Journals (Sweden)

Y. I. Korenman

2012-01-01

Full Text Available The extraction of glucose and fructose from aqueous salt solutions containing aromatic amino acids (phenylalanine, tryptophan, tyrosine, hydrophilic solvents (aliphatic alcohols, alkyl acetates, ketones have been studied. The quantitative characteric of the process (the distribution coefficients, the degree of extraction, separation factors are calculeted. The dependence of distribution ratios of monosaccharides from the amino acid content in the solution has been established. A mobile phase for analysis of the concentrate by ascending thin layer chromatography have been developed.

Aristolochic acid and its derivatives as inhibitors of snake venom L-amino acid oxidase.

Science.gov (United States)

Bhattacharjee, Payel; Bera, Indrani; Chakraborty, Subhamoy; Ghoshal, Nanda; Bhattacharyya, Debasish

2017-11-01

Snake venom L-amino acid oxidase (LAAO) exerts toxicity by inducing hemorrhage, pneumorrhagia, pulmonary edema, cardiac edema, liver cell necrosis etc. Being well conserved, inhibitors of the enzyme may be synthesized using the template of the substrate, substrate binding site and features of the catalytic site of the enzyme. Previous findings showed that aristolochic acid (AA), a major constituent of Aristolochia indica, inhibits Russell's viper venom LAAO enzyme activity since, AA interacts with DNA and causes genotoxicity, derivatives of this compound were synthesized by replacing the nitro group to reduce toxicity while retaining the inhibitory potency. The interactions of AA and its derivatives with LAAO were followed by inhibition kinetics and surface plasmon resonance. Similar interactions with DNA were followed by absorption spectroscopy and atomic force microscopy. LAAO-induced cytotoxicity was evaluated by generation of reactive oxygen species (ROS), cell viability assays, confocal and epifluorescence microscopy. The hydroxyl (AA-OH) and chloro (AA-Cl) derivatives acted as inhibitors of LAAO but did not interact with DNA. The derivatives significantly reduced LAAO-induced ROS generation and cytotoxicity in human embryonic kidney (HEK 293) and hepatoma (HepG2) cell lines. Confocal images indicated that AA, AA-OH and AA-Cl interfered with the binding of LAAO to the cell membrane. AA-OH and AA-Cl significantly inhibited LAAO activity and reduced LAAO-induced cytotoxicity. Copyright © 2017 Elsevier Ltd. All rights reserved.

Glyphosate has limited short-term effects on commensal bacterial community composition in the gut environment due to sufficient aromatic amino acid levels

DEFF Research Database (Denmark)

Nielsen, Lene Nørby; Roager, Henrik Munch; Casas, Mònica Escolà

2017-01-01

in acetic acid produced by the gut bacteria. We conclude that sufficient intestinal levels of aromatic amino acids provided by the diet alleviates the need for bacterial synthesis of aromatic amino acids and thus prevents an antimicrobial effect of glyphosate in vivo. It is however possible...

Amino acid properties conserved in molecular evolution.

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Witold R Rudnicki

Full Text Available That amino acid properties are responsible for the way protein molecules evolve is natural and is also reasonably well supported both by the structure of the genetic code and, to a large extent, by the experimental measures of the amino acid similarity. Nevertheless, there remains a significant gap between observed similarity matrices and their reconstructions from amino acid properties. Therefore, we introduce a simple theoretical model of amino acid similarity matrices, which allows splitting the matrix into two parts - one that depends only on mutabilities of amino acids and another that depends on pairwise similarities between them. Then the new synthetic amino acid properties are derived from the pairwise similarities and used to reconstruct similarity matrices covering a wide range of information entropies. Our model allows us to explain up to 94% of the variability in the BLOSUM family of the amino acids similarity matrices in terms of amino acid properties. The new properties derived from amino acid similarity matrices correlate highly with properties known to be important for molecular evolution such as hydrophobicity, size, shape and charge of amino acids. This result closes the gap in our understanding of the influence of amino acids on evolution at the molecular level. The methods were applied to the single family of similarity matrices used often in general sequence homology searches, but it is general and can be used also for more specific matrices. The new synthetic properties can be used in analyzes of protein sequences in various biological applications.

Effect of x irradiation on the biochemical maturation of rat cerebellum: Metabolism of [14C]glucose and [14C]acetate

International Nuclear Information System (INIS)

Patel, A.J.; Balazs, R.

1975-01-01

The effect was studied of selective x-irradiation of the cerebellum (100 R daily in the first 10 days after birth) on the maturation of glucose metabolism and the development of metabolic compartmentation, in 10-, 16-, and 23-day-old rats by using, respectively, [2- 14 C]glucose and [1- 14 C] acetate (40 μ Ci/100 g body weight each) as precursors. At day 10 significant changes, in comparison with the unirradiated controls, were observed: aspartate and γ-aminobutyrate, respectively, contained 36 percent and 64 percent more and glutamine 42 percent less glucose-carbon combined in amino acids; the glutamine/glutamate specific radioactivity ratio (RSA) was 25 percent less, and the conversion of both glucose and acetate carbons into acid-insoluble constituents was markedly reduced. However, in the postirradiation period both the conversion of glucose carbon into amino acids, and the RSA of glutamine after the administration of [ 14 C]acetate increased in a more or less normal fashion, although certain quantitative differences were noted. It seems, therefore, that the normal progress of biochemical differentiation was only affected to a small degree by the irradiation of the cerebellum, although the treatment interfered severely with cell proliferation. (U.S.)

Foliar application of amino acids modulates aroma components of 'FUJI' apple (malus domestica L.)

International Nuclear Information System (INIS)

Gou, W.; Zhang, L.; Chen, F.; Cui, Z.; Zhao, Y.; Zheng, P.; Tian, L.; Zhang, L.; Zhang, C.

2015-01-01

Volatile flavor compounds play a key role in determining the perception and acceptability as well as enhancing market competitiveness of apple (Malus domestica L.). In our study, we evaluated the effects of foliar-applied four different amino acids, i.e. leucine (Leu), isoleucine (Ile), valine (Val) and alanine (Ala), on aroma components and two key enzymes activities involved in aroma metabolism of Fuji apple. The total amount of aromatic components under Ala treatment was significantly higher than those under other treatments. There was a considerable increase in total aroma content, including hexanal, 2-methyl-butanol, nonanal, (E)-2-hexenal, methyleugenol, ethyl acetate, butanoic acid-pentyl ester, butanoic acid-hexyl ester, butyric acid ethyl ester, acetic acid-2-methyl-butyl ester, treated with spraying amino acids compared with the control. More specifically, hexanal, 2-methyl-butanol, methyleugenol and acetic acid-2-methyl-butyl ester exhibited a greater substantial increase of their contents than those of in other ingredients. However, butanoic acid-2-methyl-2-methyl butyl ester maintained a highest level among all aroma components regardless of different amino acids application. Furthermore, the activities of alcohol dehydrogenase (ADH) and alcohol acyltransferase (AAT) were much higher under Ala treatment than those under other treatments. We concluded that foliar-applied organic nitrogen (N), especially for Ala, can improve aroma metabolism and it could be used in production to enhance fruit quality on a commercial scale. (author)

Oxidative kinetics of amino acids by peroxydisulfate: Effect of dielectric constant

International Nuclear Information System (INIS)

Khalid, Mohammad A. A.

2008-01-01

The kinetics and mechanism of oxidation of alanine, asparagines, cysteine, glutamic acid, lysine, phenylalanine and serine by peroxydisulfate ion have been studied in aqueous acidic (sulfuric acid) medium at the temperature range 60-80C. The rate shows first order dependence on peroxydisulfate concentration and zero order dependence on amino acid concentration. The rate law observed is: -d [S2O82-] /dt = Kobs [S2O82-] [amino acid]0. An autocatalytic effect has been observed in amino acids oxidation due to formation of Schiff's base between the formed aldehyde and parent amino acid. A decrease in the dielectric constant of the medium-adding acetic acid (5-15% v/v) results in a decrease in the rate in all cases studied. Reactions were carried out at different temperature (60-80C) and the thermodynamics parameters have been calculated. The logarithm of the rate constant is linearly interrelated to the square root of the ionic strength. (author)

CO2 sorption by supported amino acid ionic liquids

DEFF Research Database (Denmark)

2014-01-01

The present invention concerns the absorption and desorption behaviour of carbon dioxide (CO2) using ionic liquids derived from amino acids adsorbed on porous carrier materials.......The present invention concerns the absorption and desorption behaviour of carbon dioxide (CO2) using ionic liquids derived from amino acids adsorbed on porous carrier materials....

Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.

Science.gov (United States)

Reyes-Rangel, Gloria; Bandala, Yamir; García-Flores, Fred; Juaristi, Eusebio

2013-09-01

Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a-g to generate the corresponding N-benzoylhydrazine derivatives 4a-g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a-b were subsequently treated with SmI2, and the resulting amino esters 5a-b with LiOH to obtain quaternary α-substituted α-allyl α-amino acids 6a-b, whose absolute configuration was assigned as (S), with fundament on chemical correlation and electronic circular dichroism (ECD) data. © 2013 Wiley Periodicals, Inc.

Genome-wide identification of Saccharomyces cerevisiae genes required for tolerance to acetic acid

Directory of Open Access Journals (Sweden)

Sá-Correia Isabel

2010-10-01

Full Text Available Abstract Background Acetic acid is a byproduct of Saccharomyces cerevisiae alcoholic fermentation. Together with high concentrations of ethanol and other toxic metabolites, acetic acid may contribute to fermentation arrest and reduced ethanol productivity. This weak acid is also a present in lignocellulosic hydrolysates, a highly interesting non-feedstock substrate in industrial biotechnology. Therefore, the better understanding of the molecular mechanisms underlying S. cerevisiae tolerance to acetic acid is essential for the rational selection of optimal fermentation conditions and the engineering of more robust industrial strains to be used in processes in which yeast is explored as cell factory. Results The yeast genes conferring protection against acetic acid were identified in this study at a genome-wide scale, based on the screening of the EUROSCARF haploid mutant collection for susceptibility phenotypes to this weak acid (concentrations in the range 70-110 mM, at pH 4.5. Approximately 650 determinants of tolerance to acetic acid were identified. Clustering of these acetic acid-resistance genes based on their biological function indicated an enrichment of genes involved in transcription, internal pH homeostasis, carbohydrate metabolism, cell wall assembly, biogenesis of mitochondria, ribosome and vacuole, and in the sensing, signalling and uptake of various nutrients in particular iron, potassium, glucose and amino acids. A correlation between increased resistance to acetic acid and the level of potassium in the growth medium was found. The activation of the Snf1p signalling pathway, involved in yeast response to glucose starvation, is demonstrated to occur in response to acetic acid stress but no evidence was obtained supporting the acetic acid-induced inhibition of glucose uptake. Conclusions Approximately 490 of the 650 determinants of tolerance to acetic acid identified in this work are implicated, for the first time, in tolerance to

Purine derivate content and amino acid profile in larval stages of three edible insects.

Science.gov (United States)

Bednářová, Martina; Borkovcová, Marie; Komprda, Tomáš

2014-01-15

Considering their high content of protein, insects are a valuable alternative protein source. However, no evaluation of their purine content has so far been done. High content of purine derivates may lead to the exclusion of such food from the diet of people with specific diseases. The aim of this study was to analyse the content of selected purine derivates and amino acid profile in the three insect species most often used for entomophagy in Europe and compare them with the purine content in egg white and chicken breast. The content of individual purine derivates and their total content were significantly dependent on insect species. The purine content in all three species was significantly higher (P < 0.05) than in egg white, but some values were significantly lower (P < 0.05) than in chicken breast. The total protein content was 548.9 g kg(-1) dry matter (DM) in mealworm (Tenebrio molitor), 551.6 g kg(-1) DM in superworm (Zophobas atratus) and 564.9 g kg(-1) DM in cricket (Gryllus assimilis). Larvae of mealworm and superworm are protein-rich and purine-low meat alternatives. In contrast, cricket nymphs are protein-rich and purine-rich and cannot be recommended for people with hyperuricemia or gout. © 2013 Society of Chemical Industry.

Bioactive Compounds Derived from the Yeast Metabolism of Aromatic Amino Acids during Alcoholic Fermentation

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Albert Mas

2014-01-01

Full Text Available Metabolites resulting from nitrogen metabolism in yeast are currently found in some fermented beverages such as wine and beer. Their study has recently attracted the attention of researchers. Some metabolites derived from aromatic amino acids are bioactive compounds that can behave as hormones or even mimic their role in humans and may also act as regulators in yeast. Although the metabolic pathways for their formation are well known, the physiological significance is still far from being understood. The understanding of this relevance will be a key element in managing the production of these compounds under controlled conditions, to offer fermented food with specific enrichment in these compounds or even to use the yeast as nutritional complements.

Contribution to the study of 14C-acetate as the precursor of aminoacids in detached leaves of coffee (Coffea arabica cv. Mundo Novo)

International Nuclear Information System (INIS)

Brasil, O.G.

1975-01-01

Labelled acetates with 14 C were used as the forerunner of aminoacids in leaves of coffee (Coffea arabica cv Mundo Novo). Leaves with the labelled acetates were incubated and released CO 2 was retained in paper discs with hiamine for further radioactivity detection. Separated proteins furnished 13 amino-acids through acid hidrolysis, all of them were identified by bidimensional filter paper chromatography. Through the obtained results it is possible to conclude that acetates are metabolized by the leafs and are related to the processes of leaf synthesis. It was possible to show that an utilization of acetate for energetical production via Krebs cycle was donne. The obtained conclusions show too that methylic carbon was more incorporated than carboxylic carbon [pt

Synthesis and Biological Evaluation of Novel Jatrorrhizine Derivatives with Amino Groups Linked at the 3-Position as Inhibitors of Acetylcholinesterase

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Xiaofei Jiang

2017-01-01

Full Text Available Jatrorrhizine was considered as one of the active constituents of Coptis chinensis Franch. Herein, jatrorrhizine derivatives with substituted amino groups linked at the 3-position were designed, synthesized, and biologically evaluated as inhibitors of acetylcholinesterase. Jatrorrhizine derivatives inhibited the activity of acetylcholinesterase (AChE to a greater extent than the lead compound jatrorrhizine. All these jatrorrhizine derivatives were proved to be potent inhibitors of acetylcholinesterase (AChE with submicromolar IC50 values, but less sensitive to butyrylcholinesterase (BuChE, which suggests that these jatrorrhizine derivatives are selective for AChE/BuChE. Compound 3g gave the most potent inhibitor activity for AChE (IC50 = 0.301 μM, which is greater than the lead compound jatrorrhizine. All these results demonstrated that these jatrorrhizine derivatives are potential inhibitors for AChE.

Role of acetate in production of an autoinducible Class IIa Bacteriocin in Carnobacterium piscicola A9b

DEFF Research Database (Denmark)

Nilsson, Lilian; Nielsen, Michael Krogsgaard; Ng, Yin

2002-01-01

was to purify the compound and describe factors affecting its production, with particular emphasis on food-relevant factors. Amino acid sequencing showed that the compound is a class IIa bacteriocin with an N-terminal amino acid sequence identical to that of carnobacteriocin B2. The production....... The induction of bacteriocin production showed a dose-dependent relationship at acetate concentrations of up to 10 to 20 mM (depending on the growth medium) and at a concentration of 1.9 x 10(-8) M for the bacteriocin itself; a saturation level of bacteriocin specific activity was reached...

Virtual Combinatorial Library Design, Synthesis and In vitro Anticancer Assessment of -2-Amino-3-Cyanopyridine Derivatives.

Science.gov (United States)

Dev, Sanal; Dhaneshwar, Sunil R; Mathew, Bijo

2018-01-01

For the development of new class of anticancer agents, a series of novel 2-amino-3-cyanopyridine derivatives were designed from virtual screening with Glide program by setting Topoisomerase II as the target. The top ranked ten molecules from the virtual screening were synthesized by microwave assisted technique and investigated for their cytotoxic activity against MCF-7 and A- 549 cell lines by using sulforhodamine B assay method. The most active compound 2-amino-4-(3,5-dibromo-4-hydroxyphenyl)-6-(2,4- dichlorophenyl) nicotinonitrile (CG-5) showed significant cytotoxic profile with (LC50 = 97.1, TGI = 29.9 and GI50 = <0.1 µM) in MCF-7 and (LC50= 93.0, TGI= 50.0 and GI50= <7 µM) in A-549 cell lines. A molecular docking study was performed to explore the binding interaction of CG-5with the active site of Topoisomerase II. It can be concluded that halogen substituent pyridine ring was benefit for cytotoxicity. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Synthesis and Preliminary Biological Evaluation of 1,3,5-Triazine Amino Acid Derivatives to Study Their MAO Inhibitors

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Sherine N. Khattab

2015-09-01

Full Text Available Three series of 4,6-dimethoxy-, 4,6-dipiperidino- and 4,6-dimorpholino-1,3,5-triazin-2-yl amino acid derivatives were synthesized and characterized. A preliminary study for their monoamine oxidase inhibitory activity showed that compounds 7, 18, and 25 had MAO-A inhibition activity comparable to that of the standard clorgyline, with apparently more selective inhibitory activity toward MAO-A than MAO-B and no significant acute toxicity.

Amino acid sequence of bovine muzzle epithelial desmocollin derived from cloned cDNA: a novel subtype of desmosomal cadherins.

Science.gov (United States)

Koch, P J; Goldschmidt, M D; Walsh, M J; Zimbelmann, R; Schmelz, M; Franke, W W

1991-05-01

Desmosomes are cell-type-specific intercellular junctions found in epithelium, myocardium and certain other tissues. They consist of assemblies of molecules involved in the adhesion of specific cell types and in the anchorage of cell-type-specific cytoskeletal elements, the intermediate-size filaments, to the plasma membrane. To explore the individual desmosomal components and their functions we have isolated DNA clones encoding the desmosomal glycoprotein, desmocollin, using antibodies and a cDNA expression library from bovine muzzle epithelium. The cDNA-deduced amino-acid sequence of desmocollin (presently we cannot decide to which of the two desmocollins, DC I or DC II, this clone relates) defines a polypeptide with a calculated molecular weight of 85,000, with a single candidate sequence of 24 amino acids sufficiently long for a transmembrane arrangement, and an extracellular aminoterminal portion of 561 amino acid residues, compared to a cytoplasmic part of only 176 amino acids. Amino acid sequence comparisons have revealed that desmocollin is highly homologous to members of the cadherin family of cell adhesion molecules, including the previously sequenced desmoglein, another desmosome-specific cadherin. Using riboprobes derived from cDNAs for Northern-blot analyses, we have identified an mRNA of approximately 6 kb in stratified epithelia such as muzzle epithelium and tongue mucosa but not in two epithelial cell culture lines containing desmosomes and desmoplakins. The difference may indicate drastic differences in mRNA concentration or the existence of cell-type-specific desmocollin subforms. The molecular topology of desmocollin(s) is discussed in relation to possible functions of the individual molecular domains.

Global insights into acetic acid resistance mechanisms and genetic stability of Acetobacter pasteurianus strains by comparative genomics

Science.gov (United States)

Wang, Bin; Shao, Yanchun; Chen, Tao; Chen, Wanping; Chen, Fusheng

2015-12-01

Acetobacter pasteurianus (Ap) CICC 20001 and CGMCC 1.41 are two acetic acid bacteria strains that, because of their strong abilities to produce and tolerate high concentrations of acetic acid, have been widely used to brew vinegar in China. To globally understand the fermentation characteristics, acid-tolerant mechanisms and genetic stabilities, their genomes were sequenced. Genomic comparisons with 9 other sequenced Ap strains revealed that their chromosomes were evolutionarily conserved, whereas the plasmids were unique compared with other Ap strains. Analysis of the acid-tolerant metabolic pathway at the genomic level indicated that the metabolism of some amino acids and the known mechanisms of acetic acid tolerance, might collaboratively contribute to acetic acid resistance in Ap strains. The balance of instability factors and stability factors in the genomes of Ap CICC 20001 and CGMCC 1.41 strains might be the basis for their genetic stability, consistent with their stable industrial performances. These observations provide important insights into the acid resistance mechanism and the genetic stability of Ap strains and lay a foundation for future genetic manipulation and engineering of these two strains.

Synthesis of formazans from Mannich base of 5-(4-chlorophenyl amino-2-mercapto-1,3,4-thiadiazole as antimicrobial agents

Directory of Open Access Journals (Sweden)

Pramilla Sah

2014-04-01

Full Text Available 5-(4-Chlorophenyl amino-2-mercapto-1,3,4-thiadiazole (I was refluxed with formaldehyde and ammonium chloride in ethanol yielding the Mannich base 5-(4-chloro phenyl amino-3-aminomethyl-2-mercapto-1,3,4-thiadiazole (II. Esterification with 4-chloro-(2,6-dinitro phenoxy-ethyl acetate (III under anhydrous conditions gave the intermediate (IV. Subsequent hydrazinolysis with hydrazine hydrate gave the corresponding hydrazide 3-amino methyl-5-(4-chloro phenyl amino-2-mercapto-4′-(2′,6′-dinitro phenoxy-acetyl hydrazide (V. The hydrazide was converted into the Schiff bases (VIa–b by reacting with 2-chlorobenzaldehyde and 3-methoxy-4-hydroxy benzaldehyde in presence of methanol containing 2–3 drops of acetic acid. Diazotisation with aromatic amines, sulphanilic acid and sulphur drugs gave the formazans (VIIa–g respectively. Chemical structures have been established by elemental analysis and the spectral techniques of FTIR, 1H NMR and mass. Antimicrobial activity (in vitro was evaluated against the two pathogenic bacterial strains. Escherichia coli and Salmonella typhi, three fungal strains Aspergillus niger, Penicillium species and Candida albicans. The compounds have shown moderate activity.

Cytotoxic effect of betulinic acid and betulinic acid acetate isolated ...

African Journals Online (AJOL)

GREGORY

2010-09-20

Sep 20, 2010 ... Betulinic acid acetate (BAAC) was most effective than other betulinic acid derivatives. It had most ... blastoma (Schmidt et al., 1997), malignant brain tumor .... 96 well plate and incubated in 37oC, 5% CO2 and 90% humidity.

Uncovering the Design Principle of Amino Acid-Derived Photoluminescent Biodots with Tailor-Made Structure-Properties and Applications for Cellular Bioimaging.

Science.gov (United States)

Xu, Hesheng Victor; Zheng, Xin Ting; Zhao, Yanli; Tan, Yen Nee

2018-06-01

Natural amino acids possess side chains with different functional groups (R groups), which make them excellent precursors for programmable synthesis of biomolecule-derived nanodots (biodots) with desired properties. Herein, we report the first systematic study to uncover the material design rules of biodot synthesis from 20 natural α-amino acids via a green hydrothermal approach. The as-synthesized amino acid biodots (AA dots) are comprehensively characterized to establish a structure-property relationship between the amino acid precursors and the corresponding photoluminescent properties of AA dots. It was found that the amino acids with reactive R groups, including amine, hydroxyl, and carboxyl functional groups form unique C-O-C/C-OH and N-H bonds in the AA dots which stabilize the surface defects, giving rise to brightly luminescent AA dots. Furthermore, the AA dots were found to be amorphous and the length of the R group was observed to affect the final morphology (e.g., disclike nanostructure, nanowire, or nanomesh) of the AA dots, which in turn influence their photoluminescent properties. It is noteworthy to highlight that the hydroxyl-containing amino acids, that is, Ser and Thr, form the brightest AA dots with a quantum yield of 30.44% and 23.07%, respectively, and possess high photostability with negligible photobleaching upon continuous UV exposure for 3 h. Intriguingly, by selective mixing of Ser or Thr with another amino acid precursor, the resulting mixed AA dots could inherit unique properties such as improved photostability and significant red shift in their emission wavelength, producing enhanced green and red fluorescent intensity. Moreover, our cellular studies demonstrate that the as-synthesized AA dots display outstanding biocompatibility and excellent intracellular uptake, which are highly desirable for imaging applications. We envision that the material design rules discovered in this study will be broadly applicable for the rational

Synthesis of .alpha.-Amino Acids via Asymmetric Phase Transfer-Catalyzed Alkylation of Achiral Niclkel(II) Complexes of Glycine-Derived Schiff bases

Czech Academy of Sciences Publication Activity Database

Belokon, Y. N.; Bespalova, N. B.; Churkina, T. D.; Císařová, I.; Ezernitskaya, M. G.; Harutyunyan, S. R.; Hrdina, R.; Kagan, H. B.; Kočovský, P.; Kochetkov, K. A.; Larionov, O. G.; Lysenko, K. A.; North, M.; Polášek, Miroslav; Peregudov, A. S.; Prisyazhnyuk, V. V.; Vyskočil, Š.

2003-01-01

Roč. 125, - (2003), s. 12860-12870 ISSN 0002-7863 R&D Projects: GA ČR GP203/01/D051 Institutional research plan: CEZ:AV0Z4040901 Keywords : .alpha.amino acids * achiral nickel(II) * glycine-derived schiff bases Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 6.516, year: 2003

Partial molar volumes of proteins: amino acid side-chain contributions derived from the partial molar volumes of some tripeptides over the temperature range 10-90 degrees C.

Science.gov (United States)

Häckel, M; Hinz, H J; Hedwig, G R

1999-11-15

The partial molar volumes of tripeptides of sequence glycyl-X-glycine, where X is one of the amino acids alanine, leucine, threonine, glutamine, phenylalanine, histidine, cysteine, proline, glutamic acid, and arginine, have been determined in aqueous solution over the temperature range 10-90 degrees C using differential scanning densitometry . These data, together with those reported previously, have been used to derive the partial molar volumes of the side-chains of all 20 amino acids. The side-chain volumes are critically compared with literature values derived using partial molar volumes for alternative model compounds. The new amino acid side-chain volumes, along with that for the backbone glycyl group, were used to calculate the partial specific volumes of several proteins in aqueous solution. The results obtained are compared with those observed experimentally. The new side-chain volumes have also been used to re-determine residue volume changes upon protein folding.

Synthesis and chemical characterization of the novel agronomically relevant pentadentate chelate 2-(2-((2-hydroxybenzyl)amino)ethylamino)-2-(2-hydroxyphenyl)acetic acid (DCHA).

Science.gov (United States)

López-Rayo, Sandra; Hernández, Diana; Lucena, Juan J; Escudero, Rosa; Gómez-Gallego, Mar; Sierra, Miguel A

2010-07-14

Iron chelates analogous to o,o-EDDHA/Fe(3+) are the fertilizers chosen to treat iron chlorosis in plants growing on calcareous soil. The isomer o,p-EDDHA/Fe(3+) presents less stability but faster assimilation by the plant than o,o-EDDHA/Fe(3+), because only five coordinating groups are able to complex Fe(3+). The new chelating agent 2-(2-((2-hydroxybenzyl)amino)ethylamino)-2-(2-hydroxyphenyl)acetic acid (DCHA) has been synthesized to obtain an iron fertilizer with intermediate stability between o,o-EDDHA/Fe(3+) and o,p-EDDHA/Fe(3+) and with fast assimilation. Its synthesis has been done starting from phenol, N-acetylethylendiamine, glyoxylic acid, and NaOH in a three-step sequence. The purity of the DCHA chelating agent, its protonation, and Ca(2+), Mg(2+), Fe(3+), and Cu(2+) stability constants, together with its ability to maintain iron in solution in different agronomic conditions, have been determined. The results indicate that the chelate DCHA/Fe(3+) has intermediate stability between those of o,o-EDDHA/Fe(3+) and o,p-EDDHA/Fe(3+) complexes and that it is capable of maintaining the Fe(3+) in agronomic conditions. This new chelating agent may be effective in correcting iron chlorosis in plants.

Furan- and Thiophene-2-Carbonyl Amino Acid Derivatives Activate Hypoxia-Inducible Factor via Inhibition of Factor Inhibiting Hypoxia-Inducible Factor-1

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Shin-ichi Kawaguchi

2018-04-01

Full Text Available Induction of a series of anti-hypoxic proteins protects cells during exposure to hypoxic conditions. Hypoxia-inducible factor-α (HIF-α is a major transcription factor that orchestrates this protective effect. To activate HIF exogenously, without exposing cells to hypoxic conditions, many small-molecule inhibitors targeting prolyl hydroxylase domain-containing protein have been developed. In addition, suppression of factor inhibiting HIF-1 (FIH-1 has also been shown to have the potential to activate HIF-α. However, few small-molecule inhibitors of FIH-1 have been developed. In this study, we synthesized a series of furan- and thiophene-2-carbonyl amino acid derivatives having the potential to inhibit FIH-1. The inhibitory activities of these compounds were evaluated in SK-N-BE(2c cells by measuring HIF response element (HRE promoter activity. Several furan- and thiophene-2-carbonyl amino acid derivatives inhibited FIH-1 based on correlations among the docking score of the FIH-1 active site, the chemical structure of the compounds, and biological HIF-α/HRE transcriptional activity.

Extraction of left ventricular myocardial mass from dynamic 11C-acetate PET

DEFF Research Database (Denmark)

Harms, Hans; Tolbod, Lars Poulsen; Hansson, Nils Henrik

Background: Dynamic 11C-acetate PET is used to quantify oxygen metabolism, which is used to calculate left ventricular (LV) myocardial efficiency, an early marker of heart failure. This requires estimation of LV myocardial mass and is typically derived from a separate cardiovascular magnetic...... resonance (CMR) scan. The aim of this study was to explore the feasibility of estimating myocardial mass directly from a dynamic 11C-acetate PET scan. Methods: 21 subjects underwent a 27-min 11C-acetate PET scan on a Siemens Biograph TruePoint 64 PET/CT scanner. In addition, 10 subjects underwent a dynamic...... 11C-acetate 27-min PET scan on a GE Discovery ST PET/CT scanner. Parametric images of uptake rate K1 and both arterial (VA) and venous (VV) spillover fractions were generated using a basis function implementation of the standard single tissue compartment model using non-gated dynamic data. The LV...

Evolution of the biosynthesis of the branched-chain amino acids

Science.gov (United States)

Keefe, Anthony D.; Lazcano, Antonio; Miller, Stanley L.

1995-01-01

The origins of the biosynthetic pathways for the branched-chain amino acids cannot be understood in terms of the backwards development of the present acetolactate pathway because it contains unstable intermediates. We propose that the first biosynthesis of the branched-chain amino acids was by the reductive carboxylation of short branched chain fatty acids giving keto acids which were then transaminated. Similar reaction sequences mediated by nonspecific enzymes would produce serine and threomine from the abundant prebiotic compounds glycolic and lactic acids. The aromatic amino acids may also have first been synthesized in this way, e.g. tryptophan from indole acetic acid. The next step would have been the biosynthesis of leucine from alpha-ketoisovalerc acid. The acetolactate pathway developed subsequently. The first version of the Krebs cycle, which was used for amino acid biosynthesis, would have been assembled by making use fo the reductive carboxylation and leucine biosynthesis enzymes, and completed with the development of a single new enzyme, succinate dehydrogenase. This evolutionary scheme suggests that there may be limitations to inferring the origins of metabolism by a simple back extrapolation of current pathways.

Carbobenzoxy amino acids: Structural requirements for cholecystokinin receptor antagonist activity

International Nuclear Information System (INIS)

Maton, P.N.; Sutliff, V.E.; Jensen, R.T.; Gardner, J.D.

1985-01-01

The authors used dispersed acini prepared from guinea pig pancreas to examine 28 carbobenzoxy (CBZ) amino acids for their abilities to function as cholecystokinin receptor antagonists. All amino acid derivatives tested, except for CBZ-alanine, CBZ-glycine, and N alpha-CBZ- lysine, were able to inhibit the stimulation of amylase secretion caused by the C-terminal octapeptide of cholecystokinin. In general, there was a good correlation between the ability of a carbobenzoxy amino acid to inhibit stimulated amylase secretion and the ability of the amino acid derivative to inhibit binding of 125 I-cholecystokinin. The inhibition of cholecystokinin-stimulated amylase secretion was competitive, fully reversible, and specific for those secretagogues that interact with the cholecystokinin receptor. The potencies with which the various carbobenzoxy amino acids inhibited the action of cholecystokinin varied 100-fold and CBZ-cystine was the most potent cholecystokinin receptor antagonist. This variation in potency was primarily but not exclusively a function of the hydrophobicity of the amino acid side chain

Drug-loaded Cellulose Acetate and Cellulose Acetate Butyrate Films ...

African Journals Online (AJOL)

The purpose of this research work was to evaluate the contribution of formulation variables on release properties of matrix type ocular films containing chloramphenicol as a model drug. This study investigated the use of cellulose acetate and cellulose acetate butyrate as film-forming agents in development of ocular films.

Alkylation or Silylation for Analysis of Amino and Non-Amino Organic Acids by GC-MS?

Directory of Open Access Journals (Sweden)

Silas G. Villas-Bôas

2011-01-01

Full Text Available Gas chromatography–mass spectrometry (GC-MS is a widely used analytical technique in metabolomics. GC provides the highest resolution of any standard chromatographic separation method, and with modern instrumentation, retention times are very consistent between analyses. Electron impact ionization and fragmentation is generally reproducible between instruments and extensive libraries of spectra are available that enhance the identification of analytes. The major limitation is the restriction to volatile analytes, and hence the requirement to convert many metabolites to volatile derivatives through chemical derivatization. Here we compared the analytical performance of two derivatization techniques, silylation (TMS and alkylation (MCF, used for the analysis of amino and non-amino organic acids as well as nucleotides in microbial-derived samples. The widely used TMS derivatization method showed poorer reproducibility and instability during chromatographic runs while the MCF derivatives presented better analytical performance. Therefore, alkylation (MCF derivatization seems to be preferable for the analysis of polyfunctional amines, nucleotides and organic acids in microbial metabolomics studies.

Synthesis of some pyridine and pyrimidine derivatives via Michael-Addition

International Nuclear Information System (INIS)

El-Baih, Fatma E.M.; Al-Rasheed, Hessa H.; Al-Hazimi, Hassan M.

2006-01-01

Synthesis of pyridine and pyrimidine analogues 4 and 6-9 were achieved by Michael-addition of compounds containing either active methylene groups like, malononitrile , ethyl cyanoacetate and 1-tetralone or compounds containing active hydrogen atoms like, guanidine in the presence of an oxidizing agent and thiourea to 2-arylmethylidine-1-tetralone and 2-arylmethylidine-6-methoxy-1-tetralone (2) (enones). Addition of malononitrile in piperidine at room temperature to 2-amino-3-cyno-naphtho [1, 2-malonoitrile in sodium alkoxide or sodium hydroxide to 2 gave 4. Cyclization of 3a with acetic anhydride in the presence of conc. H2sO4 gave the naphtha-pyrano[2, 3-d]pyrimidin-8-one (5). Condensation of the pyrimidine thione derivatives 9 with chloroacetic acid gave the 3-oxobenzo[h]thiazoladino[2, 3-b]quinazoline derivatives (10), which were reacted through their active methylene groups with aromatic aldehydes to give the arylidine derivatives 11. These compounds were also prepared in one step by reacting 9 with chloroacetic acid and aromatic aldehydes. Condensation of 9 with 3-bromopropanoic acid gave 4-oxo-benzo[h]1, 3-thiazino[2, 3-b]quinazoline derivatives (12). The structures of the prepared compounds were mainly confirmed on the basis of spectroscopic methods. (author)

Quantum mechanics and molecular dynamics simulations of complexation of alkaline-earth and lanthanide cations by poly-amino-carboxylate ligands; Simulations par mecanique quantique et dynamique moleculaire de la complexation de cations alcalino-terreux et lanthanides par des ligands polyaminocarboxylates

Energy Technology Data Exchange (ETDEWEB)

Durand, S

1999-07-01

Molecular dynamics (MD) simulations on lanthanide(III) and alkaline-earth(II) complexes with poly-amino-carboxylates (ethylene-diamino-tetra-acetate EDTA{sup 4-}, ethylene-diamino-tri-acetate-acetic acid EDTA(H){sup 3-}, tetra-aza-cyclo-dodecane-tetra-acetate DOTA{sup 4-}, methylene-imidine-acetate MIDA{sup 2-}) are reported. First, a consistent set of Lennard-Jones parameters for La{sup 3+}, Eu{sup 3+} and Lu{sup 3+} cations has been derived from free energy calculations in aqueous solution. Observed differences in hydration free energies, coordination distances and hydration numbers are reproduced. Then, the solution structures of 1:1 complexes of alkaline-earth and/or lanthanide cations with EDTA{sup 4-}, EDTA(H){sup 3-}, DOTA{sup 4-} and 1:2 complexes of lanthanide cations with MIDA{sup 2-} were studied by MD in water. In addition, free energy calculations were performed to study, for each ligand, the relative thermodynamic stabilities of complexes with Ca{sup 2+} vs Sr{sup 2+} and vs Ba{sup 2+} on the one hand, and with La{sup 3+} vs Eu{sup 3+} and vs Lu{sup 3+} on the other hand. Model does not take into account explicitly polarization and charge transfer. However, the results qualitatively agree with experimental complexation data (structure and selectivities). (author)

Comparative study on the composition of free amino acids and derivatives in the two botanical origins of an edible Chinese herb "Xiebai", i.e., Allium chinense G. Don and Allium macrostemon Bunge species.

Science.gov (United States)

He, Quan; Huang, Shaohui; Wu, Yuehong; Zhang, Wenqi; Wang, Fanchao; Cao, Jiawei; Sheng, Qing; Liang, Zongsuo; Liu, Lili; Ou, Wen-Bin

2018-04-01

Xiebai is an edible Chinese herb with various health and therapeutic benefits. To evaluate its nutritional and health values, the free amino acids and derivatives of its two botanical origins (i.e., Allium chinense G. Don and Allium macrostemon Bunge) were isolated using a solvent extraction method and analyzed using automatic amino acid analysis and ultra-performance liquid chromatography-quadrupole-time of flight (UPLC-Q-TOF) mass spectrometry. Our data show that both plants contain abundant free amino acids, and the amount of total free amino acids in A. chinense G. Don is higher than that in A. macrostemon Bunge. The free amino acid compositions in the two plants are qualitatively similar, including nineteen proteinogenic and four non-proteinogenic amino acids. The identified proteinogenic amino acids include eight essential amino acids and five semi-essential amino acids. The sum of essential and semi-essential amino acids accounts for 64.9% and 69.7% of the total free amino acids of the two plants, respectively. The principal amino acids of both plants, from highest concentration to lowest concentration, are arginine, glutamine, glutamic acid, asparagine and serine. A. chinense G. Don is also rich in citrulline and lysine. In addition, two amino acid derivatives were identified from the two plants, i.e., the proline analog N‑methyl‑proline and the dipeptide H-Glu-Tyr-OH. For the first time, the presence of N‑methyl‑proline in the plants of the Allium genus and the presence of H-Glu-Tyr-OH in unprocessed food sources are reported. The influences of the identified substances on the flavor, nutrition and health values of Xiebai are discussed. Copyright © 2018 Elsevier Ltd. All rights reserved.

Agrobacterium tumefaciens responses to plant-derived signaling molecules

Science.gov (United States)

Subramoni, Sujatha; Nathoo, Naeem; Klimov, Eugene; Yuan, Ze-Chun

2014-01-01

As a special phytopathogen, Agrobacterium tumefaciens infects a wide range of plant hosts and causes plant tumors also known as crown galls. The complexity of Agrobacterium–plant interaction has been studied for several decades. Agrobacterium pathogenicity is largely attributed to its evolved capabilities of precise recognition and response to plant-derived chemical signals. Agrobacterium perceives plant-derived signals to activate its virulence genes, which are responsible for transferring and integrating its Transferred DNA (T-DNA) from its Tumor-inducing (Ti) plasmid into the plant nucleus. The expression of T-DNA in plant hosts leads to the production of a large amount of indole-3-acetic acid (IAA), cytokinin (CK), and opines. IAA and CK stimulate plant growth, resulting in tumor formation. Agrobacterium utilizes opines as nutrient sources as well as signals in order to activate its quorum sensing (QS) to further promote virulence and opine metabolism. Intriguingly, Agrobacterium also recognizes plant-derived signals including γ-amino butyric acid and salicylic acid (SA) to activate quorum quenching that reduces the level of QS signals, thereby avoiding the elicitation of plant defense and preserving energy. In addition, Agrobacterium hijacks plant-derived signals including SA, IAA, and ethylene to down-regulate its virulence genes located on the Ti plasmid. Moreover, certain metabolites from corn (Zea mays) also inhibit the expression of Agrobacterium virulence genes. Here we outline the responses of Agrobacterium to major plant-derived signals that impact Agrobacterium–plant interactions. PMID:25071805

Agrobacterium tumefaciens responses to plant-derived signaling molecules

Directory of Open Access Journals (Sweden)

Sujatha eSubramoni

2014-07-01

Full Text Available As a special phytopathogen, Agrobacterium tumefaciens infects a wide range of plant hosts and causes plant tumors also known as crown galls. The complexity of Agrobacterium-plant interaction has been studied for several decades. Agrobacterium pathogenicity is largely attributed to its evolved capabilities of precise recognition and response to plant-derived chemical signals. Agrobacterium perceives plant-derived signals to activate its virulence genes, which are responsible for transferring and integrating its T-DNA (Transferred DNA from its Tumour-inducing (Ti plasmid into the plant nucleus. The expression of T-DNA in plant hosts leads to the production of a large amount of indole-3-acetic acid (IAA, cytokinin (CK and opines. IAA and CK stimulate plant growth, resulting in tumor formation. Agrobacterium utilizes opines as nutrient sources as well as signals in order to activate its quorum sensing (QS to further promote virulence and opine metabolism. Intriguingly, Agrobacterium also recognizes plant-derived signals including -amino butyric acid (GABA and salicylic acid (SA to activate quorum quenching that reduces the level of QS signals, thereby avoiding the elicitation of plant defense and preserving energy. In addition, Agrobacterium hijacks plant-derived signals including SA, IAA, and ethylene (ET to down-regulate its virulence genes located on the Ti plasmid. Moreover, certain metabolites from corn (Zea mays also inhibit the expression of Agrobacterium virulence genes. Here we outline the responses of Agrobacterium to major plant-derived signals that impact Agrobacterium-plant interactions.

Synthesis and dynamic NMR study of ketenimines derived from tert-butyl isocyanide, alkyl 2-arylamino-2-oxo-acetates, and dialkyl acetylenedicarboxylates.

Science.gov (United States)

Yavari, Issa; Nasiri, Farough; Djahaniani, Horieh

2004-01-01

The adduct produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped by alkyl 2-arylamino-2-oxo-acetates. When the aryl group is 2-methyl-6-nitrophenyl or 2,6-di-isopropylphenyl, the product exists as two stable rotamers at room temperature as a result of restricted rotation around the Ar-N single bond. When the aryl group is 1-naphthyl or 8-quinolinyl, dynamic NMR effects are observed in the 1H NMR spectra. The calculated free-energy of activation for interconversion of the rotational isomers in 1-naphthyl and 8-quinolinyl derivatives amounts to about 99+/-2 and 68.5+/-2 kJ mol(-1), respectively.

A case of anaphylactoid reaction to acetate in acetate-containing bicarbonate dialysate.

Science.gov (United States)

Misaki, Taro; Suzuki, Yumiko; Naito, Yoshitaka; Shiooka, Tempei; Isozaki, Taisuke

2015-05-01

A 35-year-old man with end-stage kidney disease due to chronic glomerulonephritis was admitted to our hospital to start maintenance hemodialysis (HD). One hour after starting the first session of HD, he experienced general pruritus, urticaria, and dyspnea. Signs and symptoms were resolved by discontinuing HD and administrating an antihistamine drug; HD-associated anaphylactoid reactions were therefore suspected. Over the next few HD sessions, we changed the dialysis membrane, anticoagulant, HD circuit and needle, in that order, but general pruritus and urticaria again appeared within 3 h after starting each session of HD. Finally, when we changed the dialysate from acetate-containing bicarbonate dialysate to acetate-free bicarbonate dialysate, urticaria was clearly less than that seen in previous HD sessions, and subsided after discontinuation of HD. Subsequently, 20 mg of oral prednisolone (PSL) was administered 1 h before starting HD, and the patient did not experience general pruritus, urticaria, or dyspnea after starting the session. When administered acetate-containing bicarbonate dialysate after oral PSL pretreatment, the patient again experienced general pruritus, urticaria and dyspnea. Few reports have been published on the occurrence of anaphylactoid reactions during HD using acetate dialysate. We report a rare case of anaphylactoid reactions with acetate in acetate-containing bicarbonate dialysate that were reduced with the use of acetate-free bicarbonate dialysate and oral PSL pretreatment.

PCI-GC-MS-MS approach for identification of non-amino organic acid and amino acid profiles.

Science.gov (United States)

Luan, Hemi; Yang, Lin; Ji, Fenfen; Cai, Zongwei

2017-03-15

Alkyl chloroformate have been wildly used for the fast derivatization of metabolites with amino and/or carboxyl groups, coupling of powerful separation and detection systems, such as GC-MS, which allows the comprehensive analysis of non-amino organic acids and amino acids. The reagents involving n-alkyl chloroformate and n-alcohol are generally employed for providing symmetric labeling terminal alkyl chain with the same length. Here, we developed an asymmetric labeling strategy and positive chemical ionization gas chromatography-tandem mass spectrometry (PCI-GC-MS-MS) approach for determination of non-amino organic acids and amino acids, as well as the short chain fatty acids. Carboxylic and amino groups could be selectively labelled by propyl and ethyl groups, respectively. The specific neutral loss of C 3 H 8 O (60Da), C 3 H 5 O 2 (74Da) and C 4 H 8 O 2 (88Da) were useful in the selective identification for qualitative analysis of organic acids and amino acid derivatives. PCI-GC-MS-MS using multiple reaction monitoring (MRM) was applied for semi-quantification of typical non-amino organic acids and amino acids. This method exhibited a wide range of linear range, good regression coefficient (R 2 ) and repeatability. The relative standard deviation (RSD) of targeted metabolites showed excellent intra- and inter-day precision (chloroformate derivatization. Copyright © 2016 Elsevier B.V. All rights reserved.

Enantioseparation of dansyl amino acids by HPLC on a monolithic column dynamically coated with a vancomycin derivative.

Science.gov (United States)

Pittler, Elfriede; Schmid, Martin G

2010-11-01

In this work a chiral stationary phase was prepared by dynamically coating a monolithic reversed-phase HPLC column with a vancomycin-derivative as chiral selector. A hydrophobic alkyl-chain was attached to the vancomycin molecule, providing the immobilization of the chiral selector on the reversed-phase material. Dansyl amino acids were chosen as model analytes for testing the separation power of the dynamically coated phase. All investigated compounds were separated into their enantiomers. Compared with a conventionally packed vancomycin-CSP, a reversal of the enantiomer elution order was obtained. Copyright © 2010 John Wiley & Sons, Ltd.

Copper(II Complexes with Ligands Derived from 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Synthesis and Biological Activity

Directory of Open Access Journals (Sweden)

Raluca Cernat

2006-11-01

Full Text Available The synthesis of Cu(II complexes derived from Schiff base ligands obtainedby the condensation of 2-hydroxybenzaldehyde or terephtalic aldehyde with 4-amino-antipyrine (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one is presented. The newlyprepared compounds were characterized by 1H-NMR, UV-VIS, IR and ESRspectroscopy. The determination of the antimicrobial activity of the ligands and of thecomplexes was carried out on samples of Escherichia coli, Klebsiella pneumoniae,Acinetobacter boumanii, Pseudomonas aeruginosa, Staphylococcus aureus and Candidasp. The qualitative and quantitative antimicrobial activity test results proved that all theprepared complexes are very active, especially against samples of Ps. aeruginosa, A.Boumanii, E. coli and S. aureus.

Fermentable soluble fibres spare amino acids in healthy dogs fed a low-protein diet.

Science.gov (United States)

Wambacq, Wendy; Rybachuk, Galena; Jeusette, Isabelle; Rochus, Kristel; Wuyts, Brigitte; Fievez, Veerle; Nguyen, Patrick; Hesta, Myriam

2016-06-28

Research in cats has shown that increased fermentation-derived propionic acid and its metabolites can be used as alternative substrates for gluconeogenesis, thus sparing amino acids for other purposes. This amino acid sparing effect could be of particular interest in patients with kidney or liver disease, where this could reduce the kidneys'/liver's burden of N-waste removal. Since dogs are known to have a different metabolism than the obligatory carnivorous cat, the main objective of this study was to assess the possibility of altering amino acid metabolism through intestinal fermentation in healthy dogs. This was studied by supplementing a low-protein diet with fermentable fibres, hereby providing an initial model for future studies in dogs suffering from renal/liver disease. Eight healthy dogs were randomly assigned to one of two treatment groups: sugar beet pulp and guar gum mix (SF: soluble fibre, estimated to mainly stimulate propionic acid production) or cellulose (IF: insoluble fibre). Treatments were incorporated into a low-protein (17 %) extruded dry diet in amounts to obtain similar total dietary fibre (TDF) contents for both diets (9.4 % and 8.2 % for the SF and IF diet, respectively) and were tested in a 4-week crossover feeding trial. Apparent faecal nitrogen digestibility and post-prandial fermentation metabolites in faeces and plasma were evaluated. Dogs fed the SF diet showed significantly higher faecal excretion of acetic and propionic acid, resulting in a higher total SCFA excretion compared to IF. SF affected the three to six-hour postprandial plasma acylcarnitine profile by significantly increasing AUC of acetyl-, propionyl-, butyryl- + isobutyryl-, 3-OH-butyryl-, 3-OH-isovaleryl- and malonyl-L-carnitine. Moreover, the amino acid plasma profile at that time was modified as leucine + isoleucine concentrations were significantly increased by SF, and a similar trend for phenylalanine and tyrosine's AUC was found. These results indicate

Additive effects of acetic acid upon hydrothermal reaction of amylopectin

International Nuclear Information System (INIS)

Sugano, Motoyuki; Katoh, Harumi; Komatsu, Akihiro; Kobayashi, Hiroshi; Okado, Kohta; Kakuta, Yusuke; Hirano, Katsumi

2012-01-01

It is well known that over 0.8 kg kg −1 of starch is consisted of amylopectin (AP). In this study, production of glucose for raw material of ethanol by hydrothermal reaction of AP as one of the model compound of food is discussed. Further, additive effects of acetic acid upon hydrothermal reactions of AP are also investigated. During hydrothermal reaction of AP, production of glucose occurred above 453 K, and the glucose yield increased to 0.48 kg kg −1 at 473 K. Upon hydrothermal reaction of AP at 473 K, prolongation of the holding time was not effective for the increase of the glucose yield. Upon hydrothermal reaction of AP at 473 K for 0 s, the glucose yield increased significantly by addition between 0.26 mol L −1 and 0.52 mol L −1 of acetic acid. However, the glucose yield decreased and the yield of the other constituents increased with the increases of concentration of acetic acid from 0.65 mol L −1 to 3.33 mol L −1 . It was considered that hydrolysis of AP to yield glucose was enhanced due to the increase of the amount of proton derived from acetic acid during hydrothermal reaction with 0.52 mol L −1 of acetic acid. -- Highlights: ► Glucose production by hydrothermal reaction of amylopectin (AP) at 473 K. ► Glucose yield increased to 0.48 kg kg -1 at 473 K. ► Prolongation of holding time was not effective for glucose yield. ► Glucose yield increased significantly by acetic acid (0.26–0.52 mol L-1) addition. ► Hydrolysis of AP to glucose was enhanced due to increase of proton from acetic acid.

Cytotoxic effect of betulinic acid and betulinic acid acetate isolated ...

African Journals Online (AJOL)

Cytotoxic effect of betulinic acid and betulinic acid acetate isolated from Melaleuca cajuput on human myeloid leukemia (HL-60) cell line. ... The cytotoxic effect of betulinic acid (BA), isolated from Melaleuca cajuput a Malaysian plant and its four synthetic derivatives were tested for their cytotoxicity in various cell line or ...

Metformin inhibits Branched Chain Amino Acid (BCAA) derived ketoacidosis and promotes metabolic homeostasis in MSUD.

Science.gov (United States)

S Sonnet, Davis; N O'Leary, Monique; A Gutierrez, Mark; M Nguyen, Steven; Mateen, Samiha; Hsu, Yuehmei; P Mitchell, Kylie; J Lopez, Antonio; Vockley, Jerry; K Kennedy, Brian; Ramanathan, Arvind

2016-07-04

Maple Syrup Urine Disease (MSUD) is an inherited disorder caused by the dysfunction in the branched chain keto-acid dehydrogenase (BCKDH) enzyme. This leads to buildup of branched-chain keto-acids (BCKA) and branched-chain amino acids (BCAA) in body fluids (e.g. keto-isocaproic acid from the BCAA leucine), leading to numerous clinical features including a less understood skeletal muscle dysfunction in patients. KIC is an inhibitor of mitochondrial function at disease relevant concentrations. A murine model of intermediate MSUD (iMSUD) shows significant skeletal muscle dysfunction as by judged decreased muscle fiber diameter. MSUD is an orphan disease with a need for novel drug interventions. Here using a 96-well plate (liquid chromatography- mass spectrometry (LC-MS) based drug-screening platform we show that Metformin, a widely used anti-diabetic drug, reduces levels of KIC in patient-derived fibroblasts by 20-50%. This Metformin-mediated effect was conserved in vivo; Metformin-treatment significantly reduced levels of KIC in the muscle (by 69%) and serum (by 56%) isolated from iMSUD mice, and restored levels of mitochondrial metabolites (e.g. AMP and other TCA). The drug also decreased the expression of mitochondrial branched chain amino transferase (BCAT) which produces KIC in skeletal muscle. This suggests that Metformin can restore skeletal muscle homeostasis in MSUD by decreasing mitochondrial KIC production.

Synthesis and reactions of triphenylphosphine-O-benzophenonimine and derivatives

International Nuclear Information System (INIS)

Elamin, Manahil Babiker

1999-08-01

O-Amino benzophenone and its para and meta isomers were prepared using Friedl-Craft benzoylation. Their azides were also prepared via their diazonium salts. The azide of o-amino benzophenone in its reduced form (o-benzylaniline) and its cyclic ketal were synthesised. All azides thus formed were reacted separately with triphenylphosphine to give the corresponding phosphinimines, the Wittig reagents nitrogen analog. The reactivity of the phosphorous bond. (P=N) in the different phosphoranes were studied by two types of reactions: (1) the Wittig type of reaction using benzaldehyde and its into derivatives with each of the above prepared phosphinimines. While triphenylphosphine-m-benzophenonimine (ii) and the triphenylphosphine benzophenonimine ethylene acetal (v) and it's reduced form triphenylphosphine-o-benzophenonimine (iv) react giving the corresponding schiffis bases. However, the ortho (i) and the para (iii) isomers failed to react. This lack of reactivity is presumably due to their great stability which came about through the extensive resonance that reduced the nucleophilicity of the nitrogen nucleophiles. (2) The phophinimines each was irradiated using Hanovia medium pressure UV lamp. Also the ortho and para isomers were not affected while others reacted giving the corresponding azo-compound and triphenylphosphine. they were separated and detected by chromatography.(Author)

Overview on mechanisms of acetic acid resistance in acetic acid bacteria.

Science.gov (United States)

Wang, Bin; Shao, Yanchun; Chen, Fusheng

2015-02-01

Acetic acid bacteria (AAB) are a group of gram-negative or gram-variable bacteria which possess an obligate aerobic property with oxygen as the terminal electron acceptor, meanwhile transform ethanol and sugar to corresponding aldehydes, ketones and organic acids. Since the first genus Acetobacter of AAB was established in 1898, 16 AAB genera have been recorded so far. As the main producer of a world-wide condiment, vinegar, AAB have evolved an elegant adaptive system that enables them to survive and produce a high concentration of acetic acid. Some researches and reviews focused on mechanisms of acid resistance in enteric bacteria and made the mechanisms thoroughly understood, while a few investigations did in AAB. As the related technologies with proteome, transcriptome and genome were rapidly developed and applied to AAB research, some plausible mechanisms conferring acetic acid resistance in some AAB strains have been published. In this review, the related mechanisms of AAB against acetic acid with acetic acid assimilation, transportation systems, cell morphology and membrane compositions, adaptation response, and fermentation conditions will be described. Finally, a framework for future research for anti-acid AAB will be provided.

Amino acid analysis in biological fluids by GC-MS

OpenAIRE

Kaspar, Hannelore

2009-01-01

Amino acids are intermediates in cellular metabolism and their quantitative analysis plays an important role in disease diagnostics. A gas chromatography-mass spectrometry (GC-MS) based method was developed for the quantitative analysis of free amino acids as their propyl chloroformate derivatives in biological fluids. Derivatization with propyl chloroformate could be carried out directly in the biological samples without prior protein precipitation or solid-phase extraction of the amino acid...

New insights into the mechanisms of acetic acid resistance in Acetobacter pasteurianus using iTRAQ-dependent quantitative proteomic analysis.

Science.gov (United States)

Xia, Kai; Zang, Ning; Zhang, Junmei; Zhang, Hong; Li, Yudong; Liu, Ye; Feng, Wei; Liang, Xinle

2016-12-05

Acetobacter pasteurianus is the main starter in rice vinegar manufacturing due to its remarkable abilities to resist and produce acetic acid. Although several mechanisms of acetic acid resistance have been proposed and only a few effector proteins have been identified, a comprehensive depiction of the biological processes involved in acetic acid resistance is needed. In this study, iTRAQ-based quantitative proteomic analysis was adopted to investigate the whole proteome of different acidic titers (3.6, 7.1 and 9.3%, w/v) of Acetobacter pasteurianus Ab3 during the vinegar fermentation process. Consequently, 1386 proteins, including 318 differentially expressed proteins (p150 proteins were differentially expressed. Specifically, proteins involved in amino acid metabolic processes and fatty acid biosynthesis were differentially expressed, which may contribute to the acetic acid resistance of Acetobacter. Transcription factors, two component systems and toxin-antitoxin systems were implicated in the modulatory network at multiple levels. In addition, the identification of proteins involved in redox homeostasis, protein metabolism, and the cell envelope suggested that the whole cellular system is mobilized in response to acid stress. These findings provide a differential proteomic profile of acetic acid resistance in Acetobacter pasteurianus and have potential application to highly acidic rice vinegar manufacturing. Copyright © 2016 Elsevier B.V. All rights reserved.

Relationship Between Structure and Antiproliferative Activity of Novel 5-amino-4-cyanopyrazole-1-formaldehydehydrazono Derivatives on HL-60RG Human Leukemia Cells.

Science.gov (United States)

Nagahara, Yukitoshi; Nagahara, Katsuhiko

2017-11-01

Pyrazole derivatives have been reported to have potent antimicrobial and anticancer activity. We recently synthesized and determined the effects of analogs, benzamidoxime derivatives, on mammalian cells and discovered that benzamidoximes had an antiproliferative effect. Here we synthesized and determined the anticancer effects of hydrazonopyrazole derivatives on a mammalian cancer cell line. We synthesized 12 hydrazonopyrazole derivatives with several constant alkyl chain length or branched chains at the side chain to investigate their anticancer cell activity, using the human myelogenous leukemia cell line HL-60RG. Among all hydrazonopyrazole derivatives we synthesized, the hydrazonopyrazole derivative with a branched chain at the side chain rather than a constant alkyl chain significantly inhibited cell viability. The strongest hydrazonopyrazole derivative, 5-amino-4-cyanopyrazole-1-formaldehydehydrazono-3'-pentanal, tended to damage cells dose-dependently. This cell growth attenuation was a result of apoptosis, activating caspase-3 and fragmented DNA. Hydrazonopyrazole derivatives induced apoptosis of HL-60RG leukemia cells. Copyright© 2017, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.

Human-derived gut microbiota modulates colonic secretion in mice by regulating 5-HT3 receptor expression via acetate production.

Science.gov (United States)

Bhattarai, Yogesh; Schmidt, Bradley A; Linden, David R; Larson, Eric D; Grover, Madhusudan; Beyder, Arthur; Farrugia, Gianrico; Kashyap, Purna C

2017-07-01

Serotonin [5-hydroxytryptamine (5-HT)], an important neurotransmitter and a paracrine messenger in the gastrointestinal tract, regulates intestinal secretion by its action primarily on 5-HT 3 and 5-HT 4 receptors. Recent studies highlight the role of gut microbiota in 5-HT biosynthesis. In this study, we determine whether human-derived gut microbiota affects host secretory response to 5-HT and 5-HT receptor expression. We used proximal colonic mucosa-submucosa preparation from age-matched Swiss Webster germ-free (GF) and humanized (HM; ex-GF colonized with human gut microbiota) mice. 5-HT evoked a significantly greater increase in short-circuit current (Δ I sc ) in GF compared with HM mice. Additionally, 5-HT 3 receptor mRNA and protein expression was significantly higher in GF compared with HM mice. Ondansetron, a 5-HT 3 receptor antagonist, inhibited 5-HT-evoked Δ I sc in GF mice but not in HM mice. Furthermore, a 5-HT 3 receptor-selective agonist, 2-methyl-5-hydroxytryptamine hydrochloride, evoked a significantly higher Δ I sc in GF compared with HM mice. Immunohistochemistry in 5-HT 3A -green fluorescent protein mice localized 5-HT 3 receptor expression to enterochromaffin cells in addition to nerve fibers. The significant difference in 5-HT-evoked Δ I sc between GF and HM mice persisted in the presence of tetrodotoxin (TTX) but was lost after ondansetron application in the presence of TTX. Application of acetate (10 mM) significantly lowered 5-HT 3 receptor mRNA in GF mouse colonoids. We conclude that host secretory response to 5-HT may be modulated by gut microbiota regulation of 5-HT 3 receptor expression via acetate production. Epithelial 5-HT 3 receptor may function as a mediator of gut microbiota-driven change in intestinal secretion. NEW & NOTEWORTHY We found that gut microbiota alters serotonin (5-HT)-evoked intestinal secretion in a 5-HT 3 receptor-dependent mechanism and gut microbiota metabolite acetate alters 5-HT 3 receptor expression in

Novel Type of alpha-Amino Acid Derived Imidazolium Ionic Liquids

Czech Academy of Sciences Publication Activity Database

Marek, Aleš; Bureš, F.; Kulhánek, J.

2014-01-01

Roč. 46, č. 21 (2014), s. 2937-2944 ISSN 0039-7881 Institutional support: RVO:61388963 Keywords : chiral ionic liquids * amino acid * imidazole * imidazolium salts * chiral pool Subject RIV: CC - Organic Chemistry Impact factor: 2.689, year: 2014

Synthesis and structure-activity studies on acidic amino acids and related diacids as NMDA receptor ligands

DEFF Research Database (Denmark)

Johansen, T N; Frydenvang, Karla Andrea; Ebert, B

1994-01-01

The 3-isoxazolol amino acids (S)-2-amino-3-(3-hydroxy-5-methyl-4- isoxazolyl)propionic acid [(S)-AMPA, 2] and (R,S)-2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic acid (AMAA, 5a) (Figure 1) are potent and specific agonists at the AMPA and N-methyl-D-aspartic acid (NMDA) subtypes, respectively......, of (S)-glutamic acid (1) receptors. A number of amino acids and diacids structurally related to AMAA were synthesized and tested electrophysiologically and in receptor-binding assays. The hydroxymethyl analogue 7c of AMAA was an NMDA agonist approximately equipotent with AMAA in the [3H...... by molecular mechanics calculations. Compound 7a possesses extra steric bulk and shows significant restriction of conformational flexibility compared to AMAA and 7c, which may be determining factors for the observed differences in biological activity. Although the nitrogen atom of quinolinic acid (6) has very...

Isoelectric focusing of dansylated amino acids in immobilized pH gradients

Science.gov (United States)

Bianchi-Bosisio, Adriana; Righetti, Pier Giorgio; Egen, Ned B.; Bier, Milan

1986-01-01

The 21 free amino acids commonly encountered in proteins have been transformed into 'carrier ampholyte' species by reacting their primary amino groups with dansyl chloride. These derivatives can thus be focused in an immobilized pH gradient covering the pH interval 3.1 to 4.1, except for arginine, which still retains a pI of 8.8. Due to their inherent fluorescence, the dansyl derivatives are revealed in UV light, with a sensitivity of the order of 2-4 ng/sq mm. All nearest neighbors are separated except for the following couples: Asn-Gln, Gly-Thr, Val-Ile and Cys-Cys2, with a resolving power, in a Delta(pI) scale, of the order of 0.0018 pH units. Except for a few cases (notably the aromatic amino acids), the order of pI values is well correlated with the pK values of carboxyl groups, suggesting that the latter are not altered by dansylation. From the set of pK(COOH)-pI values of the different amino acids, the pK of the tertiary amino group in the dansyl label has been calculated to be 5.11 + or - 0.06. Knowing the pK of the amino-dansyl and the pI of the excess, free dansyl label (pI = 3.34), a pK of 1.57 is derived for its sulfonic acid group.

Origin of second-order transverse magnetic anisotropy in Mn12-acetate

International Nuclear Information System (INIS)

Cornia, A.; Sessoli, R.; Sorace, L.; Gatteschi, D.; Barra, A. L.; Daiguebonne, C.

2002-01-01

The symmetry breaking effects for quantum tunneling of the magnetization in Mn 12 -acetate, a molecular nanomagnet, represent an open problem. We present structural evidence that the disorder of the acetic acid of crystallization induces sizable distortion of the Mn(III) sites, giving rise to six different isomers. Four isomers have symmetry lower than tetragonal and a nonzero second-order transverse magnetic anisotropy, which has been evaluated using a ligand field approach. The result of the calculation leads to an improved simulation of electron paramagnetic resonance spectra and justifies the tunnel splitting distribution derived from the field sweep rate dependence of the hysteresis loops

21 CFR 184.1185 - Calcium acetate.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Calcium acetate. 184.1185 Section 184.1185 Food and... Substances Affirmed as GRAS § 184.1185 Calcium acetate. (a) Calcium acetate (Ca (C2H3O2)2, CAS Reg. No. 62-54-4), also known as acetate of lime or vinegar salts, is the calcium salt of acetic acid. It may be...

In situ formation of the amino sugars 1-amino-1-deoxy-fructose and 2-amino-2-deoxy-glucose under Maillard reaction conditions in the absence of ammonia.

Science.gov (United States)

Nashalian, Ossanna; Yaylayan, Varoujan A

2016-04-15

Replacing amino acids with their binary metal complexes during the Maillard reaction can initiate various processes, including the oxidative degradation of their glucose conjugates, generating 1-amino-1-deoxy-fructose and its derivatives. These reactive amino sugars are not easily accessible under Maillard reaction conditions and are only formed in the presence of ammonia. To explore the generality of this observation and to study in particular the ability of fructose to generate glucosamine, the amino acid-metal complexes were heated in aqueous solutions with three aldohexoses and two ketohexoses at 110°C for 2 h and the dry residues were analysed by ESI/qTOF/MS/MS. All the sugars generated relatively intense ions at [M+H](+) 180 (C6H14NO5); those ions originating from ketohexoses exhibited MS/MS fragmentations identical to glucosamine and those originating form aldohexoses showed ions identical to fructosamine. Furthermore, the amino sugars were found to form fructosazine, react with other sugars and undergo dehydration reactions. Copyright © 2015 Elsevier Ltd. All rights reserved.

Phospholyl(borane) Amino Acids and Peptides: Stereoselective Synthesis and Fluorescent Properties with Large Stokes Shift.

Science.gov (United States)

Arribat, Mathieu; Rémond, Emmanuelle; Clément, Sébastien; Lee, Arie Van Der; Cavelier, Florine

2018-01-24

The synthesis of phospholyl(borane) amino acids was stereoselectively achieved by reaction of phospholide anion with iodo α-amino ester derived from l-aspartic acid or l-serine, followed by in situ complexation with borane. Phospholyl(borane) amino acids are easy to store and can be subjected to direct transformation into the corresponding free phospholyl, gold complex, oxide or sulfur derivatives as well as phospholinium salts, thus offering a variety of side chains. After selective deprotection of carboxylic function or amine, C- or N- peptide coupling with an alanine moiety proved the possible incorporation into peptides. Such phospholyl amino acid and peptide derivatives exhibit fluorescent properties with a large Stokes shift (160 nm) and fluorescence up to 535 nm, depending on the phosphole aromaticity and the chemical environment. These phospholyl(borane) amino acids constitute a new class of unnatural amino acids useful for structure-activities relationship studies and appear to be promising fluorophores for the development of labeled peptides.

Identification of acetates in elasmopalpulus lignosellus pheromone glands using a newly created mass spectral database and kóvats retention indices

Directory of Open Access Journals (Sweden)

Gulab N. Jham

2007-08-01

Full Text Available Based on a specially created mass spectral database utilizing 23 tetradecenyl and 22 hexadecenyl acetate standards along with Kóvats retention indices obtained on a very polar stationary phase [poly (biscyanopropyl siloxane] (SP 2340, (Z-9-hexadecenyl acetate, (Z-11-hexadecenyl acetate and (E-8-hexadecenyl acetate were identified in active pheromone extracts of Elasmopalpus lignosellus. This identification was more efficient than our previous study using gas chromatography/mass spectrometry with a dimethyl disulfide derivative where we could only identify the first two acetates. The acetate composition of the pheromone gland differed from region to region in Brazil and from that from the Tifton (GA, USA population, suggesting polymorphism or a different sub-species.

Automated calculation of myocardial external efficiency from a single 11C-acetate PET/CT scan

DEFF Research Database (Denmark)

Harms, Hans; Tolbod, Lars Poulsen; Hansson, Nils Henrik

of this study was to develop and validate an automated method of calculating MEE from a single dynamic 11C-acetate PETscan. Methods: 21 subjects underwent a dynamic 27 min 11C-acetate PETscan on a Siemens Biograph TruePoint 64 PET/CTscanner. Using cluster analysis, the LV-aortic time-activity curve (TACLV......). Conclusion: Myocardial efficiencycanbe derived directly andautomatically froma single dynamic 11C-acetate PET scan. This eliminates the need for a separate CMR scan and eliminates any potential errors due to different loading conditions between CMR and PETscans.......Background: Dynamic PETwith 11C-acetate can be used to assess myocardial oxygen use which in turn is usedto calculate myocardial external efficiency (MEE), anearly marker of heart failure. MEE is defined as the ratio of total work (TW) and total energy use (TE). Calculation of TW and TE requires...

Acetic acid removal from corn stover hydrolysate using ethyl acetate and the impact on Saccharomyces cerevisiae bioethanol fermentation.

Science.gov (United States)

Aghazadeh, Mahdieh; Ladisch, Michael R; Engelberth, Abigail S

2016-07-08

Acetic acid is introduced into cellulose conversion processes as a consequence of composition of lignocellulose feedstocks, causing significant inhibition of adapted, genetically modified and wild-type S. cerevisiae in bioethanol fermentation. While adaptation or modification of yeast may reduce inhibition, the most effective approach is to remove the acetic acid prior to fermentation. This work addresses liquid-liquid extraction of acetic acid from biomass hydrolysate through a pathway that mitigates acetic acid inhibition while avoiding the negative effects of the extractant, which itself may exhibit inhibition. Candidate solvents were selected using simulation results from Aspen Plus™, based on their ability to extract acetic acid which was confirmed by experimentation. All solvents showed varying degrees of toxicity toward yeast, but the relative volatility of ethyl acetate enabled its use as simple vacuum evaporation could reduce small concentrations of aqueous ethyl acetate to minimally inhibitory levels. The toxicity threshold of ethyl acetate, in the presence of acetic acid, was found to be 10 g L(-1) . The fermentation was enhanced by extracting 90% of the acetic acid using ethyl acetate, followed by vacuum evaporation to remove 88% removal of residual ethyl acetate along with 10% of the broth. NRRL Y-1546 yeast was used to demonstrate a 13% increase in concentration, 14% in ethanol specific production rate, and 11% ethanol yield. This study demonstrated that extraction of acetic acid with ethyl acetate followed by evaporative removal of ethyl acetate from the raffinate phase has potential to significantly enhance ethanol fermentation in a corn stover bioethanol facility. © 2016 American Institute of Chemical Engineers Biotechnol. Prog., 32:929-937, 2016. © 2016 American Institute of Chemical Engineers.

Obtaining of inulin acetate

OpenAIRE

Khusenov, Arslonnazar; Rakhmanberdiev, Gappar; Rakhimov, Dilshod; Khalikov, Muzaffar

2014-01-01

In the article first obtained inulin ester inulin acetate, by etherification of inulin with acetic anhydride has been exposed. Obtained product has been studied using elementary analysis and IR spectroscopy.

Effects of amino acids and vitamins on the ultrastructure of the hypothalamus and neurotransmitter in exhausted rats

Directory of Open Access Journals (Sweden)

Jian-wei CHEN

2012-01-01

Full Text Available Objective  To investigate the effects of amino acids and vitamins on the ultrastructure of the hypothalamus and neurotransmitter in exhausted rats. Methods  After adaptive swimming, 36 male SD rats were randomly divided into three groups, namely, capsule, control, and granules, with 12 rats in each group. Rats in 3 groups were given respectively amino acids capsule (8 kinds of essential amino acids and 11 kinds of vitamins were contained, normal drinking water, or amino acid-fructose beverage (2.5ml/100g, 2 times per day by gavage for 14 days. Exhaustion of rats was produced by non-loading swimming. The duration of the experiment lasted 14 days. After the last exhaustive swimming, the hypothalamus of the rats was removed for the observation of its ultrastructure under electron microscope. The contents of 5-hydroxytryptamine (5-HT, 5-hydroxyindole acetic acid (5HIAA, hydroxyphenyl acetic acid (HOPAC, and γ-aminobutyric acid (GABA in the hypothalamus were measured with high performance liquid chromatography (HPLC-ECD. Results  The mitochondrial structure in the brain cells of the capsule and granules groups were basically intact. On the other hand, the cells in the control group swelled and degenerated. Different degrees of swelling could be seen in the mitochondria. In addition, obvious morphological changes of the ultrastructure were observed under electron microscopy. Dissolution and rupture of the mitochondrial membrane and cristae were noted, even with the whole mitochondria disrupted and vacuolated. The contents of 5-HT, 5-HTAA, HOPAC, and GABA in the hypothalamus of rats in the capsule and the granules groups were significantly lower than those in the control group (PConclusion  Amino acids and vitamins compound can increase the resistance of the nerve center to fatigue by alleviating pathological changes of ultrastructure and changes in neurotransmitter levels of the hypothalamus.

Photochemical exchange reactions of thymine, uracil and their nucleosides with selected amino acids

International Nuclear Information System (INIS)

Shetlar, M.D.; Taylor, J.A.; Hom, K.

1984-01-01

The photoinduced exchange reactions of thymine with lysine at basic pH, using 254 nm light, have been studied. Three products have been isolated, namely, 6-amino-2-(1-thyminyl)hexanoic acid (Ia), 2-amino-6-(1-thyminyl)hexanoic acid (IIa) and 1-amino-5-(1-thyminyl)pentane (IIIa). Compound IIIa was shown to be a secondary product, produced by photochemical decarboxylation of Ia. Photochemical reaction of thymine with glycine and alanine at basic pH led, respectively, to formation of 2-(1-thyminyl)acetic acid (Ic) and 2-(1-thyminyl)propionic acid (Id). Compounds Ic and Id underwent photolysis to produce the decarboxylated secondary products 1-methylthymine and 1-ethylthymine, respectively. Thymidine reacts photochemically with glycine and alanine to produce the same products. Irradiation of DNA in the presence of lysine at basic pH led to the formation of the same products formed in the thymine-lysine system, namely Ia, IIa and IIIa. Uracil was found to undergo analogous photochemical exchange reactions with lysine to form 6-amino-2-(1-uracilyl)hexanoic acid (Ib), and 2-amino-6-(1-uracilyl)hexanoic acid (IIb). Compound Ib was found to undergo photodecarboxylation to form 1-amino-5-(1-uracilyl)pentane (IIIb), analogous to the secondary photoreaction of Ia. Photoreaction of uracil with 1,5-diaminopentane (cadaverine) likewise led to formation of IIIb. (author)

Experimental investigation of thermodynamic properties of binary mixture of acetic acid + n-butanol and acetic acid + water at temperature from 293.15 K to 343.15 K

Science.gov (United States)

Paul, M. Danish John; Shruthi, N.; Anantharaj, R.

2018-04-01

The derived thermodynamic properties like excess molar volume, partial molar volume, excess partial molar volume and apparent volume of binary mixture of acetic acid + n-butanolandacetic acid + water has been investigated using measured density of mixtures at temperatures from 293.15 K to 343.15.

Distribution of Amino Acids in Lunar Regolith

Science.gov (United States)

Elsila, J. E.; Callahan, M. P.; Glavin, D. P.; Dworkin, J. P.; Noble, S. K.; Gibson, E. K., Jr.

2014-01-01

One of the most eagerly studied questions upon initial return of lunar samples was whether significant amounts of organic compounds, including amino acids, were present. Analyses during the 1970s produced only tentative and inconclusive identifications of indigenous amino acids. Those analyses were hampered by analytical difficulties including relative insensitivity to certain compounds, the inability to separate chiral enantiomers, and the lack of compound-specific isotopic measurements, which made it impossible to determine whether the detected amino acids were indigenous to the lunar samples or the results of contamination. Numerous advances have been made in instrumentation and methodology for amino acid characterization in extraterrestrial samples in the intervening years, yet the origin of amino acids in lunar regolith samples has been revisited only once for a single lunar sample, (3) and remains unclear. Here, we present initial data from the analyses of amino acid abundances in 12 lunar regolith samples. We discuss these abundances in the context of four potential amino acid sources: (1) terrestrial biological contamination; (2) contamination from lunar module (LM) exhaust; (3) derivation from solar windimplanted precursors; and (4) exogenous delivery from meteorites.

Polymerization of amino acids containing nucleotide bases

Science.gov (United States)

Ben Cheikh, Azzouz; Orgel, Leslie E.

1990-01-01

The nucleoamino acids 1-(3'-amino,3'-carboxypropyl)uracil (3) and 9-(3'-amino,3'-carboxypropyl)adenine (4) have been prepared as (L)-en-antiomers and as racemic mixtures. When 3 or 4 is suspended in water and treated with N,N'-carbon-yldiimidazole, peptides are formed in good yield. The products formed from the (L)-enantiomers are hydrolyzed to the monomeric amino acids by pronase. Attempts to improve the efficiency of these oligomerizations by including a polyuridylate template in the reaction mixture were not successful. Similarly, oligomers derived from the (L)-enantiomer of 3 did not act as templates to facilitate the oligomerization of 4.

Potential Grape-Derived Contributions to Volatile Ester Concentrations in Wine

Directory of Open Access Journals (Sweden)

Paul K. Boss

2015-04-01

Full Text Available Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg∙L−1 β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg∙L−1 β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg∙L−1 required for the stimulatory effect on ethyl and acetate ester production observed in this study.

Potential grape-derived contributions to volatile ester concentrations in wine.

Science.gov (United States)

Boss, Paul K; Pearce, Anthony D; Zhao, Yanjia; Nicholson, Emily L; Dennis, Eric G; Jeffery, David W

2015-04-29

Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg∙L(-1) β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg∙L(-1) β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg∙L(-1) required for the stimulatory effect on ethyl and acetate ester production observed in this study.

Effectiveness of Alkaline Pretreatment and Acetic Acid Hydrolysis on the Characteristics of Collagen from Fish Skin of Snakehead

Directory of Open Access Journals (Sweden)

Wulandari

2015-12-01

Full Text Available Fish skin is one of marine byproducts potential for alternative source of collagen. This study investigated the effectiveness of alkaline and acetic acid pretreatment on the characteristics of collagen from skin snakehead fish. The concentrations of alkaline pretreatment were 0.05; 0.1; 0.15 and 0.2 M for 2, 4, 6, 8, 10 and 12 hours, acetic acid concentrations were 0.05 M, 0.1 M, 0.15 M and 0.2 M for 1 and 2 hours. The experimental design used for alkaline and acetic acid pretreatment was factorial completely randomized design. The result showed that the concentration of alkaline 0.05 M for 6 hours have significant effect on the elimination of non-collagen protein (p<0.05, whereas for the optimum acetic acid at a concentration 0.1 M for 2 hours significantly different on solubility and swelling. Extraction yields of collagen was 16%, with characteristics of whiteness 66.67%, protein content 96.21%, viscosity 10 cP, Tmax 159.9oC and glass transition temperature 78.55oC. The dominant amino acid composition were glycine (27.11%, proline (13.87% and alanine (12.58%. Functional groups collagen from skin snakehead fish has β-sheet structure which is a characteristic of collagen.

Effectiveness of Alkaline Pretreatment and Acetic Acid Hydrolysis on the Characteristics of Collagen from Fish Skin of Snakehead

Directory of Open Access Journals (Sweden)

Wulandari Wulandari

2015-12-01

Full Text Available Fish skin is one of marine byproducts potential for alternative source of collagen. This studyinvestigated the effectiveness of alkaline and acetic acid pretreatment on the characteristics ofcollagen from skin snakehead fish. The concentrations of alkaline pretreatment were 0.05; 0.1; 0.15and 0.2 M for 2, 4, 6, 8, 10 and 12 hours, acetic acid concentrations were 0.05 M, 0.1 M, 0.15 M and0.2 M for 1 and 2 hours. The experimental design used for alkaline and acetic acid pretreatmentwas factorial completely randomized design. The result showed that the concentration of alkaline0.05 M for 6 hours have significant effect on the elimination of non-collagen protein (p<0.05,whereas for the optimum acetic acid at a concentration 0.1 M for 2 hours significantly differenton solubility and swelling. Extraction yields of collagen was 16%, with characteristics of whiteness66.67%, protein content 96.21%, viscosity 10 cP, Tmax 159.9oC and glass transition temperature78.55oC. The dominant amino acid composition were glycine (27.11%, proline (13.87% andalanine (12.58%. Functional groups collagen from skin snakehead fish has β-sheet structurewhich is a characteristic of collagen.

Characterization of acetate-utilizing methanogenic bacteria, depending on varying acetate concentrations, in a biogas plant. Phase 1

International Nuclear Information System (INIS)

Ahring, B.K.

1994-12-01

The present report contains the results of a project concerning behaviour of acetate-utilizing methanogenic bacteria in mesophilic and thermophilic biogas plants, collected in 1992 - 1994 period. Labelled acetates (2-C 14 -CH 3 COOH) have been used to characterize the types of methane bacteria populations in the Danish biogas plants, the optimum acetate concentration for these bacteria and acetate metabolism in mesophilic and thermophilic biogas reactors with low acetate concentrations. 2 publications are included. (EG)

ACETIC ACID AND A BUFFER

DEFF Research Database (Denmark)

2009-01-01

The present invention relates to a composition comprising : a) 0.01-20% wt/wt acetic acid and b) a physiologically tolerable buffer capable of maintaining acetic acid at a pH in the range of 2-7; and use of such a composition as an antimicrobial agent.......The present invention relates to a composition comprising : a) 0.01-20% wt/wt acetic acid and b) a physiologically tolerable buffer capable of maintaining acetic acid at a pH in the range of 2-7; and use of such a composition as an antimicrobial agent....

Determinants of the acetate recovery factor: implications for estimation of 13C substrate oxidation.

NARCIS (Netherlands)

P. Schrauwen; E.E. Blaak; A.J.M. Wagenmakers; dr. Lars B. Borghouts; D.P.C. van Aggel-Leijssen

2000-01-01

The data of this study indicate that the acetate recovery factor, used in stable isotope research, needs to be deteremined in every subject, under similar conditions as used for the tracer-derived determination of substrate oxidation.

Glycerol acetals, kinetic study of the reaction between glycerol and formaldehyde

International Nuclear Information System (INIS)

Agirre, I.; Garcia, I.; Requies, J.; Barrio, V.L.; Gueemez, M.B.; Cambra, J.F.; Arias, P.L.

2011-01-01

The acetalization reaction between glycerol and formaldehyde using Amberlyst 47 acidic ion exchange resin was studied. These acetals can be obtained from renewable sources (bioalcohols and bioalcohol derived aldehydes) and seem to be good candidates for different applications such as oxygenated diesel additives. A preliminary kinetic study was performed in a batch stirred tank reactor studying the influence of different process parameters like temperature, feed composition and the stirring speed. A pseudo homogenous kinetic model able to explain the reaction mechanism was adjusted. Thus, the corresponding order of reaction was determined. Amberlyst 47 acidic ion exchange resin showed a fairly good behavior allowing 100% of selectivity towards acetals formation. However, the studied acetalization reaction showed high thermodynamic limitations achieving glycerol conversions around 50% using a stoichiometric feed ratio at 353 K. The product is a mixture of two isomers (1,3-Dioxan-5-ol and 1,3-dioxolane-4-methanol) and the conversion of 1,3-dioxolane-4-methanol into 1,3-Dioxan-5-ol was also observed. -- Highlights: → The reaction between glycerol and acetaldehyde shows thermodynamic limitations. → Amberlyst 47 ion exchange resins show 100% of selectivity. → A pseudo-homogeneous kinetic model is able to predict the reaction progress. → Isomerization reactions were observed from dioxalanes to dioxanes.

[Research of imidazo[1,2-a]benzimidazole derivatives. XXX. Synthesis and properties of (imidazo[1,2-a]benzimidazolyl-2)acetic acid derivatives].

Science.gov (United States)

Anisimova, V A; Tolpygin, I E; Spasov, A A; Serdiuk, T S; Sukhov, A G

2011-01-01

Ethyl esters of (9-subtituted-imidazo[1,2-a]benzimidazolyl-2)acetic acids were synthesized. The chemical properties of these esters (hydrolysis, decarboxylation, hydrazinolysis) and biological activity (fungicidal, antimicrobial, antiarrhythmic activity, and also affects on the brain rhythmogenesis) of the prepared compounds were studied.

Urinary amino acid analysis: a comparison of iTRAQ-LC-MS/MS, GC-MS, and amino acid analyzer.

Science.gov (United States)

Kaspar, Hannelore; Dettmer, Katja; Chan, Queenie; Daniels, Scott; Nimkar, Subodh; Daviglus, Martha L; Stamler, Jeremiah; Elliott, Paul; Oefner, Peter J

2009-07-01

Urinary amino acid analysis is typically done by cation-exchange chromatography followed by post-column derivatization with ninhydrin and UV detection. This method lacks throughput and specificity. Two recently introduced stable isotope ratio mass spectrometric methods promise to overcome those shortcomings. Using two blinded sets of urine replicates and a certified amino acid standard, we compared the precision and accuracy of gas chromatography/mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) of propyl chloroformate and iTRAQ derivatized amino acids, respectively, to conventional amino acid analysis. The GC-MS method builds on the direct derivatization of amino acids in diluted urine with propyl chloroformate, GC separation and mass spectrometric quantification of derivatives using stable isotope labeled standards. The LC-MS/MS method requires prior urinary protein precipitation followed by labeling of urinary and standard amino acids with iTRAQ tags containing different cleavable reporter ions distinguishable by MS/MS fragmentation. Means and standard deviations of percent technical error (%TE) computed for 20 amino acids determined by amino acid analyzer, GC-MS, and iTRAQ-LC-MS/MS analyses of 33 duplicate and triplicate urine specimens were 7.27+/-5.22, 21.18+/-10.94, and 18.34+/-14.67, respectively. Corresponding values for 13 amino acids determined in a second batch of 144 urine specimens measured in duplicate or triplicate were 8.39+/-5.35, 6.23+/-3.84, and 35.37+/-29.42. Both GC-MS and iTRAQ-LC-MS/MS are suited for high-throughput amino acid analysis, with the former offering at present higher reproducibility and completely automated sample pretreatment, while the latter covers more amino acids and related amines.

Contact allergy to isoeugenol and its derivatives

DEFF Research Database (Denmark)

Tanaka, Susumu; Royds, C; Buckley, Christopher D

2004-01-01

A total of 2261 (808 male, 1453 female) consecutive patients attending contact dermatitis clinics were patch tested to isoeugenol and its derivatives listed in the EU Inventory of Fragrance Ingredients. Positive reactions were found to isoeugenol in 40, transisoeugenol in 40, isoeugenyl acetate...... and 15/16 of those to isoeugenyl phenylacetate but in none of those 6 positive to isoeugenyl methyl ether and in neither of those 2 positive to benzyl isoeugenyl ether. Concomitant contact allergy between isoeugenol and its derivatives may occur through chemical cross-reactivity or local skin metabolism...... of the derivatives. It is more commonly observed with the esters rather than the ethers. Isoeugenyl acetate has been proposed as an alternative to isoeugenol, but there is a high degree of concomitant reactivity with isoeugenol....

Distal, not proximal, colonic acetate infusions promote fat oxidation and improve metabolic markers in overweight/obese men

DEFF Research Database (Denmark)

van der Beek, Christina M; Canfora, Emanuel E; Lenaerts, Kaatje

2016-01-01

, circulating hormones or inflammatory markers. In conclusion distal colonic acetate infusions affected whole-body substrate metabolism, with a pronounced increase in fasting fat oxidation and plasma PYY. Modulating colonic acetate may be a nutritional target to treat or prevent metabolic disorders.......Gut microbial-derived short-chain fatty acids (SCFA) are believed to affect host metabolism and cardiometabolic risk factors. The present study aim was to investigate the effects of proximal and distal colonic infusions with the SCFA acetate on fat oxidation and other metabolic parameters in men...... in the colon for three consecutive test days, enabling colonic acetate (100 or 180 mmol/l) or placebo infusion during fasting conditions and after an oral glucose load (postprandial). Fat oxidation and energy expenditure were measured using an open-circuit ventilated hood system and blood samples were...

Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.

Science.gov (United States)

Lu, Deng-Fu; Zhu, Cheng-Liang; Jia, Zhen-Xin; Xu, Hao

2014-09-24

An iron-catalyzed diastereoselective intermolecular olefin amino-oxygenation reaction is reported, which proceeds via an iron-nitrenoid generated by the N-O bond cleavage of a functionalized hydroxylamine. In this reaction, a bench-stable hydroxylamine derivative is used as the amination reagent and oxidant. This method tolerates a range of synthetically valuable substrates that have been all incompatible with existing amino-oxygenation methods. It can also provide amino alcohol derivatives with regio- and stereochemical arrays complementary to known amino-oxygenation methods.

Development of 1-Amino-4-(phenylamino)anthraquinone-2-sulfonate Sodium Derivatives as a New Class of Inhibitors of RANKL-Induced Osteoclastogenesis.

Science.gov (United States)

Lee, Chia-Chung; Chen, Chun-Liang; Liu, Fei-Lan; Chiou, Chung-Yu; Chen, Tsung-Chih; Wu, Cheng-Chi; Sun, Wei-Hsin; Chang, Deh-Ming; Huang, Hsu-Shan

2016-05-01

A series of 1-amino-4-(phenylamino)anthraquinone-2-sulfonate sodium derivatives was synthesized and evaluated for osteoclast inhibition using a TRAP-staining assay. Among them, two compounds, LCCY-13 and LCCY-15, dose-dependently suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclast formation. Moreover, the cytotoxicity assay on RAW264.7 cells suggested that the inhibition of osteoclastic bone resorption by these compounds was not a result of their cytotoxicity. Further, the inhibitory activities of compounds LCCY-13 and LCCY-15 were further confirmed by including specific inhibition of NFATc1 expression levels in nuclei using an immunofluorescent analysis. In addition, LCCY-13 and LCCY-15 also significantly attenuated the bone resorption activity of osteoclasts according to a pit formation assay. Thus, a new class of 1-amino-4-(phenylamino)anthraquinone-2-sulfonate sodium compounds might be considered as an essential lead structure for the further development of anti-resorptive agents. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Identification of novel potential acetate-oxidizing bacteria in an acetate-fed methanogenic chemostat based on DNA stable isotope probing.

Science.gov (United States)

Wang, Hui-Zhong; Gou, Min; Yi, Yue; Xia, Zi-Yuan; Tang, Yue-Qin

2018-05-11

Acetate is a significant intermediate of anaerobic fermentation. There are two pathways for converting acetate to CH 4 and CO 2 : acetoclastic methanogenesis by acetoclastic methanogens, and syntrophic acetate oxidation by acetate-oxidizing bacteria (AOB) and hydrogenotrophic methanogens. Detailed investigations of syntrophic acetate-oxidizing bacteria (SAOB) should contribute to the elucidation of the microbial mechanisms of methanogenesis. In this study, we investigated the major phylogenetic groups of acetate-utilizing bacteria (AUB) in a mesophilic methanogenic chemostat fed with acetate as the sole carbon source by using DNA stable isotope probing (SIP) technology. The results indicated that acetoclastic methanogenesis and acetate oxidization/hydrogenotrophic methanogenesis coexisted in the mesophilic chemostat fed with acetate, operated at a dilution rate of 0.1 d -1 . OTU Ace13(9-17) (KU869530), Ace13(9-4) (KU667241), and Ace13(9-23) (KU667236), assigned to the phyla Firmicutes and Bacteroidetes, were probably potential SAOB in the chemostat, which needs further investigation. Species in the phyla Proteobacteria, Deferribacteres, Acidobacteria, Spirochaetes and Actinobacteria were probably capable of utilizing acetate for their growth. Methanoculleus was likely to be the preferred hydrogenotrophic methanogen for syntrophy with AOB in the chemostat.

Urinary Amino Acid Analysis: A Comparison of iTRAQ®-LC-MS/MS, GC-MS, and Amino Acid Analyzer

Science.gov (United States)

Kaspar, Hannelore; Dettmer, Katja; Chan, Queenie; Daniels, Scott; Nimkar, Subodh; Daviglus, Martha L.; Stamler, Jeremiah; Elliott, Paul; Oefner, Peter J.

2009-01-01

Urinary amino acid analysis is typically done by cation-exchange chromatography followed by post-column derivatization with ninhydrin and UV detection. This method lacks throughput and specificity. Two recently introduced stable isotope ratio mass spectrometric methods promise to overcome those shortcomings. Using two blinded sets of urine replicates and a certified amino acid standard, we compared the precision and accuracy of gas chromatography/mass spectrometry (GC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS) of propyl chloroformate and iTRAQ® derivatized amino acids, respectively, to conventional amino acid analysis. The GC-MS method builds on the direct derivatization of amino acids in diluted urine with propyl chloroformate, GC separation and mass spectrometric quantification of derivatives using stable isotope labeled standards. The LC-MS/MS method requires prior urinary protein precipitation followed by labeling of urinary and standard amino acids with iTRAQ® tags containing different cleavable reporter ions distinguishable by MS/MS fragmentation. Means and standard deviations of percent technical error (%TE) computed for 20 amino acids determined by amino acid analyzer, GC-MS, and iTRAQ®-LC-MS/MS analyses of 33 duplicate and triplicate urine specimens were 7.27±5.22, 21.18±10.94, and 18.34±14.67, respectively. Corresponding values for 13 amino acids determined in a second batch of 144 urine specimens measured in duplicate or triplicate were 8.39±5.35, 6.23±3.84, and 35.37±29.42. Both GC-MS and iTRAQ®-LC-MS/MS are suited for high-throughput amino acid analysis, with the former offering at present higher reproducibility and completely automated sample pretreatment, while the latter covers more amino acids and related amines. PMID:19481989

Repair of oxidative DNA damage by amino acids.

Science.gov (United States)

Milligan, J R; Aguilera, J A; Ly, A; Tran, N Q; Hoang, O; Ward, J F

2003-11-01

Guanyl radicals, the product of the removal of a single electron from guanine, are produced in DNA by the direct effect of ionizing radiation. We have produced guanyl radicals in DNA by using the single electron oxidizing agent (SCN)2-, itself derived from the indirect effect of ionizing radiation via thiocyanate scavenging of OH. We have examined the reactivity of guanyl radicals in plasmid DNA with the six most easily oxidized amino acids cysteine, cystine, histidine, methionine, tryptophan and tyrosine and also simple ester and amide derivatives of them. Cystine and histidine derivatives are unreactive. Cysteine, methionine, tyrosine and particularly tryptophan derivatives react to repair guanyl radicals in plasmid DNA with rate constants in the region of approximately 10(5), 10(5), 10(6) and 10(7) dm3 mol(-1) s(-1), respectively. The implication is that amino acid residues in DNA binding proteins such as histones might be able to repair by an electron transfer reaction the DNA damage produced by the direct effect of ionizing radiation or by other oxidative insults.

One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach.

Science.gov (United States)

Shanmugaraju, Sankarasekaran; McAdams, Deirdre; Pancotti, Francesca; Hawes, Chris S; Veale, Emma B; Kitchen, Jonathan A; Gunnlaugsson, Thorfinnur

2017-09-13

We report here a novel one-pot synthetic strategy for the synthesis of a family of N-alkyl-1,8-naphthalimide based Tröger's bases via a nucleophilic substitution reaction of a common 'precursor' (or a 'synthon') N-aryl-1,8-naphthalimide Tröger's base heated at 80 °C in neat aliphatic primary amine, in overall yield of 65-96%. This methodology provides an efficient and one-step facile route to design 1,8-naphthalimide derived Tröger's base structures in analytically pure form without the use of column chromatography purification, that can be used in medicinal chemistry and as supramolecular scaffolds. We also report the formation of the corresponding anhydride, and the crystallographic analysis of two of the resulting products, that of the N-phenyl-4-amino-1,8-naphthalimide and the anhydride derived Tröger's bases.

Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives

Science.gov (United States)

Larksarp; Alper

2000-05-09

A catalyst system comprising palladium acetate-bidentate phosphine is effective for the cyclocarbonylation of o-iodoanilines with heterocumulenes at 70-100 degrees C for 12-24 h to give the corresponding 4(3H)-quinazolinone derivatives in good yields. Utilizing o-iodoaniline with isocyanates, carbodiimides, and ketenimines for the reaction, 2,4-(1H,3H)-quinazolinediones, 2-amino-4(3H)-quinazolinones and 2-alkyl-4(3H)-quinazolinones were obtained, respectively. The nature of the substrates including the electrophilicity of the carbon center of the carbodiimide, and the stability of the ketenimine, influence the product yields of this reaction. Urea-type intermediates are believed to be generated first in situ from the reaction of o-iodoanilines with heterocumulenes, followed by palladium-catalyzed carbonylation and cyclization to yield the products.

Improving the expression of recombinant proteins in E. coli BL21 (DE3) under acetate stress: an alkaline pH shift approach.

Science.gov (United States)

Wang, Hengwei; Wang, Fengqing; Wang, Wei; Yao, Xueling; Wei, Dongzhi; Cheng, Hairong; Deng, Zixin

2014-01-01

Excess acetate has long been an issue for the production of recombinant proteins in E. coli cells. Recently, improvements in acetate tolerance have been achieved through the use of genetic strategies and medium supplementation with certain amino acids and pyrimidines. The aim of our study was to evaluate an alternative to improve the acetate tolerance of E. coli BL21 (DE3), a popular strain used to express recombinant proteins. In this work we reported the cultivation of BL21 (DE3) in complex media containing acetate at high concentrations. In the presence of 300 mM acetate, compared with pH 6.5, pH 7.5 improved cell growth by approximately 71%, reduced intracellular acetate by approximately 50%, and restored the expression of glutathione S-transferase (GST), green fluorescent protein (GFP) and cytochrome P450 monooxygenase (CYP). Further experiments showed that alkaline pHs up to 8.5 had little inhibition in the expression of GST, GFP and CYP. In addition, the detrimental effect of acetate on the reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) by the cell membrane, an index of cellular metabolic capacity, was substantially alleviated by a shift to alkaline pH values of 7.5-8.0. Thus, we suggest an approach of cultivating E. coli BL21 (DE3) at pH 8.0 ± 0.5 to minimize the effects caused by acetate stress. The proposed strategy of an alkaline pH shift is a simple approach to solving similar bioprocessing problems in the production of biofuels and biochemicals from sugars.

Identification of a novel acetate-utilizing bacterium belonging to Synergistes group 4 in anaerobic digester sludge.

Science.gov (United States)

Ito, Tsukasa; Yoshiguchi, Kazumi; Ariesyady, Herto Dwi; Okabe, Satoshi

2011-12-01

Major acetate-utilizing bacterial and archaeal populations in methanogenic anaerobic digester sludge were identified and quantified by radioisotope- and stable-isotope-based functional analyses, microautoradiography-fluorescence in situ hybridization (MAR-FISH) and stable-isotope probing of 16S rRNA (RNA-SIP) that can directly link 16S rRNA phylogeny with in situ metabolic function. First, MAR-FISH with (14)C-acetate indicated the significant utilization of acetate by only two major groups, unidentified bacterial cells and Methanosaeta-like filamentous archaeal cells, in the digester sludge. To identify the acetate-utilizing unidentified bacteria, RNA-SIP was conducted with (13)C(6)-glucose and (13)C(3)-propionate as sole carbon source, which were followed by phylogenetic analysis of 16S rRNA. We found that bacteria belonging to Synergistes group 4 were commonly detected in both 16S rRNA clone libraries derived from the sludge incubated with (13)C-glucose and (13)C-propionate. To confirm that this bacterial group can utilize acetate, specific FISH probe targeting for Synergistes group 4 was newly designed and applied to the sludge incubated with (14)C-acetate for MAR-FISH. The MAR-FISH result showed that bacteria belonging to Synergistes group 4 significantly took up acetate and their active population size was comparable to that of Methanosaeta in this sludge. In addition, as bacteria belonging to Synergistes group 4 had high K(m) for acetate and maximum utilization rate, they are more competitive for acetate over Methanosaeta at high acetate concentrations (2.5-10  mM). To our knowledge, it is the first time to report the acetate-utilizing activity of uncultured bacteria belonging to Synergistes group 4 and its competitive significance to acetoclastic methanogen, Methanosaeta.

Design, Synthesis and DFT/DNP Modeling Study of New 2-Amino-5-arylazothiazole Derivatives as Potential Antibacterial Agents

Directory of Open Access Journals (Sweden)

Sraa Abu-Melha

2018-02-01

Full Text Available A new series of 2-amino-5-arylazothiazole derivatives has been designed and synthesized in 61–78% yields and screened as potential antibacterial drug candidates against the Gram negative bacterium Escherichia coli. The geometry of the title compounds were being studied using the Material Studio package and semi-core pseudopods calculations (dspp were performed with the double numerica basis sets plus polarization functional (DNP to predict the properties of materials using the hybrid FT/B3LYP method. Modeling calculations, especially the (EH-EL difference and the energetic parameters revealed that some of the title compounds may be promising tools for further research work and the activity is structure dependent.

Anthrarobin and its derivatives: evaluation of antibacterial and lipoxygenase inhibition activities

International Nuclear Information System (INIS)

Lateef, M.; Iqbal, S.

2013-01-01

The antibacterial activity of anthrarobin and its synthesized derivatives 1, 10-dihydoxyanthracen-2-0-acetate (1) and anthracen-1, 2-10-tri-O-acetate (2) is determined against two Gram-negative bacteria (Escherichia coli, Pseudomonas aerogenosa) and two Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis) along with the lipoxygenase inhibition activity. Gentamycin (0.3 %) was used as standard antibiotic for antibacterial assay. The minimum inhibitory concentration (MIC) was determined by agar well diffusion method. Anthrarobin showed highest antibacterial activity against all the tested bacteria while anthracen-1, 2-10-tri-0-acetate (2) exhibited 97 % activity against Gram-positive bacteria, Staphylococcus aureus, and; 36 % activity against Gram-negative bacteria Escherichia coli. On the other hand, 1, 10-dihydoxyanthracen-2-0-acetate (1) remained non-significant against all the bacteria tested. When anthrarobin and its derivatives were analyzed for lipoxygenase inhibition studies, only anthrarobin showed weak inhibition activity with IC 5 0 value of 65.2 μM. It is concluded that anthrarobin has significant potential for antibacterial activity as compared to its synthesized derivatives. Structure-activity relationship suggests that numbers of hydroxyl group in anthrarobin may be responsible for antimicrobial activity and the activity decreases with the substitution of acyl groups in synthesized derivatives. (author)

Indole-3-acetic acid biosynthetic pathway and aromatic amino acid aminotransferase activities in Pantoea dispersa strain GPK.

Science.gov (United States)

Kulkarni, G B; Nayak, A S; Sajjan, S S; Oblesha, A; Karegoudar, T B

2013-05-01

This investigation deals with the production of IAA by a bacterial isolate Pantoea dispersa strain GPK (PDG) identified by 16S rRNA gene sequence analysis. HPLC and Mass spectral analysis of metabolites from bacterial spent medium revealed that, IAA production by PDG is Trp-dependent and follows indole-3-pyruvic acid (IPyA) pathway. Substrate specificity study of aromatic amino acid aminotransferase (AAT) showed high activities, only when tryptophan (Trp) and α-ketoglutarate (α-kg) were used as substrates. AAT is highly specific for Trp and α-kg as amino group donor and acceptor, respectively. The effect of exogenous IAA on bacterial growth was established. Low concentration of exogenous IAA induced the growth, whereas high concentration decreased the growth of bacterium. PDG treatment significantly increased the root length, shoot length and dry mass of the chickpea and pigeon pea plants. © 2013 The Society for Applied Microbiology.

Synthesis of O-Amino Sugars and Nucleosides

Directory of Open Access Journals (Sweden)

Na Chen

2018-03-01

Full Text Available Nucleic acids and carbohydrates are essential biomolecules involved in numerous biological and pathological processes. Development of multifunctional building blocks based on nucleosides and sugars is in high demand for the generation of novel oligonucleotide mimics and glycoconjugates for biomedical applications. Recently, aminooxyl-functionalized compounds have attracted increasing research interest because of their easy derivatization through oxime ligation or N-oxyamide formation reactions. Various biological applications have been reported for O-amino carbohydrate- and nucleoside-derived compounds. Here, we report our efforts in the design and synthesis of glyco-, glycosyl, nucleoside- and nucleo-aminooxy acid derivatives from readily available sugars and amino acids, and their use for the generation of N-oxyamide-linked oligosaccharides, glycopeptides, glycolipids, oligonucleosides and nucleopeptides as novel glycoconjugates or oligonucleotide mimics. Delicate and key points in the synthesis will be emphasized.

Synthesis and characterization of mixed ligand Cu(II) complexes of salicylic acid derivatives with 2-aminobenzotiyazol derivatives

OpenAIRE

İlkimen, Halil; Yenikaya, Cengiz

2018-01-01

In thisstudy, mixed ligand transitionmetal complexes of Cu(II)have been prepared between salicylic acid derivatives [salicylic acid (H2sal) or acetylsalicylic acid (Hasal)] and 2-aminobenzothiazole derivatives[2-aminobenzothiazole (abt) or 2-amino-6-chlorobenzothiazole (Clabt) or2-amino-6-methylbenzothiazole (Meabt)]. The structures of amorphous metalcomplexes have been proposed by evaluating the data obtained from elementalanalysis, ICP-OES, FT-IR, UV-Vis, thermal analysis, magnetic suscepti...

21 CFR 582.6185 - Calcium acetate.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Calcium acetate. 582.6185 Section 582.6185 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL... Calcium acetate. (a) Product. Calcium acetate. (b) Conditions of use. This substance is generally...

Measurement of local cerebral protein synthesis in vivo: influence of recycling of amino acids derived from protein degradation

International Nuclear Information System (INIS)

Smith, C.B.; Deibler, G.E.; Eng, N.; Schmidt, K.; Sokoloff, L.

1988-01-01

A quantitative autoradiographic method for the determination of local rates of protein synthesis in brain in vivo is being developed. The method employs L-[1- 14 C]leucine as the radiolabeled tracer. A comprehensive model has been designed that takes into account intracellular and extracellular spaces, intracellular compartmentation of leucine, and the possibility of recycling of unlabeled leucine derived from steady-state degradation of protein into the precursor pool for protein synthesis. We have evaluated the degree of recycling by measuring the ratio of the steady-state precursor pool distribution space for labeled leucine to that of unlabeled leucine. The values obtained were 0.58 in whole brain and 0.47 in liver. These results indicate that there is significant recycling of unlabeled amino acids derived from steady-state protein degradation in both tissues. Any method for the determination of rates of cerebral protein synthesis in vivo with labeled tracers that depends on estimation of precursor pool specific activity in tissue from measurements in plasma must take this recycling into account

Are phloem-derived amino acids the origin of the elevated malate concentration in the xylem sap following mineral N starvation in soybean?

Science.gov (United States)

Vitor, Simone C; do Amarante, Luciano; Sodek, Ladaslav

2018-05-16

A substantial increase in malate in the xylem sap of soybean subjected to mineral N starvation originates mainly from aspartate, a prominent amino acid of the phloem. A substantial increase in xylem malate was found when non-nodulated soybean plants were transferred to a N-free medium. Nodulated plants growing in the absence of mineral N and, therefore, dependent on symbiotic N 2 fixation also contained elevated concentrations of malate in the xylem sap. When either nitrate or ammonium was supplied, malate concentrations in the xylem sap were low, both for nodulated and non-nodulated plants. Evidence was obtained that the elevated malate concentration of the xylem was derived from amino acids supplied by the phloem. Aspartate was a prominent component of the phloem sap amino acids and, therefore, a potential source of malate. Supplying the roots of intact plants with 13 C-aspartate revealed that malate of the xylem sap was readily labelled under N starvation. A hypothetical scheme is proposed whereby aspartate supplied by the phloem is metabolised in the roots and the products of this metabolism cycled back to the shoot. Under N starvation, aspartate metabolism is diverted from asparagine synthesis to supply N for the synthesis of other amino acids via transaminase activity. The by-product of aspartate transaminase activity, oxaloacetate, is transformed to malate and its export accounts for much of the elevated concentration of malate found in the xylem sap. This mechanism represents a new additional role for malate during mineral N starvation of soybean, beyond that of charge balance.

An improved synthesis of 1,3,5-triaryl-2-pyrazolines in acetic acid aqueous solution under ultrasound irradiation

Directory of Open Access Journals (Sweden)

Lin Zhi-Ping

2007-03-01

Full Text Available Abstract Background Pyrazoline derivatives have been found to possess a broad spectrum of biological activities. Among various pyrazoline derivatives, 2-pyrazolines seem to be the most frequently studied. A variety of methods have been reported for the preparation of this class of compound. However, in spite of their potential utility, some of the reported methods suffer from drawbacks such as long reaction times, cumbersome product isolation procedures and environmental concerns. Organic reactions in aqueous media have attracted increasing interest recently because of environmental issues and the understanding of biochemical processes. Ultrasound has increasingly been used in organic synthesis in the last three decades. A large number of organic reactions can be carried out in higher yields, shorter reaction time or milder conditions under ultrasound irradiation. Results Preparation of a series of 1,3,5-triaryl-2-pyrazolines through the reaction of chalcones and phenylhydrazine hydrochloride was carried out in 83–96% yield within 1.5–2 h in sodium acetate-acetic acid aqueous solution under ultrasound irradiation. Conclusion We have described a practical and convenient procedure for the synthesis of 1,3,5-triaryl-2-pyrazolines in sodium acetate-acetic acid aqueous solution at room temperature under ultrasound irradiation.

21 CFR 582.1005 - Acetic acid.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Acetic acid. 582.1005 Section 582.1005 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS....1005 Acetic acid. (a) Product. Acetic acid. (b) Conditions of use. This substance is generally...

Triacetin-based acetate supplementation as a chemotherapeutic adjuvant therapy in glioma.

Science.gov (United States)

Tsen, Andrew R; Long, Patrick M; Driscoll, Heather E; Davies, Matthew T; Teasdale, Benjamin A; Penar, Paul L; Pendlebury, William W; Spees, Jeffrey L; Lawler, Sean E; Viapiano, Mariano S; Jaworski, Diane M

2014-03-15

Cancer is associated with epigenetic (i.e., histone hypoacetylation) and metabolic (i.e., aerobic glycolysis) alterations. Levels of N-acetyl-L-aspartate (NAA), the primary storage form of acetate in the brain, and aspartoacylase (ASPA), the enzyme responsible for NAA catalysis to generate acetate, are reduced in glioma; yet, few studies have investigated acetate as a potential therapeutic agent. This preclinical study sought to test the efficacy of the food additive Triacetin (glyceryl triacetate, GTA) as a novel therapy to increase acetate bioavailability in glioma cells. The growth-inhibitory effects of GTA, compared to the histone deacetylase inhibitor Vorinostat (SAHA), were assessed in established human glioma cell lines (HOG and Hs683 oligodendroglioma, U87 and U251 glioblastoma) and primary tumor-derived glioma stem-like cells (GSCs), relative to an oligodendrocyte progenitor line (Oli-Neu), normal astrocytes, and neural stem cells (NSCs) in vitro. GTA was also tested as a chemotherapeutic adjuvant with temozolomide (TMZ) in orthotopically grafted GSCs. GTA-induced cytostatic growth arrest in vitro comparable to Vorinostat, but, unlike Vorinostat, GTA did not alter astrocyte growth and promoted NSC expansion. GTA alone increased survival of mice engrafted with glioblastoma GSCs and potentiated TMZ to extend survival longer than TMZ alone. GTA was most effective on GSCs with a mesenchymal cell phenotype. Given that GTA has been chronically administered safely to infants with Canavan disease, a leukodystrophy due to ASPA mutation, GTA-mediated acetate supplementation may provide a novel, safe chemotherapeutic adjuvant to reduce the growth of glioma tumors, most notably the more rapidly proliferating, glycolytic and hypoacetylated mesenchymal glioma tumors. © 2013 UICC.

Involvement of phorbol-12-myristate-13-acetate-induced protein 1 in goniothalamin-induced TP53-dependent and -independent apoptosis in hepatocellular carcinoma-derived cells

International Nuclear Information System (INIS)

Kuo, Kung-Kai; Chen, Yi-Ling; Chen, Lih-Ren; Li, Chien-Feng; Lan, Yu-Hsuan; Chang, Fang-Rong; Wu, Yang-Chang; Shiue, Yow-Ling

2011-01-01

The objective was to investigate the upstream apoptotic mechanisms that were triggered by a styrylpyrone derivative, goniothalamin (GTN), in tumor protein p53 (TP53)-positive and -negative hepatocellular carcinoma (HCC)-derived cells. Effects of GTN were evaluated by the flow cytometry, alkaline comet assay, immunocytochemistry, small-hairpin RNA interference, mitochondria/cytosol fractionation, quantitative reverse transcription-polymerase chain reaction, immunoblotting analysis and caspase 3 activity assays in two HCC-derived cell lines. Results indicated that GTN triggered phorbol-12-myristate-13-acetate-induced protein 1 (PMAIP1, also known as NOXA)-mediated apoptosis via TP53-dependent and -independent pathways. In TP53-positive SK-Hep1 cells, GTN furthermore induced TP53 transcription-dependent and -independent apoptosis. After GTN treatment, accumulation of reactive oxygen species, formation of DNA double-strand breaks, transactivation of TP53 and/or PMAIP1 gene, translocation of TP53 and/or PMAIP1 proteins to mitochondria, release of cytochrome c from mitochondria, cleavage of caspases and induction of apoptosis in both cell lines were sustained. GTN might represent a novel class of anticancer drug that induces apoptosis in HCC-derived cells through PMAIP1 transactivation regardless of the status of TP53 gene. - Highlights: → Goniothalamin (GTN) induced apoptosis in hepatocellular carcinomas-derived cells. → The apoptosis induced by GTN is PMAIP1-dependent, regardless of TP53 status. → The apoptosis induced by GTN might be TP53 transcription-dependent or -independent. → GTN-induced apoptosis is mitochondria- and caspases-mediated.

Simultaneous production of acetic and gluconic acids by a thermotolerant Acetobacter strain during acetous fermentation in a bioreactor.

Science.gov (United States)

Mounir, Majid; Shafiei, Rasoul; Zarmehrkhorshid, Raziyeh; Hamouda, Allal; Ismaili Alaoui, Mustapha; Thonart, Philippe

2016-02-01

The activity of bacterial strains significantly influences the quality and the taste of vinegar. Previous studies of acetic acid bacteria have primarily focused on the ability of bacterial strains to produce high amounts of acetic acid. However, few studies have examined the production of gluconic acid during acetous fermentation at high temperatures. The production of vinegar at high temperatures by two strains of acetic acid bacteria isolated from apple and cactus fruits, namely AF01 and CV01, respectively, was evaluated in this study. The simultaneous production of gluconic and acetic acids was also examined in this study. Biochemical and molecular identification based on a 16s rDNA sequence analysis confirmed that these strains can be classified as Acetobacter pasteurianus. To assess the ability of the isolated strains to grow and produce acetic acid and gluconic acid at high temperatures, a semi-continuous fermentation was performed in a 20-L bioreactor. The two strains abundantly grew at a high temperature (41°C). At the end of the fermentation, the AF01 and CV01 strains yielded acetic acid concentrations of 7.64% (w/v) and 10.08% (w/v), respectively. Interestingly, CV01 was able to simultaneously produce acetic and gluconic acids during acetic fermentation, whereas AF01 mainly produced acetic acid. In addition, CV01 was less sensitive to ethanol depletion during semi-continuous fermentation. Finally, the enzymatic study showed that the two strains exhibited high ADH and ALDH enzyme activity at 38°C compared with the mesophilic reference strain LMG 1632, which was significantly susceptible to thermal inactivation. Copyright © 2015 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

The cerebral metabolism of amino acids and related metabolites as studied by 13C and 14C labelling

International Nuclear Information System (INIS)

Hassel, B.

1995-11-01

The present investigations show the feasibility of analyzing the cerebral metabolism of amino acids and related metabolites by 13 C-and 14 C-labelling using labelled acetate and glucose as markers for glial and neuronal metabolism, respectively. Using [ 13 C[acetate, it was shown that glial cells export ∼60% of their TCA cycle intermediates, mostly as glutamine, and that this glutamine is used by neurons partly as an energy reserve, and partly it is converted directly to glutamate and GABA. Using [ 13 C[glucose, the glial process or pyruvate carboxylation was shown to compensate fully for the loss of glutamine. The mechanism of action of two neurotoxins, fluorocitrate and 3-nitropropionate was elucidated. The latter toxin was shown to inhibit the TCA cycle of GABAergic neurons selectively. Formation of pyruvate and lactate from glial TCA cycle intermediates was demonstrated in vivo. This pathway may be important for glial inactivation of transmitter glutamate and GABA. The results illustrate glianeuronal interactions, and they suggest the applicability of 13 CNMR spectroscopy to the detailed study of the cerebral metabolism of amino acids in the intact, unanesthetized human brain. 174 refs

Air-oxidized linalyl acetate - an emerging fragrance allergen?

Science.gov (United States)

Hagvall, Lina; Berglund, Victoria; Bråred Christensson, Johanna

2015-04-01

Linalyl acetate is a fragrance chemical that is prone to autoxidation. Exposure to linalyl acetate occurs through cosmetic products and essential oils, but is difficult to assess, as linalyl acetate is not labelled in the EU. To investigate the frequencies of contact allergy to oxidized linalyl acetate among dermatitis patients, and to investigate the autoxidation of linalyl acetate in terms of hydroperoxide formation and sensitization potency. Hydroperoxide formation in air-exposed linalyl acetate was determined with high-performance liquid chromatography. The sensitization potencies of hydroperoxides were determined with the local lymph node assay. One thousand seven hundred and seventeen patients were patch tested with oxidized linalyl acetate at 6.0% in petrolatum. Of the patients, 2.2% showed positive reactions to oxidized linalyl acetate. Forty-three per cent of the positive patients also had positive patch test reactions to other fragrance markers. Linalyl acetate hydroperoxides were detected early in the autoxidation process, and accumulated to a concentration of 37% after 42 weeks of air exposure. The linalyl acetate hydroperoxides were classified as moderate sensitizers. The frequency of positive reactions to oxidized linalyl acetate is comparable to that of previously studied oxidized fragrance terpenes. Oxidized linalyl acetate could thus be a common fragrance contact allergen. © 2015 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

The Cost-Effectiveness of Emergency Hormonal Contraception with Ulipristal Acetate versus Levonorgestrel for Minors in France.

Directory of Open Access Journals (Sweden)

Ramona Schmid

Full Text Available To evaluate the cost-effectiveness of ulipristal acetate and levonorgestrel in minors in France, and analyze whether it is worthwhile to provide ulipristal acetate to minors free of charge.The cost-effectiveness of two emergency contraceptive methods was compared based on a decision-analytical model. Pregnancy rates, outcomes of unintended pregnancies, and resource utilization were derived from the literature. Resources and their costs were considered until termination or a few days after delivery. Deterministic and probabilistic sensitivity analyses were performed.The cost of an unintended pregnancy in a French minor is estimated to be 1,630 € (range 1,330 € - 1,803 €. Almost 4 million € (3.1 € - 13.7 € million in unintended pregnancy spending in 2010 could have been saved by the use of ulipristal acetate instead of levonorgestrel. The incremental cost of ulipristal acetate compared to levonorgestrel is 3.30 € per intake, or 418 € per pregnancy avoided (intake within 72 hours. In the intake within 24 hours subgroup, ulipristal acetate was found to be more efficacious at a lower cost compared to levonorgestrel.Ulipristal acetate dominates levonorgestrel when taken within 24 hours after unprotected intercourse, i.e., it is more effective at a lower cost. When taken within 72 hours, ulipristal acetate is a cost- effective alternative to levonorgestrel, given that the cost of avoiding an additional pregnancy with ulipristal acetate is less than the average cost of these pregnancies. In the light of these findings, it is worthwhile to provide free access to minors.

Yeast Metabolites of Glycated Amino Acids in Beer.

Science.gov (United States)

Hellwig, Michael; Beer, Falco; Witte, Sophia; Henle, Thomas

2018-06-01

Glycation reactions (Maillard reactions) during the malting and brewing processes are important for the development of the characteristic color and flavor of beer. Recently, free and protein-bound Maillard reaction products (MRPs) such as pyrraline, formyline, and maltosine were found in beer. Furthermore, these amino acid derivatives are metabolized by Saccharomyces cerevisiae via the Ehrlich pathway. In this study, a method was developed for quantitation of individual Ehrlich intermediates derived from pyrraline, formyline, and maltosine. Following synthesis of the corresponding reference material, the MRP-derived new Ehrlich alcohols pyrralinol (up to 207 μg/L), formylinol (up to 50 μg/L), and maltosinol (up to 6.9 μg/L) were quantitated for the first time in commercial beer samples by reverse phase high performance liquid chromatography tandem mass spectrometry in the multiple reaction monitoring mode. This is equivalent to ca. 20-40% of the concentrations of the parent glycated amino acids. The metabolites were almost absent from alcohol-free beers and malt-based beverages. Two previously unknown valine-derived pyrrole derivatives were characterized and qualitatively identified in beer. The metabolites investigated represent new process-induced alkaloids that may influence brewing yeast performance due to structural similarities to quorum sensing and metal-binding molecules.

Measurement of δ13C values of soil amino acids by GC-C-IRMS using trimethylsilylation: a critical assessment.

Science.gov (United States)

Rubino, Mauro; Milin, Sylvie; D'Onofrio, Antonio; Signoret, Patrick; Hatté, Christine; Balesdent, Jérôme

2014-01-01

In this study, we evaluated trimethylsilyl (TMS) derivatives as derivatization reagents for the compound-specific stable carbon isotope analysis of soil amino acids by gas chromatography-combustion-isotope ratio mass spectrometry (GC-C-IRMS). We used non-proteinogenic amino acids to show that the extraction-derivatization-analysis procedure provides a reliable method to measure δ(13)C values of amino acids extracted from soil. However, we found a number of drawbacks that significantly increase the final total uncertainty. These include the following: production of multiple peaks for each amino acid, identified as di-, tri- and tetra-TMS derivatives; a number of TMS-carbon (TMS-C) atoms added lower than the stoichiometric one, possibly due to incomplete combustion; different TMS-C δ(13)C for di-, tri- and tetra-TMS derivatives. For soil samples, only four amino acids (leucine, valine, threonine and serine) provide reliable δ(13)C values with a total average uncertainty of 1.3 ‰. We conclude that trimethylsilyl derivatives are only suitable for determining the (13)C incorporation in amino acids within experiments using (13)C-labelled tracers but cannot be applied for amino acids with natural carbon isotope abundance until the drawbacks described here are overcome and the measured total uncertainty significantly decreased.

Analysis of amino acids by HPLC/electrospray negative ion tandem mass spectrometry using 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) derivatization.

Science.gov (United States)

Ziegler, Jörg; Abel, Steffen

2014-12-01

A new method for the determination of amino acids is presented. It combines established methods for the derivatization of primary and secondary amino groups with 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) with the subsequent amino acid specific detection of the derivatives by LC-ESI-MS/MS using multiple reaction monitoring (MRM). The derivatization proceeds within 5 min, and the resulting amino acid derivatives can be rapidly purified from matrix by solid-phase extraction (SPE) on HR-X resin and separated by reversed-phase HPLC. The Fmoc derivatives yield several amino acid specific fragment ions which opened the possibility to select amino acid specific MRM transitions. The method was applied to all 20 proteinogenic amino acids, and the quantification was performed using L-norvaline as standard. A limit of detection as low as 1 fmol/µl with a linear range of up to 125 pmol/µl could be obtained. Intraday and interday precisions were lower than 10 % relative standard deviations for most of the amino acids. Quantification using L-norvaline as internal standard gave very similar results compared to the quantification using deuterated amino acid as internal standards. Using this protocol, it was possible to record the amino acid profiles of only a single root from Arabidopsis thaliana seedlings and to compare it with the amino acid profiles of 20 dissected root meristems (200 μm).

Lipases and whole cell biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and its ester.

Science.gov (United States)

Majewska, Paulina; Serafin, Monika; Klimek-Ochab, Magdalena; Brzezińska-Rodak, Małgorzata; Żymańczyk-Duda, Ewa

2016-06-01

A wide spectrum of commercially available lipases and microbial whole cells catalysts were tested for biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid 1 and its butyryl ester. The best results were achieved for biocatalytic hydrolysis of ester: 2-butyryloxy-2-(ethoxyphenylphosphinyl)acetic acid 2 performed by lipase from Candida cylindracea, what gave optically active products with 85% enantiomeric excess, 50% conversion degree and enantioselectivity 32.9 for one pair of enantiomers. Also enzymatic systems of Penicillium minioluteum and Fusarium oxysporum were able to hydrolyze tested compound with high enantiomeric excess (68-93% ee), enantioselectivity (44 for one pair of enantiomers) and conversion degree about 50-55%. Enzymatic acylation of hydroxyphosphinate was successful in case when porcine pancreas lipase was used. After 4days of biotransformation the conversion reaches 45% but the enantiomeric enrichment of the isomers mixture do not exceed 43%. Obtained chiral compounds are valuable derivatizing agents for spectroscopic (NMR) evaluation of enantiomeric excess for particular compounds (e.g. amino acids). Copyright © 2016 The Authors. Published by Elsevier Inc. All rights reserved.

Distribution of stable free radicals among amino acids of isolated soy proteins.

Science.gov (United States)

Lei, Qingxin; Liebold, Christopher M; Boatright, William L; Shah Jahan, M

2010-09-01

Application of deuterium sulfide to powdered isolated soy proteins (ISP) was used to quench stable free radicals and produce a single deuterium label on amino acids where free radicals reside. The deuterium labels rendered increases of isotope ratio for the specific ions of radical-bearing amino acids. Isotope ratio measurements were achieved by gas chromatography/mass spectrometry (GC/MS) analyses after the amino acids were released by acidic hydrolysis and converted to volatile derivatives with propyl chloroformate. The isotope enrichment data showed the stable free radicals were located on Ala, Gly, Leu, Ile, Asx (Asp+Asn), Glx (Glu+Gln), and Trp but not on Val, Pro, Met, Phe, Lys, and His. Due to the low abundance of Ser, Thr, and Cys derivatives and the impossibility to accurately measure their isotope ratios, the radical bearing status for these amino acids remained undetermined even though their derivatives were positively identified from ISP hydrolysates. The relative isotope enrichment for radical-bearing amino acids Ala, Gly, Leu, Ile, Asx (Asp+Asn), Glx (Glu+Gln), and Trp were 8.67%, 2.96%, 2.90%, 3.94%, 6.03%, 3.91%, and 21.48%, respectively. Isotope ratio increase for Tyr was also observed but further investigation revealed such increase was mainly from nonspecific deuterium-hydrogen exchange not free radical quenching. The results obtained from the present study provide important information for a better understanding of the mechanisms of free radical formation and stabilization in "dry" ISP.

Lichenysin production is improved in codY null Bacillus licheniformis by addition of precursor amino acids.

Science.gov (United States)

Zhu, Chengjun; Xiao, Fang; Qiu, Yimin; Wang, Qin; He, Zhili; Chen, Shouwen

2017-08-01

Lichenysin is categorized into the family of lipopeptide biosurfactants and has a variety of applications in the petroleum industry, bioremediation, pharmaceuticals, and the food industry. Currently, large-scale production is limited due to the low yield. This study found that lichenysin production was repressed by supplementation of extracellular amino acids. The global transcriptional factor CodY was hypothesized to prevent lichenysin biosynthesis under an amino acid-rich condition in Bacillus licheniformis. Thus, the codY null strain was constructed, and lichenysin production was increased by 31.0% to 2356 mg/L with the addition of precursor amino acids, and the lichenysin production efficiency was improved by 42.8% to 98.2 mg/L• h. Correspondingly, the transcription levels of the lichenysin synthetase gene lchAA, and its corresponding regulator genes comA, degQ, and degU, were upregulated. Also, the codY deletion enhanced biosynthesis of lichenysin precursor amino acids (Gln, Ile, Leu, and Val) and reduced the formation of byproducts, acetate, acetoin, and 2,3-butanediol. This study firstly reported that lichenysin biosynthesis was negatively regulated by CodY and lichenysin production could be further improved with the precursor amino acid amendment in the codY null strain.

Simultaneous determination of triacetin, acetic ether, butyl acetate and amorolfine hydrochloride in amorolfine liniment by HPLC.

Science.gov (United States)

Gao, Yuan; Li, Li; Zhang, Jianjun; Shu, Wenjuan; Gao, Liqiong

2012-04-01

A simple, rapid, specific and precise reversed-phase high-performance liquid chromatographic method was developed for simultaneous estimation of triacetin, acetic ether, butyl acetate and amorolfine in marketed pharmaceutical liniment. Chromatographic separation was performed on a Shimadzu VP-ODS C(18) column using the mixture of citric acid-hydrochloric acid-sodium hydrate buffer (pH 3.0), acetonitrile and methanol (32:30:38) as the mobile phase at a flow rate of 1.0 mL/min with UV-detection at 215 nm. The method separated the four components simultaneously in less than 10 min. The validation of the method was performed with respect to specificity, linearity, accuracy, and precision. The calibration curves were linear in the range of 35.1-81.9 μ/mL for triacetin, 431.1-1005.9 μ/mL for acetic ether, 167.0-389.7 μ/mL for butyl acetate and 151.0-352.3 μ/mL for amorolfine. The mean 100% spiked recovery for triacetin, acetic ether, butyl acetate and amorolfine is 99.43 ± 0.42, 101.5 ± 1.09, 101.4 ± 1.02 and 100.8 ± 0.69, respectively. The intra-day and inter-day relative standard deviation values were liniment.

Indole-3-acetic acid biosynthesis in Fusarium delphinoides strain GPK, a causal agent of Wilt in Chickpea.

Science.gov (United States)

Kulkarni, Guruprasad B; Sanjeevkumar, S; Kirankumar, B; Santoshkumar, M; Karegoudar, T B

2013-02-01

Fusarium delphinoides (Ascomycota; Nectriaceae) is an indole-3-acetic acid (IAA) producing plant pathogen and a causal agent of wilt in chickpea. The IAA biosynthetic pathway in F. delphinoides strain GPK (FDG) was examined by analyzing metabolic intermediates and by feeding experiments. Gas chromatograph (GC) analysis of FDG culture filtrates showed the presence of metabolic intermediates of indole-3-pyruvic acid (IPyA), indole-3-acetamide (IAM), and tryptamine (TRA) pathways. The different IAA biosynthetic pathways were further confirmed by identifying the presence of different enzymes of these pathways. Substrate specificity study of aromatic amino acid aminotransferase revealed that the enzyme is highly specific for tryptophan (Trp) and α-ketoglutarate (α-kg) as amino group donor and acceptor, respectively. Furthermore, the concentration-dependent effect of exogenous IAA on fungal growth was established. Low concentration of exogenous IAA increases the fungal growth and at high concentration it decreases the growth of FDG.

VITAL NMR: using chemical shift derived secondary structure information for a limited set of amino acids to assess homology model accuracy

Energy Technology Data Exchange (ETDEWEB)

Brothers, Michael C.; Nesbitt, Anna E.; Hallock, Michael J. [University of Illinois at Urbana-Champaign, Department of Chemistry (United States); Rupasinghe, Sanjeewa G. [University of Illinois at Urbana-Champaign, Department of Cell and Developmental Biology (United States); Tang Ming [University of Illinois at Urbana-Champaign, Department of Chemistry (United States); Harris, Jason; Baudry, Jerome [University of Tennessee, Department of Biochemistry, Cellular and Molecular Biology (United States); Schuler, Mary A. [University of Illinois at Urbana-Champaign, Department of Cell and Developmental Biology (United States); Rienstra, Chad M., E-mail: rienstra@illinois.edu [University of Illinois at Urbana-Champaign, Department of Chemistry (United States)

2012-01-15

Homology modeling is a powerful tool for predicting protein structures, whose success depends on obtaining a reasonable alignment between a given structural template and the protein sequence being analyzed. In order to leverage greater predictive power for proteins with few structural templates, we have developed a method to rank homology models based upon their compliance to secondary structure derived from experimental solid-state NMR (SSNMR) data. Such data is obtainable in a rapid manner by simple SSNMR experiments (e.g., {sup 13}C-{sup 13}C 2D correlation spectra). To test our homology model scoring procedure for various amino acid labeling schemes, we generated a library of 7,474 homology models for 22 protein targets culled from the TALOS+/SPARTA+ training set of protein structures. Using subsets of amino acids that are plausibly assigned by SSNMR, we discovered that pairs of the residues Val, Ile, Thr, Ala and Leu (VITAL) emulate an ideal dataset where all residues are site specifically assigned. Scoring the models with a predicted VITAL site-specific dataset and calculating secondary structure with the Chemical Shift Index resulted in a Pearson correlation coefficient (-0.75) commensurate to the control (-0.77), where secondary structure was scored site specifically for all amino acids (ALL 20) using STRIDE. This method promises to accelerate structure procurement by SSNMR for proteins with unknown folds through guiding the selection of remotely homologous protein templates and assessing model quality.

VITAL NMR: Using Chemical Shift Derived Secondary Structure Information for a Limited Set of Amino Acids to Assess Homology Model Accuracy

Energy Technology Data Exchange (ETDEWEB)

Brothers, Michael C [University of Illinois, Urbana-Champaign; Nesbitt, Anna E [University of Illinois, Urbana-Champaign; Hallock, Michael J [University of Illinois, Urbana-Champaign; Rupasinghe, Sanjeewa [University of Illinois, Urbana-Champaign; Tang, Ming [University of Illinois, Urbana-Champaign; Harris, Jason B [ORNL; Baudry, Jerome Y [ORNL; Schuler, Mary A [University of Illinois, Urbana-Champaign; Rienstra, Chad M [University of Illinois, Urbana-Champaign

2011-01-01

Homology modeling is a powerful tool for predicting protein structures, whose success depends on obtaining a reasonable alignment between a given structural template and the protein sequence being analyzed. In order to leverage greater predictive power for proteins with few structural templates, we have developed a method to rank homology models based upon their compliance to secondary structure derived from experimental solid-state NMR (SSNMR) data. Such data is obtainable in a rapid manner by simple SSNMR experiments (e.g., (13)C-(13)C 2D correlation spectra). To test our homology model scoring procedure for various amino acid labeling schemes, we generated a library of 7,474 homology models for 22 protein targets culled from the TALOS+/SPARTA+ training set of protein structures. Using subsets of amino acids that are plausibly assigned by SSNMR, we discovered that pairs of the residues Val, Ile, Thr, Ala and Leu (VITAL) emulate an ideal dataset where all residues are site specifically assigned. Scoring the models with a predicted VITAL site-specific dataset and calculating secondary structure with the Chemical Shift Index resulted in a Pearson correlation coefficient (-0.75) commensurate to the control (-0.77), where secondary structure was scored site specifically for all amino acids (ALL 20) using STRIDE. This method promises to accelerate structure procurement by SSNMR for proteins with unknown folds through guiding the selection of remotely homologous protein templates and assessing model quality.

Mycosporine-Like Amino Acids and Their Derivatives as Natural Antioxidants

OpenAIRE

Naoki Wada; Toshio Sakamoto; Seiichi Matsugo

2015-01-01

Mycosporine-like amino acids (MAAs) are water-soluble molecules that absorb UV-A and UV-B radiation and disperse the energy as heat. MAAs show great diversity in their molecular structures, which exhibit a range of molecular weights spanning 188 to 1050 Daltons. MAAs are utilized in a wide variety of organisms including prokaryotes and eukaryotic micro-organisms that inhabit aquatic, terrestrial, and marine environments. These features suggest that MAAs are stable and fundamental molecules th...

Acetate metabolism in Methanothrix soehngenii

NARCIS (Netherlands)

Jetten, M.S.M.

1991-01-01

Acetate is quantitatively the most important intermediate in the anaerobic degradation of soluble organic matter. The conversion rate of acetate by methanogenic bacteria is proposed to be the rate limiting step in this degradation The study of acetoclastic methanogens, therefore is of

21 CFR 184.1005 - Acetic acid.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acetic acid. 184.1005 Section 184.1005 Food and... Substances Affirmed as GRAS § 184.1005 Acetic acid. (a) Acetic acid (C2H4O2, CAS Reg. No. 64-19-7) is known as ethanoic acid. It occurs naturally in plant and animal tissues. It is produced by fermentation of...

New Perspectives on Acetate and One-Carbon Metabolism in the Methanoarchaea

Energy Technology Data Exchange (ETDEWEB)

Ferry, James [Pennsylvania State Univ., University Park, PA (United States)

2017-03-20

Carbonic anhydrases catalyze the reversible hydration of carbon dioxide to bicarbonate. Although widespread in prokaryotes of the domains Bacteria and Archaea, few have been investigated and the physiological functions are largely unknown. Carbonic anhydrases are of biotechnological interest for carbon dioxide capture and sequestration at point sources. Prokaryotes encode three independently evolved classes. The alpha-class is restricted to a few pathogens and the other two are uniformly distributed in phylogenetically and physiologically diverse species. Although wide-spread in prokaryotes, only three gamma-class enzymes have been biochemically characterized and the physiological functions have not been investigated. The gamma-class is prominent in anaerobic acetate-utilizing methane-producing species of the genus Methanosarcina that encode three subclasses. Enzymes from two of the subclasses, Cam and CamH from Methanosarcina thermophila, have been characterized and found to utilize iron in the active site which is the first example of an iron-containing carbonic anhydrase. No representative of the third subclass has been isolated, although this subclass constitutes the great majority of the β-class. This grant application proposed to characterize gamma-class carbonic anhydrases from diverse anaerobic prokaryotes from the domains Bacteria and Archaea to broaden the understanding of this enzyme. In particular, the three subclasses present the genetically tractable acetate-utilizing methanogen Methanosarcina acetivorans will be investigated to extend studies of acetate and one-carbon metabolism in this species. A genetic approach will be taken to ascertain the physiological functions. It is also proposed to delve deeper into the mechanism of Cam from M. thermophila, the archetype of the gamma-class, via a high resolution neutron structure and kinetic analysis of site-specific amino acid replacement variants. In the course of the investigation, goals were added to

Measurement of the rates of oxindole-3-acetic acid turnover, and indole-3-acetic acid oxidation in Zea mays seedlings

Science.gov (United States)

Nonhebel, H. M.; Bandurski, R. S. (Principal Investigator)

1986-01-01

Oxindole-3-acetic acid is the principal catabolite of indole-3-acetic acid in Zea mays seedlings. In this paper measurements of the turnover of oxindole-3-acetic acid are presented and used to calculate the rate of indole-3-acetic acid oxidation. [3H]Oxindole-3-acetic acid was applied to the endosperm of Zea mays seedlings and allowed to equilibrate for 24 h before the start of the experiment. The subsequent decrease in its specific activity was used to calculate the turnover rate. The average half-life of oxindole-3-acetic acid in the shoots was found to be 30 h while that in the kernels had an average half-life of 35h. Using previously published values of the pool sizes of oxindole-3-acetic acid in shoots and kernels from seedlings of the same age and variety, and grown under the same conditions, the rate of indole-3-acetic acid oxidation was calculated to be 1.1 pmol plant-1 h-1 in the shoots and 7.1 pmol plant-1 h-1 in the kernels.

Density, dynamic viscosity, and derived properties of binary mixtures of methanol or ethanol with water, ethyl acetate, and methyl acetate at T (293.15, 298.15, and 303.15) K

Energy Technology Data Exchange (ETDEWEB)

Gonzalez, Begona; Calvar, Noelia; Gomez, Elena [Chemical Engineering Department, University of Vigo, 36200 Vigo (Spain); Dominguez, Angeles [Chemical Engineering Department, University of Vigo, 36200 Vigo (Spain)], E-mail: admguez@uvigo.es

2007-12-15

Densities and dynamic viscosities for methanol or ethanol with water, ethyl acetate, and methyl acetate at several temperatures T = (293.15, 298.15, and 303.15) K have been measured over the whole composition range and 0.1 MPa, along with the properties of the pure components. Excess molar volumes, viscosity deviations, and excess free energy of activation for the binary systems at the above-mentioned temperatures, were calculated and fitted to the Redlich-Kister equation to determine the fitting parameters and the root-mean-square deviations. UNIQUAC equation was used to correlate the experimental viscosity data. The UNIFAC-VISCO method and ASOG-VISCO method, based on contribution groups, were used to predict the dynamic viscosities of the binary mixtures.

Density, dynamic viscosity, and derived properties of binary mixtures of methanol or ethanol with water, ethyl acetate, and methyl acetate at T (293.15, 298.15, and 303.15) K

International Nuclear Information System (INIS)

Gonzalez, Begona; Calvar, Noelia; Gomez, Elena; Dominguez, Angeles

2007-01-01

Densities and dynamic viscosities for methanol or ethanol with water, ethyl acetate, and methyl acetate at several temperatures T = (293.15, 298.15, and 303.15) K have been measured over the whole composition range and 0.1 MPa, along with the properties of the pure components. Excess molar volumes, viscosity deviations, and excess free energy of activation for the binary systems at the above-mentioned temperatures, were calculated and fitted to the Redlich-Kister equation to determine the fitting parameters and the root-mean-square deviations. UNIQUAC equation was used to correlate the experimental viscosity data. The UNIFAC-VISCO method and ASOG-VISCO method, based on contribution groups, were used to predict the dynamic viscosities of the binary mixtures

Hyperpolarized Amino Acid Derivatives as Multivalent Magnetic Resonance pH Sensor Molecules

Directory of Open Access Journals (Sweden)

Christian Hundshammer

2018-02-01

Full Text Available pH is a tightly regulated physiological parameter that is often altered in diseased states like cancer. The development of biosensors that can be used to non-invasively image pH with hyperpolarized (HP magnetic resonance spectroscopic imaging has therefore recently gained tremendous interest. However, most of the known HP-sensors have only individually and not comprehensively been analyzed for their biocompatibility, their pH sensitivity under physiological conditions, and the effects of chemical derivatization on their logarithmic acid dissociation constant (pKa. Proteinogenic amino acids are biocompatible, can be hyperpolarized and have at least two pH sensitive moieties. However, they do not exhibit a pH sensitivity in the physiologically relevant pH range. Here, we developed a systematic approach to tailor the pKa of molecules using modifications of carbon chain length and derivatization rendering these molecules interesting for pH biosensing. Notably, we identified several derivatives such as [1-13C]serine amide and [1-13C]-2,3-diaminopropionic acid as novel pH sensors. They bear several spin-1/2 nuclei (13C, 15N, 31P with high sensitivity up to 4.8 ppm/pH and we show that 13C spins can be hyperpolarized with dissolution dynamic polarization (DNP. Our findings elucidate the molecular mechanisms of chemical shift pH sensors that might help to design tailored probes for specific pH in vivo imaging applications.

Hyperpolarized Amino Acid Derivatives as Multivalent Magnetic Resonance pH Sensor Molecules.

Science.gov (United States)

Hundshammer, Christian; Düwel, Stephan; Ruseckas, David; Topping, Geoffrey; Dzien, Piotr; Müller, Christoph; Feuerecker, Benedikt; Hövener, Jan B; Haase, Axel; Schwaiger, Markus; Glaser, Steffen J; Schilling, Franz

2018-02-15

pH is a tightly regulated physiological parameter that is often altered in diseased states like cancer. The development of biosensors that can be used to non-invasively image pH with hyperpolarized (HP) magnetic resonance spectroscopic imaging has therefore recently gained tremendous interest. However, most of the known HP-sensors have only individually and not comprehensively been analyzed for their biocompatibility, their pH sensitivity under physiological conditions, and the effects of chemical derivatization on their logarithmic acid dissociation constant (p K a ). Proteinogenic amino acids are biocompatible, can be hyperpolarized and have at least two pH sensitive moieties. However, they do not exhibit a pH sensitivity in the physiologically relevant pH range. Here, we developed a systematic approach to tailor the p K a of molecules using modifications of carbon chain length and derivatization rendering these molecules interesting for pH biosensing. Notably, we identified several derivatives such as [1- 13 C]serine amide and [1- 13 C]-2,3-diaminopropionic acid as novel pH sensors. They bear several spin-1/2 nuclei ( 13 C, 15 N, 31 P) with high sensitivity up to 4.8 ppm/pH and we show that 13 C spins can be hyperpolarized with dissolution dynamic polarization (DNP). Our findings elucidate the molecular mechanisms of chemical shift pH sensors that might help to design tailored probes for specific pH in vivo imaging applications.

Toxicity of copper chelates of azomethines and amino acids for Chlorella pyrenoidosa

Energy Technology Data Exchange (ETDEWEB)

Barashkov, G.K.; Rukhadze, E.G.; Talyzenkova, G.P.

1979-01-01

The authors have attempted to assess the toxicity of copper-containing compounds from the point of view of their interrelationship with the structural characteristics of the chelate compound and the structure of the ligand. The copper chelates of the azomethines tested may be provisionally divided into three types: A - complexes with N-alkly-azomethines; B - complexes with N-aryl-azomethines; C - binuclear complexes. Consideration was also given to chelates with aromatic and heterocyclic amino acids and to heteroligand chelates in which the copper atom coordinates azomethine and an amino acid simultaneously. Toxicity was determined by the method previously described and expressed as a critical concentration (C/sub cr/, mg Cu/liter) and in relative toxicity units (T/sub c/). The compounds investigated were obtained from the interaction between a bidentant ligand of an azomethine or anamino acid and copper acetate in a water-alcohol medium at pH 6-8. Since they are not very soluble in water, true solutions were obtained by using dimethyl sulfoxide.

Electrooxidation of activated alpha,omega-diols to cyclic tetramethylene acetals of the corresponding dials

Czech Academy of Sciences Publication Activity Database

Hlavatý, Jaromír; Polášek, Miroslav

2006-01-01

Roč. 47, č. 44 (2006), s. 7789-7791 ISSN 0040-4039 R&D Projects: GA ČR GA203/03/0825 Institutional research plan: CEZ:AV0Z40400503 Keywords : anodic oxidation * cyclic tetramethylene acetals * 2,7-dioxepyl derivatives Subject RIV: CG - Electrochemistry Impact factor: 2.509, year: 2006

Hydrolyses of alpha-naphthyl acetate, beta-naphthyl acetate, and acetyl-DL-phenylalanine beta-naphthyl ester

DEFF Research Database (Denmark)

Kirkeby, S; Moe, D

1983-01-01

Using simultaneous coupling azo dye techniques kidney enzymes active against alpha-naphthyl acetate, beta-naphthyl acetate, and acetyl-DL-phenylalanine beta-naphthyl ester are characterized. The enzymes show identical distribution in the section. The banding patterns in zymograms are the same after...

CLICK CHEMISTRY AS AN EFFICIENT TOOL TO ACCESS 6-AMINO-5-CYANO-2(1H)-PYRIMIDINONE DIMERS Klick-Chemie als effizientes Werkzeug ZUGREIFEN 6-Amino-5-cyano-2 (1H)-pyrimidinon Dimeren

OpenAIRE

Ennaji Najahi, Jan Sudor ,Françoise Nepveu, Fethi Zribi, Romain Duval and Fakher Chabchoub

2011-01-01

We describe here the synthesis of triazole-linked 6-amino-5-cyano-2(1H)-pyrimidinone dimers using 1,3-dipolar cycloaddition. The azido-precursor was prepared through the reaction of ethyl 2,2-dicyanovinylcarbamate derivatives with p-azidoaniline. The second precursor, a 6-amino-5- cyano-1-(3 or 4-ethynylphenyl)-4-substituted-2(1H)-pyrimidinone, was obtained from ethyl 2,2- dicyanovinylcarbamate derivatives reacting with 3-ethynylaniline or 4-ethynylaniline. Consequently, the two ‘click system...

Metabolomic analysis of alterations in lipid oxidation, carbohydrate and amino acid metabolism in dairy goats caused by exposure to Aflotoxin B1.

Science.gov (United States)

Cheng, Jianbo; Huang, Shuai; Fan, Caiyun; Zheng, Nan; Zhang, Yangdong; Li, Songli; Wang, Jiaqi

2017-11-01

The purposes of this study were to investigate the systemic and characteristic metabolites in the serum of dairy goats induced by aflatoxin B1 (AFB1) exposure and to further understand the endogenous metabolic alterations induced by it. A nuclear magnetic resonance (NMR)-based metabonomic approach was used to analyse the metabolic alterations in dairy goats that were induced by low doses of AFB1 (50 µg/kg DM). We found that AFB1 exposure caused significant elevations of glucose, citrate, acetate, acetoacetate, betaine, and glycine yet caused reductions of lactate, ketone bodies (acetate, β-hydroxybutyrate), amino acids (citrulline, leucine/isoleucine, valine, creatine) and cell membrane structures (choline, lipoprotein, N-acetyl glycoproteins) in the serum. These data indicated that AFB1 caused endogenous metabolic changes in various metabolic pathways, including cell membrane-associated metabolism, the tricarboxylic acid cycle, glycolysis, lipids, and amino acid metabolism. These findings provide both a comprehensive insight into the metabolic aspects of AFB1-induced adverse effects on dairy goats and a method for monitoring dairy animals exposed to low doses of AFB1.

Comparison of different amino acid derivatives and analysis of rat brain microdialysates by liquid chromatography tandem mass spectrometry.

Science.gov (United States)

Uutela, Päivi; Ketola, Raimo A; Piepponen, Petteri; Kostiainen, Risto

2009-02-09

The efficiencies of three derivatisation reagents that react with either the amine (9-fluorenylmethyl chloroformate (FMOC)) or the carboxylic acid group (butanol) of amino acid or with both types of functional groups (propyl chloroformate) were compared in the analysis of amino acids by liquid chromatography-electrospray-tandem mass spectrometry (LC-ESI-MS/MS). Separation of 20 amino acids derivatised with these three reagents was studied on reversed-phase chromatography. Linearity, repeatability and limits of detection of the LC-ESI-MS/MS method were determined by analysing FMOC-, butanol- and propyl chloroformate-derivatised lysine, beta-aminobutyric acid, threonine and glutamic acid. The limits of detection for the derivatised amino acids (7.5-75fmol) were as much as 2-60 times lower than those of the corresponding underivatised molecules. The best linearity was observed for amino acids derivatised with propyl chloroformate or butanol (r(2)=0.996-0.999, range=100-8500nmolL(-1)). Propyl chloroformate was the best suited of the reagents tested for the analysis of amino acids with LC-MS/MS and was used for the analysis of amino acids in rat brain microdialysis samples.

Chemical radiolabeling of carboxyatractyloside by [14C]acetic anhydride

International Nuclear Information System (INIS)

Block, M.R.; Pougeois, R.; Vignais, P.V.

1980-01-01

The authors report the synthesis and biological properties of a radiolabeled derivative of CAT obtained with acetylation of the primary alcohol of CAT with radiolabeled acetic anhydride. They also investigate the question of mutual exclusion of CAT and BA for binding to the mitochondrial ADP/ATP carrier in double labeling experiments based on the use of [ 3 H]BA and [ 14 C]Ac-CAT. The results are consistent with the view that the ADP/ATP carrier possesses two separate interacting binding sites for AT (or CAT) and for BA. (Auth.)

Evaluation Lactogenic Activity of Ethyl Acetate Fraction of Torbangun (Coleus amboinicus L.) Leaves

Science.gov (United States)

Damanik, R. M.; Kustiyah, L.; Hanafi, M.; Iwansyah, A. C.

2017-12-01

This study aimed to assess the lactogenic property of ethyl acetate fraction of torbangun (Coleus amboinicus L.) leaves and to identify the compounds that responsibility as ‘milk booster’ using LC- MS approach. Lactagogue activity was evaluated in terms of quantity of milk produced from the rats treated with commercial milk booster (AF), ethyl acetate fraction of torbangun leaves (EA), water extraction of torbangun (AQ) and kaempferol (KP). The feed was given orally every two days and starting from Day 2 after giving birth until Day 28. The performance of milk production was measured along the experimental period by weight-suckle-weight method. The level of prolactin serum was determined by ELISA methods. Histopathological analysis of mammary gland, liver, intestines and kidney tissues was carried out. Moreover, in order to profiling and identification of compounds of ethyl acetate fraction, ultra-performance liquid chromatography quadrupole time of flight to electrospray ionization mass spectrometry (UPLC-QTOF-ESI-MS) in the positive-ion mode was performed. The ethyl acetate fraction of torbangun leaves (EA) was induced milk production about 17%, and AF 22% and KP 51% compared to the control group. Meanwhile, the EA was not significantly stimulate the synthesis of serum prolactin at Day 14 and Day 28 (p>0.05). Administration of EA did not cause any signs or symptoms of toxicity. In addition, a total of ten compounds was identified by UPLC-QTOF-ESI/MS in the ethyl acetate fraction of the leaves of C. amboinicus, mostly phenolic compounds, flavonols and some of their glycoside derivatives, such as: digiprolatone, and kaempferol-3-7-O-di-rhamnopyranoside. The present study reveals the ethyl acetate fraction of torbangun leaves and its bioactive compounds has the potency as a remedy for stimulating and improving milk production.

MASS SPECTROMETRIC IDENTIFICATION OF AN AZOBENZENE DERIVATIVE PRODUCED BY SMECTITE-CATALYZED CONVERSION OF 3-AMINO-4-HYDROXPHENYLARSONIC ACID

Science.gov (United States)

We report here the first evidence of a possible mechanism for the formation of an azobenzene arsonic acid compound in the environment The compound was formed when 3-amino-4-hydroxyphenylarsonic acid (3-amino-HPAA) was added to aqueous suspensions of smectite clay The 3-amino-HPAA...

Oxidation of indole-3-acetic acid to oxindole-3-acetic acid by an enzyme preparation from Zea mays

Science.gov (United States)

Reinecke, D. M.; Bandurski, R. S.

1988-01-01

Indole-3-acetic acid is oxidized to oxindole-3-acetic acid by Zea mays tissue extracts. Shoot, root, and endosperm tissues have enzyme activities of 1 to 10 picomoles per hour per milligram protein. The enzyme is heat labile, is soluble, and requires oxygen for activity. Cofactors of mixed function oxygenase, peroxidase, and intermolecular dioxygenase are not stimulatory to enzymic activity. A heat-stable, detergent-extractable component from corn enhances enzyme activity 6- to 10-fold. This is the first demonstration of the in vitro enzymic oxidation of indole-3-acetic acid to oxindole-3-acetic acid in higher plants.

The cerebral metabolism of amino acids and related metabolites as studied by {sup 13}C and {sup 14}C labelling

Energy Technology Data Exchange (ETDEWEB)

Hassel, B

1995-11-01

The present investigations show the feasibility of analyzing the cerebral metabolism of amino acids and related metabolites by {sup 13}C-and {sup 14}C-labelling using labelled acetate and glucose as markers for glial and neuronal metabolism, respectively. Using [{sup 13}C]acetate, it was shown that glial cells export {approx}60% of their TCA cycle intermediates, mostly as glutamine, and that this glutamine is used by neurons partly as an energy reserve, and partly it is converted directly to glutamate and GABA. Using [{sup 13}C]glucose, the glial process or pyruvate carboxylation was shown to compensate fully for the loss of glutamine. The mechanism of action of two neurotoxins, fluorocitrate and 3-nitropropionate was elucidated. The latter toxin was shown to inhibit the TCA cycle of GABAergic neurons selectively. Formation of pyruvate and lactate from glial TCA cycle intermediates was demonstrated in vivo. This pathway may be important for glial inactivation of transmitter glutamate and GABA. The results illustrate glianeuronal interactions, and they suggest the applicability of {sup 13}CNMR spectroscopy to the detailed study of the cerebral metabolism of amino acids in the intact, unanesthetized human brain. 174 refs.

21 CFR 182.8892 - α-Tocopherol acetate.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true α-Tocopherol acetate. 182.8892 Section 182.8892 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD...-Tocopherol acetate. (a) Product. α-Tocopherol acetate. (b) Conditions of use. This substance is generally...

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

Directory of Open Access Journals (Sweden)

Tor E. Kristensen

2015-04-01

Full Text Available Amino acids, whether natural, semisynthetic or synthetic, are among the most important and useful chiral building blocks available for organic chemical synthesis. In principle, they can function as inexpensive, chiral and densely functionalized starting materials. On the other hand, the use of amino acid starting materials routinely necessitates protective group chemistry, and in reality, large-scale preparations of even the simplest side-chain derivatives of many amino acids often become annoyingly strenuous due to the necessity of employing protecting groups, on one or more of the amino acid functionalities, during the synthetic sequence. However, in the case of hydroxyamino acids such as hydroxyproline, serine, threonine, tyrosine and 3,4-dihydroxyphenylalanine (DOPA, many O-acyl side-chain derivatives are directly accessible via a particularly expedient and scalable method not commonly applied until recently. Direct acylation of unprotected hydroxyamino acids with acyl halides or carboxylic anhydrides under appropriately acidic reaction conditions renders possible chemoselective O-acylation, furnishing the corresponding side-chain esters directly, on multigram-scale, in a single step, and without chromatographic purification. Assuming a certain degree of stability under acidic reaction conditions, the method is also applicable for a number of related compounds, such as various amino alcohols and the thiol-functional amino acid cysteine. While the basic methodology underlying this approach has been known for decades, it has evolved through recent developments connected to amino acid-derived chiral organocatalysts to become a more widely recognized procedure for large-scale preparation of many useful side-chain derivatives of hydroxyamino acids and related compounds. Such derivatives are useful in peptide chemistry and drug development, as amino acid amphiphiles for asymmetric catalysis, and as amino acid acrylic precursors for preparation of

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

Science.gov (United States)

2015-01-01

Summary Amino acids, whether natural, semisynthetic or synthetic, are among the most important and useful chiral building blocks available for organic chemical synthesis. In principle, they can function as inexpensive, chiral and densely functionalized starting materials. On the other hand, the use of amino acid starting materials routinely necessitates protective group chemistry, and in reality, large-scale preparations of even the simplest side-chain derivatives of many amino acids often become annoyingly strenuous due to the necessity of employing protecting groups, on one or more of the amino acid functionalities, during the synthetic sequence. However, in the case of hydroxyamino acids such as hydroxyproline, serine, threonine, tyrosine and 3,4-dihydroxyphenylalanine (DOPA), many O-acyl side-chain derivatives are directly accessible via a particularly expedient and scalable method not commonly applied until recently. Direct acylation of unprotected hydroxyamino acids with acyl halides or carboxylic anhydrides under appropriately acidic reaction conditions renders possible chemoselective O-acylation, furnishing the corresponding side-chain esters directly, on multigram-scale, in a single step, and without chromatographic purification. Assuming a certain degree of stability under acidic reaction conditions, the method is also applicable for a number of related compounds, such as various amino alcohols and the thiol-functional amino acid cysteine. While the basic methodology underlying this approach has been known for decades, it has evolved through recent developments connected to amino acid-derived chiral organocatalysts to become a more widely recognized procedure for large-scale preparation of many useful side-chain derivatives of hydroxyamino acids and related compounds. Such derivatives are useful in peptide chemistry and drug development, as amino acid amphiphiles for asymmetric catalysis, and as amino acid acrylic precursors for preparation of

Metabolomic analysis reveals key metabolites related to the rapid adaptation of Saccharomyce cerevisiae to multiple inhibitors of furfural, acetic acid, and phenol.

Science.gov (United States)

Wang, Xin; Li, Bing-Zhi; Ding, Ming-Zhu; Zhang, Wei-Wen; Yuan, Ying-Jin

2013-03-01

During hydrolysis of lignocellulosic biomass, a broad range of inhibitors are generated, which interfere with yeast growth and bioethanol production. In order to improve the strain tolerance to multiple inhibitors--acetic acid, furfural, and phenol (three representative lignocellulose-derived inhibitors) and uncover the underlying tolerant mechanism, an adaptation experiment was performed in which the industrial Saccharomyces cerevisiae was cultivated repeatedly in a medium containing multiple inhibitors. The adaptation occurred quickly, accompanied with distinct increase in growth rate, glucose utilization rate, furfural metabolism rate, and ethanol yield, only after the first transfer. A similar rapid adaptation was also observed for the lab strains of BY4742 and BY4743. The metabolomic analysis was employed to investigate the responses of the industrial S. cereviaise to three inhibitors during the adaptation. The results showed that higher levels of 2-furoic acid, 2, 3-butanediol, intermediates in glycolytic pathway, and amino acids derived from glycolysis, were discovered in the adapted strains, suggesting that enhanced metabolic activity in these pathways may relate to resistance against inhibitors. Additionally, through single-gene knockouts, several genes related to alanine metabolism, GABA shunt, and glycerol metabolism were verified to be crucial for the resistance to multiple inhibitors. This study provides new insights into the tolerance mechanism against multiple inhibitors, and guides for the improvement of tolerant ethanologenic yeast strains for lignocellulose-bioethanol fermentation.

Glatiramer Acetate-associated Refractory Immune Thrombocytopenic Purpura

Directory of Open Access Journals (Sweden)

Iftach Sagy

2016-04-01

Full Text Available We present a case of glatiramer acetate-associated refractory immune thrombocytopenic purpura (ITP in a female patient with multiple sclerosis. A search of MEDLINE/PubMed did not find any connection between glatiramer acetate and thrombocytopenia, specifically ITP. The autoimmune reaction was resistant to conservative ITP treatment, and was eventually managed only by splenectomy. To the best of our knowledge, this is the first report of glatiramer acetate-associated ITP. Physicians should be aware of this condition, and consider performing routine blood counts at the beginning of glatiramer acetate treatment.

Vapour pressures and vapour-liquid equilibria of propyl acetate and isobutyl acetate with ethanol or 2-propanol at 0.15 MPa. Binary systems

Directory of Open Access Journals (Sweden)

Susial Pedro

2012-01-01

Full Text Available Vapour pressures of propyl acetate, isobutyl acetate and 2-propanol from 0.004 to 1.6 MPa absolute pressure and VLE data for the binary systems propyl acetate+ethanol, propyl acetate+2-propanol, isobutyl acetate+ethanol and isobutyl acetate+2-propanol at 0.15 MPa have been determined. The experimental VLE data were verified with the test of van Ness and the Fredenslund criterion. The propyl acetate+ethanol or +2-propanol binary systems have an azeotropic point at 0.15 MPa. The different versions of the UNIFAC and ASOG group contribution models were applied.

21 CFR 582.5892 - a-Tocopherol acetate.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 6 2010-04-01 2010-04-01 false a-Tocopherol acetate. 582.5892 Section 582.5892 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL... Supplements 1 § 582.5892 a-Tocopherol acetate. (a) Product. a-Tocopherol acetate. (b) Conditions of use. This...

Hydration of amino acids: FTIR spectra and molecular dynamics studies.

Science.gov (United States)

Panuszko, Aneta; Adamczak, Beata; Czub, Jacek; Gojło, Emilia; Stangret, Janusz

2015-11-01

The hydration of selected amino acids, alanine, glycine, proline, valine, isoleucine and phenylalanine, has been studied in aqueous solutions by means of FTIR spectra of HDO isotopically diluted in H2O. The difference spectra procedure and the chemometric method have been applied to remove the contribution of bulk water and thus to separate the spectra of solute-affected HDO. To support interpretation of obtained spectral results, molecular dynamics simulations of amino acids were performed. The structural-energetic characteristic of these solute-affected water molecules shows that, on average, water affected by amino acids forms stronger and shorter H-bonds than those in pure water. Differences in the influence of amino acids on water structure have been noticed. The effect of the hydrophobic side chain of an amino acid on the solvent interactions seems to be enhanced because of the specific cooperative coupling of water strong H-bond chain, connecting the carboxyl and amino groups, with the clathrate-like H-bond network surrounding the hydrocarbon side chain. The parameter derived from the spectral data, which corresponds to the contributions of the population of weak hydrogen bonds of water molecules which have been substituted by the stronger ones in the hydration sphere of amino acids, correlated well with the amino acid hydrophobicity indexes.

Impact of primary amine group from aminophospholipids and amino acids on marine phospholipids stability: Non-enzymatic browning and lipid oxidation

DEFF Research Database (Denmark)

Lu, Henna Fung Sieng; Nielsen, Nina Skall; Baron, Caroline P.

2013-01-01

The main objective of this study was to investigate the oxidative stability and non-enzymatic browning reactions of marine PL in the presence or in the absence of primary amine group from aminophospholipids and amino acids. Marine phospholipids liposomal dispersions were prepared from two authentic......) Strecker derived volatiles, (ii) yellowness index (YI), (iii) hydrophobic and (iv) hydrophilic pyrroles content. The oxidative stability of the samples was assessed through measurement of secondary lipid derived volatile oxidation products. The result showed that the presence of PE and amino acids caused...... the formation of pyrroles, generated Strecker derived volatiles, decreased the YI development and lowered lipid oxidation. The lower degree of lipid oxidation in liposomal dispersions containing amino acids might be attributed to antioxidative properties of pyrroles or amino acids....

Antibiofilm Properties of Acetic Acid

DEFF Research Database (Denmark)

Bjarnsholt, Thomas; Alhede, Morten; Jensen, Peter Østrup

2014-01-01

Bacterial biofilms are known to be extremely tolerant toward antibiotics and other antimicrobial agents. These biofilms cause the persistence of chronic infections. Since antibiotics rarely resolve these infections, the only effective treatment of chronic infections is surgical removal of the inf......Bacterial biofilms are known to be extremely tolerant toward antibiotics and other antimicrobial agents. These biofilms cause the persistence of chronic infections. Since antibiotics rarely resolve these infections, the only effective treatment of chronic infections is surgical removal...... of the infected implant, tissue, or organ and thereby the biofilm. Acetic acid is known for its antimicrobial effect on bacteria in general, but has never been thoroughly tested for its efficacy against bacterial biofilms. In this article, we describe complete eradication of both Gram-positive and Gram......-negative biofilms using acetic acid both as a liquid and as a dry salt. In addition, we present our clinical experience of acetic acid treatment of chronic wounds. In conclusion, we here present the first comprehensive in vitro and in vivo testing of acetic acid against bacterial biofilms....

Amino Acids Are an Ineffective Fertilizer for Dunaliella spp. Growth

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Colin A. Murphree

2017-05-01

Full Text Available Autotrophic microalgae are a promising bioproducts platform. However, the fundamental requirements these organisms have for nitrogen fertilizer severely limit the impact and scale of their cultivation. As an alternative to inorganic fertilizers, we investigated the possibility of using amino acids from deconstructed biomass as a nitrogen source in the genus Dunaliella. We found that only four amino acids (glutamine, histidine, cysteine, and tryptophan rescue Dunaliella spp. growth in nitrogen depleted media, and that supplementation of these amino acids altered the metabolic profile of Dunaliella cells. Our investigations revealed that histidine is transported across the cell membrane, and that glutamine and cysteine are not transported. Rather, glutamine, cysteine, and tryptophan are degraded in solution by a set of oxidative chemical reactions, releasing ammonium that in turn supports growth. Utilization of biomass-derived amino acids is therefore not a suitable option unless additional amino acid nitrogen uptake is enabled through genetic modifications of these algae.

Image-derived input function in dynamic human PET/CT: methodology and validation with 11C-acetate and 18F-fluorothioheptadecanoic acid in muscle and 18F-fluorodeoxyglucose in brain

International Nuclear Information System (INIS)

Croteau, Etienne; Lavallee, Eric; Hubert, Laurent; Rousseau, Jacques A.; Lecomte, Roger; Labbe, Sebastien M.; Carpentier, Andre C.; Pifferi, Fabien; Cunnane, Stephen C.; Benard, Francois

2010-01-01

Despite current advances in PET/CT systems, blood sampling still remains the standard method to obtain the radiotracer input function for tracer kinetic modelling. The purpose of this study was to validate the use of image-derived input functions (IDIF) of the carotid and femoral arteries to measure the arterial input function (AIF) in PET imaging. The data were obtained from two different research studies, one using 18 F-FDG for brain imaging and the other using 11 C-acetate and 18 F-fluoro-6-thioheptadecanoic acid ( 18 F-FTHA) in femoral muscles. The method was validated with two phantom systems. First, a static phantom consisting of syringes of different diameters containing radioactivity was used to determine the recovery coefficient (RC) and spill-in factors. Second, a dynamic phantom built to model bolus injection and clearance of tracers was used to establish the correlation between blood sampling, AIF and IDIF. The RC was then applied to the femoral artery data from PET imaging studies with 11 C-acetate and 18 F-FTHA and to carotid artery data from brain imaging with 18 F-FDG. These IDIF data were then compared to actual AIFs from patients. With 11 C-acetate, the perfusion index in the femoral muscle was 0.34±0.18 min -1 when estimated from the actual time-activity blood curve, 0.29±0.15 min -1 when estimated from the corrected IDIF, and 0.66±0.41 min -1 when the IDIF data were not corrected for RC. A one-way repeated measures (ANOVA) and Tukey's test showed a statistically significant difference for the IDIF not corrected for RC (p 18 F-FTHA there was a strong correlation between Patlak slopes, the plasma to tissue transfer rate calculated using the true plasma radioactivity content and the corrected IDIF for the femoral muscles (vastus lateralis r=0.86, p=0.027; biceps femoris r=0.90, p=0.017). On the other hand, there was no correlation between the values derived using the AIF and those derived using the uncorrected IDIF. Finally, in the brain imaging

Mechanisms leading to oligomers and SOA through aqueous photooxidation: insights from OH radical oxidation of acetic acid and methylglyoxal

Directory of Open Access Journals (Sweden)

Y. Tan

2012-01-01

Full Text Available Previous experiments have demonstrated that the aqueous OH radical oxidation of methylglyoxal produces low volatility products including pyruvate, oxalate and oligomers. These products are found predominantly in the particle phase in the atmosphere, suggesting that methylglyoxal is a precursor of secondary organic aerosol (SOA. Acetic acid plays a central role in the aqueous oxidation of methylglyoxal and it is a ubiquitous product of gas phase photochemistry, making it a potential "aqueous" SOA precursor in its own right. However, the fate of acetic acid upon aqueous-phase oxidation is not well understood. In this research, acetic acid (20 μM–10 mM was oxidized by OH radicals, and pyruvic acid and methylglyoxal experimental samples were analyzed using new analytical methods, in order to better understand the formation of SOA from acetic acid and methylglyoxal. Glyoxylic, glycolic, and oxalic acids formed from acetic acid and OH radicals. In contrast to the aqueous OH radical oxidation of methylglyoxal, the aqueous OH radical oxidation of acetic acid did not produce succinic acid and oligomers. This suggests that the methylgloxal-derived oligomers do not form through the acid catalyzed esterification pathway proposed previously. Using results from these experiments, radical mechanisms responsible for oligomer formation from methylglyoxal oxidation in clouds and wet aerosols are proposed. The importance of acetic acid/acetate as an SOA precursor is also discussed. We hypothesize that this and similar chemistry is central to the daytime formation of oligomers in wet aerosols.

Photoligation of self-assembled DNA constructs containing anthracene-functionalized 2'-amino-LNA monomers

DEFF Research Database (Denmark)

Pasternak, Karol; Pasternak, Anna; Gupta, Pankaj

2011-01-01

Efficient synthesis of a novel anthracene-functionalized 2'-amino-LNA phosphoramidite derivative is described together with its incorporation into oligodeoxynucleotides. Two DNA strands with the novel 2'-N-anthracenylmethyl-2'-amino-LNA monomers can be effectively cross-linked by photoligation...... at 366nm in various types of DNA constructs. Successful application of three differently functionalized 2'-amino-LNA monomers in self-assembled higher ordered structures for simultaneous cross-linking and monitoring of assembly formation is furthermore demonstrated....

Distribution of indole-3-acetic acid in Petunia hybrida shoot tip cuttings and relationship between auxin transport, carbohydrate metabolism and adventitious root formation.

OpenAIRE

Ahkami, Amir H.; Melzer, Michael; Ghaffari, Mohammad R.; Pollmann, Stephan; Ghorbani, Majid; Shahinnia, Fahimeh; Hajirezaei, Mohammad R.; Druege, Uwe

2013-01-01

To determine the contribution of polar auxin transport (PAT) to auxin accumulation and to adventitious root (AR) formation in the stem base of Petunia hybrida shoot tip cuttings, the level of indole-3-acetic acid (IAA) was monitored in non-treated cuttings and cuttings treated with the auxin transport blocker naphthylphthalamic acid (NPA) and was complemented with precise anatomical studies. The temporal course of carbohydrates, amino acids and activities of controlling enzymes was also inves...

Comparative metabolism of branched-chain amino acids to precursors of juvenile hormone biogenesis in corpora allata of lepidopterous versus nonlepidopterous insects

Energy Technology Data Exchange (ETDEWEB)

Brindle, P.A.; Schooley, D.A.; Tsai, L.W.; Baker, F.C.

1988-08-05

Comparative studies were performed on the role of branched-chain amino acids (BCAA) in juvenile hormone (JH) biosynthesis using several lepidopterous and nonlepidopterous insects. Corpora cardiaca-corpora allata complexes (CC-CA, the corpora allata being the organ of JH biogenesis) were maintained in culture medium containing a uniformly /sup 14/C-labeled BCAA, together with (methyl-/sup 3/H)methionine as mass marker for JH quantification. BCAA catabolism was quantified by directly analyzing the medium for the presence of /sup 14/C-labeled propionate and/or acetate, while JHs were extracted, purified by liquid chromatography, and subjected to double-label liquid scintillation counting. Our results indicate that active BCAA catabolism occurs within the CC-CA of lepidopterans, and this efficiently provides propionyl-CoA (from isoleucine or valine) for the biosynthesis of the ethyl branches of JH I and II. Acetyl-CoA, formed from isoleucine or leucine catabolism, is also utilized by lepidopteran CC-CA for biosynthesizing JH III and the acetate-derived portions of the ethyl-branched JHs. In contrast, CC-CA of nonlepidopterans fail to catabolize BCAA. Consequently, exogenous isoleucine or leucine does not serve as a carbon source for the biosynthesis of JH III by these glands, and no propionyl-CoA is produced for genesis of ethyl-branched JHs. This is the first observation of a tissue-specific metabolic difference which in part explains why these novel homosesquiterpenoids exist in lepidopterans, but not in nonlepidopterans.

Comparative metabolism of branched-chain amino acids to precursors of juvenile hormone biogenesis in corpora allata of lepidopterous versus nonlepidopterous insects

International Nuclear Information System (INIS)

Brindle, P.A.; Schooley, D.A.; Tsai, L.W.; Baker, F.C.

1988-01-01

Comparative studies were performed on the role of branched-chain amino acids (BCAA) in juvenile hormone (JH) biosynthesis using several lepidopterous and nonlepidopterous insects. Corpora cardiaca-corpora allata complexes (CC-CA, the corpora allata being the organ of JH biogenesis) were maintained in culture medium containing a uniformly 14 C-labeled BCAA, together with [methyl- 3 H]methionine as mass marker for JH quantification. BCAA catabolism was quantified by directly analyzing the medium for the presence of 14 C-labeled propionate and/or acetate, while JHs were extracted, purified by liquid chromatography, and subjected to double-label liquid scintillation counting. Our results indicate that active BCAA catabolism occurs within the CC-CA of lepidopterans, and this efficiently provides propionyl-CoA (from isoleucine or valine) for the biosynthesis of the ethyl branches of JH I and II. Acetyl-CoA, formed from isoleucine or leucine catabolism, is also utilized by lepidopteran CC-CA for biosynthesizing JH III and the acetate-derived portions of the ethyl-branched JHs. In contrast, CC-CA of nonlepidopterans fail to catabolize BCAA. Consequently, exogenous isoleucine or leucine does not serve as a carbon source for the biosynthesis of JH III by these glands, and no propionyl-CoA is produced for genesis of ethyl-branched JHs. This is the first observation of a tissue-specific metabolic difference which in part explains why these novel homosesquiterpenoids exist in lepidopterans, but not in nonlepidopterans

Study of Physical Properties for Sodium acetate with Water and Water - Acetone mixtures at Different Temperatures

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Ahmed Mohammed Abbas

2017-02-01

Full Text Available In this study binary and ternary solutions are prepared by using the sodium acetate concentrations (0.1, 0.125, 0.2, 0.25, 0.4, 0.5, 0.8, 1 M in water and acetone –water mixtures .The important parameters such as apparent molal volume, the partial molal volume transfer,  apparent  molal compressibility, free energy of activation of viscous flow and thermodynamic activation parameter (enthalpy and entropy determined of sodium acetate in water , 20%, 40% ,60% and 80% V/V acetone –water mixtures at 298.15K, 303.15K, and 308.15K from density and viscosity measurements espectively. The limiting apparent molal volumes and experimental slopes were derived from the Masson equation, have been interpreted in terms of solute–solvent and solute–solute interactions  respectively. The viscosity data were analyzed using theJones–Dole equation and the derived parameter B - coefficient has also been interpreted in terms of solute–solvent interactions in the solutions.

Nano Cu interaction with single amino acid tyrosine derived self-assemblies; study through XRD, AFM, confocal Raman microscopy, SERS and DFT methods

Science.gov (United States)

Govindhan, Raman; Karthikeyan, Balakrishnan

2017-12-01

3,5-Bis(trifluoromethyl)benzylamine derivatives of single amino acid tyrosine produced self-assembled nanotubes (BTTNTs) as simple Phe-Phe. It has been observed that tyrosine derivative gives exclusively micro and nano tubes irrespective of the concentration of the precursor monomer. However, the introduced xenobiotic trifluoromethyl group (TFM) present in key backbone positionsof the self assembly gives the specific therapeutic function has been highlighted. Herein this work study of such self assembled nanotubes were studied through experimental and theoretical methods. The interaction of nanocopper cluster with the nanotubes (Cu@BTTNTs) were extensively studied by various methods like XRD, AFM, confocal Raman microscopy, SERS and theoretical methods like Mulliken's atomic charge analysis. SERS reveals that the interactions of Cu cluster with NH2, OH, NH and phenyl ring π-electrons system of BTTNTs. DFT studies gave the total dipole moment values of Cu@BTTNTs and explained the nature of interaction.

Methodical investigation of the protein metabolism and of the bioenergetics of the protein retention in growing animals. 2

International Nuclear Information System (INIS)

Voelker, T.; Krawielitzki, K.; Klein, M.; Keller, J.

1983-01-01

The amino acid composition of the proteins in selected body fractions of chickens and the 15 N -excess of amino acids isolated from them resulting from a feeding experiment with long-term 15 NH 4 -acetate labelling were determined. The amino acid spectra of feathers, breast and leg muscles are characterized by differences in the content of individual amino acids specific for the organs, the composition of the proteins, however, is independent of the protein content of the ration and the age of the animals. The sarcoplasmatic and myofibrillar proteins also have typical amino acid patterns, which-with the exception of the histidine content-are neither influenced by the extraction of the proteins from the breast or leg muscles nor by the energy level of the feeding or the age of the animals. There are no significant differences in the metabolization of the main protein fraction of the breast and leg muscles. The oral supply of 15 N-ammonium acetate to broilers predominantly labels the non-essential amino acids so that the derived kinetic data chiefly represent the metabolism of the non-essential amino acids. (author)

Approaches to α-amino acids via rearrangement to electron-deficient nitrogen: Beckmann and Hofmann rearrangements of appropriate carboxyl-protected substrates

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Sosale Chandrasekhar

2012-08-01

Full Text Available The titled approaches were effected with various 2-substituted benzoylacetic acid oximes 3 (Beckmann and 2-substituted malonamic acids 9 (Hofmann, their carboxyl groups being masked as a 2,4,10-trioxaadamantane unit (an orthoacetate. The oxime mesylates have been rearranged with basic Al2O3 in refluxing CHCl3, and the malonamic acids with phenyliodoso acetate and KOH/MeOH. Both routes are characterized by excellent overall yields. Structure confirmation of final products was conducted with X-ray diffraction in selected cases. The final N-benzoyl and N-(methoxycarbonyl products are α-amino acids with both carboxyl and amino protection; hence, they are of great interest in peptide synthesis.

Structure-Activity Relationship Study of Sesquiterpene Lactones and Their Semi-Synthetic Amino Derivatives as Potential Antitrypanosomal Products

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Stefanie Zimmermann

2014-03-01

Full Text Available Sesquiterpene lactones (STLs are natural products that have potent antitrypanosomal activity in vitro and, in the case of cynaropicrin, also reduce parasitemia in the murine model of trypanosomiasis. To explore their structure-antitrypanosomal activity relationships, a set of 34 natural and semi-synthetic STLs and amino-STLs was tested in vitro against T. b. rhodesiense (which causes East African sleeping sickness and mammalian cancer cells (rat bone myoblast L6 cells. It was found that the α-methylene-γ-lactone moiety is necessary for both antitrypanosomal effects and cytotoxicity. Antitrypanosomal selectivity is facilitated by 2-(hydroxymethylacrylate or 3,4-dihydroxy-2-methylenebutylate side chains, and by the presence of cyclopentenone rings. Semi-synthetic STL amines with morpholino and dimethylamino groups showed improved in vitro activity over the native STLs. The dimethylamino derivative of cynaropicrin was prepared and tested orally in the T. b. rhodesiense acute mouse model, where it showed reduced toxicity over cynaropicrin, but also lost antitrypanosomal activity.

Synthesis and anticancer evaluation of imidazolinone and benzoxazole derivatives

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Heba A. El-Hady

2017-05-01

Full Text Available A series of imidazolinone and benzoxazole derivatives (3 and 5 have been synthesized by the condensation of oxazolinone derivatives (2a–c with aniline and 2-hydroxyaniline. Acetyl derivatives (4, 6 and 7 were prepared via acetylation of compounds 3 and 5 with acetic anhydride and chloroacetyl chloride. The results revealed that imidazolinone and benzoxazole derivatives are potent against the cancer cell lines MCF-7 and HePG2. In particular, benzoxazole derivatives are more potent than imidazolinone derivatives.

Proton conductivity and relaxation properties of chitosan-acetate films

International Nuclear Information System (INIS)

Prokhorov, E.; Luna-Bárcenas, G.; González-Campos, J.B.; Kovalenko, Yu.; García-Carvajal, Z.Y.; Mota-Morales, J.

2016-01-01

Graphical abstract: Temperature dependence of conductivity, the number of density and proton mobility in chitosan-acetate film. - Highlights: • DD, conductivity, Vogel temperature dependent on the concentration of acetic acid. • Proton conductivity of CS-acetate films interpreted using two Grotthuss mechanisms. • Transformation between two mechanisms observed at the glass transition temperature. - Abstract: The effect of aqueous acetic acid solution concentration during the preparation of chitosan-acetate (CS-acetate) films on the conductivity and relaxation properties were studied by dielectric and FTIR spectroscopies, TGA measurements and X-Ray diffraction. Analyses of the experimental results on the degree of deacetylation, water absorption, conductivity, Vogel temperature and activation energy demonstrate a strong dependence of these parameters on the concentration of the acid acetic solutions from which the films have been obtained. The proton conductivity and relaxation properties of CS-acetate films have been interpreted using two Grotthuss “structural diffusion” and “pack-acid” mechanisms. The transformation between these two mechanisms observed at temperature higher than CS-acetate glass transition temperature is due to an increase in the thermal motion of CS chains, water evaporation, hydrogen bond between water molecules and side groups of CS breaking and formation of new bonds between NH 3 + and acetate ions. Additionally, application of the Rice and Roth model allowed estimating the temperature dependence of proton number and their mobility in CS-acetate films. A systematic interpretation on the appropriate conductivity mechanism will help trigger the design of smart materials used in flexible electronic, solid polymer electrolytes for fuel cells and solid polymer batteries based on CS-acetate films.

Omics analysis of acetic acid tolerance in Saccharomyces cerevisiae.

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Geng, Peng; Zhang, Liang; Shi, Gui Yang

2017-05-01

Acetic acid is an inhibitor in industrial processes such as wine making and bioethanol production from cellulosic hydrolysate. It causes energy depletion, inhibition of metabolic enzyme activity, growth arrest and ethanol productivity losses in Saccharomyces cerevisiae. Therefore, understanding the mechanisms of the yeast responses to acetic acid stress is essential for improving acetic acid tolerance and ethanol production. Although 329 genes associated with acetic acid tolerance have been identified in the Saccharomyces genome and included in the database ( http://www.yeastgenome.org/observable/resistance_to_acetic_acid/overview ), the cellular mechanistic responses to acetic acid remain unclear in this organism. Post-genomic approaches such as transcriptomics, proteomics, metabolomics and chemogenomics are being applied to yeast and are providing insight into the mechanisms and interactions of genes, proteins and other components that together determine complex quantitative phenotypic traits such as acetic acid tolerance. This review focuses on these omics approaches in the response to acetic acid in S. cerevisiae. Additionally, several novel strains with improved acetic acid tolerance have been engineered by modifying key genes, and the application of these strains and recently acquired knowledge to industrial processes is also discussed.

Prebiotic Amino Acid Thioester Synthesis: Thiol-Dependent Amino Acid Synthesis from Formose substrates (Formaldehyde and Glycolaldehyde) and Ammonia

Science.gov (United States)

Weber, Arthur L.

1998-01-01

Formaldehyde and glycolaldehyde (substrates of the formose autocatalytic cycle) were shown to react with ammonia yielding alanine and homoserine under mild aqueous conditions in the presence of thiol catalysts. Since similar reactions carried out without ammonia yielded alpha-hydroxy acid thioesters, the thiol-dependent synthesis of alanine and homoserine is presumed to occur via amino acid thioesters-intermediates capable of forming peptides. A pH 5.2 solution of 20 mM formaldehyde, 20 mM glycolaldehyde, 20 mM ammonium chloride, 23 mM 3-mercaptopropionic acid, and 23 mM acetic acid that reacted for 35 days at 40 C yielded (based on initial formaldehyde) 1.8% alanine and 0.08% homoserine. In the absence of thiol catalyst, the synthesis of alanine and homoserine was negligible. Alanine synthesis required both formaldehyde and glycolaldehyde, but homoserine synthesis required only glycolaldehyde. At 25 days the efficiency of alanine synthesis calculated from the ratio of alanine synthesized to formaldehyde reacted was 2.1%, and the yield (based on initial formaldehyde) of triose and tetrose intermediates involved in alanine and homoserine synthesis was 0.3 and 2.1%, respectively. Alanine synthesis was also seen in similar reactions containing only 10 mM each of aldehyde substrates, ammonia, and thiol. The prebiotic significance of these reactions that use the formose reaction to generate sugar intermediates that are converted to reactive amino acid thioesters is discussed.

Preliminary Study on Purification and Identification of Aromatic Acid Amino L-Dopa From Malaysia Freshwater Green Mussel Byssus

International Nuclear Information System (INIS)

Saiful Irwan Zubairi; Wan Rosmaryana Wan Musa; Syed Anuar Faua'ad Syed Mohammad

2014-01-01

L-DOPA (L-3, 4-dihydroxyphenylalanine) is a type of aromatic amino acid which can be detected by using acidic extraction and purification method involving adhesive byssus green mussel protein. The main objective of this study is to identify and purify the aromatic amino acid L-DOPA via the utilization of gel Sephadex G-200 filtration chromatography based on two types of acidic and basic mobile phase solution. The crushing and homogenizing for adhesive byssus green mussel were conducted using a mortar and a pestle with the aid of liquid nitrogen. The samples that had been crushed were then mixed and dissolved in perchloric acid 0.7 %, 1.0 % and 1.5 % (v/ v) (pre-treatment) prior to the extraction process. The extraction was carried out by centrifuging the extracts at 11,000 rpm for about 10 mins and at a temperature of 10 degree Celsius to obtain supernatant S1. The supernatant was mixed with acetone and sulphuric acid and centrifuged for the second time to produce a pellet and then it was dissolved in the respective mobile phase solutions prior to purification process. Purification was later performed using two mobile phase solutions which were acetic acid 5 % (v/ v) and NaOH 1 M. The absorbance (abs) value of each purified protein extract fractions was collected and analysed at 214 nm to 400 nm with the help of UV-spectrophotometer. The highest abs value was selected for identification and verification of amino acid L-DOPA in the purified solution. Verification was carried out by utilizing high performance liquid chromatography (HPLC) and thin layer chromatography (TLC). The results showed that the use of 0.7 % (v/ v) perchloric acid and 5 % (v/ v) acetic acid for pre-treatment process and mobile phase solution of purification process respectively, yielded the highest effluent abs profile at a wavelength of 260 nm. TLC analysis proved the existence of several important amino acids besides L-DOPA which were tyrosine and phenylalanine after 78 hrs of collection of

Prenatal exposure to methylazoxymethanol acetate in the rat alters neurotrophin levels and behavior : considerations for neurodevelopmental diseases

NARCIS (Netherlands)

Fiore, M; Korf, J; Angelucci, F; Talamini, L; Aloe, L

2000-01-01

We did a single injection of methylazoxymethanol acetate (MAM) in pregnant rats on gestational day (GD) 11 or 12 to investigate the long-lasting effects of early entorhinal cortex (EC) and hippocampus maldevelopment on behavior, brain nerve growth factor (NGF) and brain-derived neurotrophic factor

Fixing of metallic acetates on an anion-exchange resin; Fixation d'acetates metalliques dans une resine echangeuse d'anions

Energy Technology Data Exchange (ETDEWEB)

Brigaudeau-Vaissiere, M [Commissariat a l' Energie Atomique, Fontenay-aux-Roses (France). Centre d' Etude Nucleaires

1966-06-01

After giving a brief review of the theoretical principles governing the fixation of anionic complexes of metallic elements on an anion exchange resin, we consider the particular case of uranyl acetate. By plotting the partition curves we have been able to calculate the exchange constants in the resin. By studying the changes in the logarithm of the limiting partition coefficient as a function of the logarithm of the free acetate ion concentration, it has been possible to calculate the dissociation constants for the complexes in solution. The fixation of a large number of metallic acetates has been studied. All the tests have been negative except in the case of mercury. For this reason we have been able to consider the possibility of separating uranium from a certain number of elements. Some of these separations are possible even in the presence of interfering anions such as chlorides which have a greater affinity for the resin than have the acetate ions. In the case of water-ethanol and water-isopropanol mixtures, we have improved the conditions under which copper acetate and mercury acetate may be fixed. This study has enabled us to calculate the dissociation constant for the CuAc{sub 3}{sup -} complex in the mixtures water +40% (by weight) isopropanol and water +50% (by weight) isopropanol. It should also make it possible to use separation conditions which could not hitherto be applied in aqueous media. (author) [French] Apres avoir rappele les principes theoriques de la fixation des complexes anioniques des elements metalliques dans une resine echangeuse d'anions, nous avons etudie tout particulierement le cas de l'acetate d'uranyle. Le trace des courbes de partage nous a permis de calculer les constantes d'echange dans la resine. L'etude des variations du logarithme du coefficient limite de partage avec le logarithme de la concentration des ions acetate libres nous a conduits aux calculs des constantes de dissociation des complexes en solution. La fixation d

Glycerol transesterification with ethyl acetate to synthesize acetins using ethyl acetate as reactant and entrainer

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Amin Shafiei

2017-03-01

Full Text Available Transesterification of glycerol with ethyl acetate was performed over acidic catalysts in the batch and semi-batch systems. Ethyl acetate was used as reactant and entrainer to remove the produced ethanol during the reaction, through azeotrope formation. Since the azeotrope of ethyl acetate and ethanol forms at 70 oC, all the experiments were performed at this temperature. Para-toluene sulfonic acid, sulfuric acid, and Amberlyst 36 were used as catalyst. The effect of process parameters including ethyl acetate to glycerol molar ratio (6-12, reaction time (3-9 h, and the catalyst to glycerol weight (2.5-9.0%, on the conversion and products selectivities were investigated. Under reflux conditions, 100% glycerol conversion was obtained with 45%, 44%, and 11% selectivity to monoacetin, diacetin, and triacetin, respectively. Azeotropic reactive distillation led to 100% conversion of glycerol with selectivities of 3%, 48% and 49% for monoacetin, diacetin, and triacetin. During the azeotropic reactive distillation, it was possible to remove ethanol to shift the equilibrium towards diacetin and triacetin. Therefore, the total selectivity to diacetin and triacetin was increased from 55% to 97% through azeotropic distillation.

Fermentation characteristics of Fusarium oxysporum grown on acetate

DEFF Research Database (Denmark)

Panagiotou, Gianni; Pachidou, Fotini; Petroutsos, Dimitris

2008-01-01

In this study, the growth characteristics of Fusarium oxysporum were evaluated in minimal medium using acetate or different mixtures of acetate and glucose as carbon source. The minimum inhibitory concentration (MIC) of acetic acid that F oxysporum cells could tolerate was 0.8% w/v while glucose ...

Amino-Functionalized Luminescent Metal-Organic Framework Test Paper for Rapid and Selective Sensing of SO2 Gas and Its Derivatives by Luminescence Turn-On Effect.

Science.gov (United States)

Wang, Meng; Guo, Lin; Cao, Dapeng

2018-03-06

Rapid and selective sensing of sulfur dioxide (SO 2 ) gas has attracted more and more attention because SO 2 not only causes environmental pollution but also severely affects the health of human beings. Here we report an amino-functionalized luminescent metal-organic framework (MOF) material (i.e., MOF-5-NH 2 ) and further investigate its sensing property for SO 2 gas and its derivatives as a luminescent probe. The results indicate that the MOF-5-NH 2 probe can selectively and sensitively sense SO 2 derivatives (i.e., SO 3 2- ) in real time by a luminescence turn-on effect with a lower detection limit of 0.168 ppm and a response time of less than 15 s. Importantly, the luminescence turn-on phenomenon can be observed by the naked eye. We also assembled MOF-5-NH 2 into a test paper to achieve the aim of portable detection, and the lower-limit concentration of the test paper for sensing SO 2 in real time was found to be about 0.05 ppm. Moreover, MOF-5-NH 2 also shows good anti-interference ability, strong luminescence stability, and reusability, which means that this material is an excellent sensing candidate. The amino functionalization may also provide a modification strategy to design luminescent sensors for other atmospheric pollutants.

Modification of wheat starch with succinic acid/acetic anhydride and azelaic acid/acetic anhydride mixtures I. Thermophysical and pasting properties.

Science.gov (United States)

Subarić, Drago; Ačkar, Durđica; Babić, Jurislav; Sakač, Nikola; Jozinović, Antun

2014-10-01

The aim of this research was to investigate the influence of modification with succinic acid/acetic anhydride and azelaic acid/acetic anhydride mixtures on thermophysical and pasting properties of wheat starch. Starch was isolated from two wheat varieties and modified with mixtures of succinic acid and acetic anhydride, and azelaic acid and acetic anhydride in 4, 6 and 8 % (w/w). Thermophysical, pasting properties, swelling power, solubility and amylose content of modified starches were determined. The results showed that modifications with mixtures of afore mentioned dicarboxylic acids with acetic anhydride decreased gelatinisation and pasting temperatures. Gelatinisation enthalpy of Golubica starch increased, while of Srpanjka starch decreased by modifications. Retrogradation after 7 and 14 day-storage at 4 °C decreased after modifications of both starches. Maximum, hot and cold paste viscosity of both starches increased, while stability during shearing at high temperatures decreased. % setback of starches modified with azelaic acid/acetic anhydride mixture decreased. Swelling power and solubility of both starches increased by both modifications.

Genetic variation in food choice behaviour of amino acid-deprived Drosophila.

Science.gov (United States)

Toshima, Naoko; Hara, Chieko; Scholz, Claus-Jürgen; Tanimura, Teiichi

2014-10-01

To understand homeostatic regulation in insects, we need to understand the mechanisms by which they respond to external stimuli to maintain the internal milieu. Our previous study showed that Drosophila melanogaster exhibit specific amino acid preferences. Here, we used the D.melanogaster Genetic Reference Panel (DGRP), which is comprised of multiple inbred lines derived from a natural population, to examine how amino acid preference changes depending on the internal nutritional state in different lines. We performed a two-choice preference test and observed genetic variations in the response to amino acid deprivation. For example, a high-responding line showed an enhanced preference for amino acids even after only 1day of deprivation and responded to a fairly low concentration of amino acids. Conversely, a low-responding line showed no increased preference for amino acids after deprivation. We compared the gene expression profiles between selected high- and the low-responding lines and performed SNP analyses. We found several groups of genes putatively involved in altering amino acid preference. These results will contribute to future studies designed to explore how the genetic architecture of an organism evolves to adapt to different nutritional environments. Copyright © 2014 Elsevier Ltd. All rights reserved.

Influence of calcium acetate on rye bread volume

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Katharina FUCKERER

2016-01-01

Full Text Available Abstract The positive accepted savoury taste of rye bread is dependent on acetate concentration in the dough of such breads. In order to study how calcium acetate influences rye bread properties, the pH of rye doughs fortified with calcium acetate and the resulting volume of the breads were measured. Furthermore, CO2 formation of yeast with added calcium acetate and yeast with different pH levels (4, 7, 9 were measured. Thereby, it was determined that the addition of calcium acetate increased the pH of dough from 4.42 to 5.29 and significantly reduced the volume of the breads from 1235.19 mL to 885.52 mL. It could be proven that bread volume was affected by a 30.9% lower CO2 amount production of yeast, although bread volume was not affected by changing pH levels. Due to reduced bread volume, high concentrations of calcium acetate additions are not recommended for improving rye bread taste.

Application of UHPLC for the determination of free amino acids in different cheese varieties.

Science.gov (United States)

Mayer, Helmut K; Fiechter, Gregor

2013-10-01

A rapid ultra-high performance liquid chromatography (UHPLC) protocol for the determination of amino acids as their respective 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) derivatives was successfully applied for assessing free amino acid levels in commercial cheese samples representing typical product groups (ripening protocols) in cheesemaking. Based on the Waters AccQ.Tag™ method as a high performance liquid chromatography (HPLC) amino acid solution designed for hydrolyzate analyses, method adaptation onto UHPLC was performed, and detection of AQC derivatives was changed from former fluorescence (λ(Ex) 250 nm/λ(Em) 395 nm) to UV (254 nm). Compared to the original HPLC method, UHPLC proved to be superior by facilitating excellent separations of 18 amino acids within 12 min only, thus demonstrating significantly shortened runtimes (>35 min for HPLC) while retaining the original separation chemistry and amino acid elution pattern. Free amino acid levels of the analyzed cheese samples showed a high extent of variability depending on the cheese type, with highest total amounts found for original Italian extra-hard cheeses (up to 9,000 mg/100 g) and lowest for surface mold- or bacterial smear-ripened soft cheeses (200-600 mg/100 g). Despite the intrinsic variability in both total and specific concentrations, the established UHPLC method enabled reliable and interference-free amino acid profiling throughout all cheese types, thus demonstrating a valuable tool to generate high quality data for the characterization of cheese ripening.

Study of alkaline-earth element complexes in anhydrous acetic acid

International Nuclear Information System (INIS)

Petit, N.

1968-10-01

We have studied the complexes of alkaline-earth elements in anhydrous acetic acid. Using glass-electrode potentiometry we have studied the titration of alkaline earth acetates with perchloric acid which is the strongest acid in anhydrous acetic acid. These titrations have shown that the basic strength of these acetates increases as follows: Mg 4 ); the mixed acetate-acid sulfate complex of barium: Ba (OAc)(HSO 4 ); the mixed acetate-chloride of barium: Ba (OAc)(Cl). (author) [fr

Techno-economic Analysis for the Thermochemical Conversion of Lignocellulosic Biomass to Ethanol via Acetic Acid Synthesis

Energy Technology Data Exchange (ETDEWEB)

Zhu, Yunhua; Jones, Susanne B.

2009-04-01

Biomass is a renewable energy resource that can be converted into liquid fuel suitable for transportation applications. As a widely available biomass form, lignocellulosic biomass can have a major impact on domestic transportation fuel supplies and thus help meet the Energy Independence and Security Act renewable energy goals (U.S. Congress 2007). This study performs a techno-economic analysis of the thermo chemical conversion of biomass to ethanol, through methanol and acetic acid, followed by hydrogenation of acetic acid to ethanol. The conversion of syngas to methanol and methanol to acetic acid are well-proven technologies with high conversions and yields. This study was undertaken to determine if this highly selective route to ethanol could provide an already established economically attractive route to ethanol. The feedstock was assumed to be wood chips at 2000 metric ton/day (dry basis). Two types of gasification technologies were evaluated: an indirectly-heated gasifier and a directly-heated oxygen-blown gasifier. Process models were developed and a cost analysis was performed. The carbon monoxide used for acetic acid synthesis from methanol and the hydrogen used for hydrogenation were assumed to be purchased and not derived from the gasifier. Analysis results show that ethanol selling prices are estimated to be $2.79/gallon and $2.81/gallon for the indirectly-heated gasifier and the directly-heated gasifier systems, respectively (1stQ 2008$, 10% ROI). These costs are above the ethanol market price for during the same time period ($1.50 - $2.50/gal). The co-production of acetic acid greatly improves the process economics as shown in the figure below. Here, 20% of the acetic acid is diverted from ethanol production and assumed to be sold as a co-product at the prevailing market prices ($0.40 - $0.60/lb acetic acid), resulting in competitive ethanol production costs.

Oxidative diversification of amino acids and peptides by small-molecule iron catalysis.

Science.gov (United States)

Osberger, Thomas J; Rogness, Donald C; Kohrt, Jeffrey T; Stepan, Antonia F; White, M Christina

2016-09-08

Secondary metabolites synthesized by non-ribosomal peptide synthetases display diverse and complex topologies and possess a range of biological activities. Much of this diversity derives from a synthetic strategy that entails pre- and post-assembly oxidation of both the chiral amino acid building blocks and the assembled peptide scaffolds. The vancomycin biosynthetic pathway is an excellent example of the range of oxidative transformations that can be performed by the iron-containing enzymes involved in its biosynthesis. However, because of the challenges associated with using such oxidative enzymes to carry out chemical transformations in vitro, chemical syntheses guided by these principles have not been fully realized in the laboratory. Here we report that two small-molecule iron catalysts are capable of facilitating the targeted C-H oxidative modification of amino acids and peptides with preservation of α-centre chirality. Oxidation of proline to 5-hydroxyproline furnishes a versatile intermediate that can be transformed to rigid arylated derivatives or flexible linear carboxylic acids, alcohols, olefins and amines in both monomer and peptide settings. The value of this C-H oxidation strategy is demonstrated in its capacity for generating diversity: four 'chiral pool' amino acids are transformed to twenty-one chiral unnatural amino acids representing seven distinct functional group arrays; late-stage C-H functionalizations of a single proline-containing tripeptide furnish eight tripeptides, each having different unnatural amino acids. Additionally, a macrocyclic peptide containing a proline turn element is transformed via late-stage C-H oxidation to one containing a linear unnatural amino acid.

Flux Analysis of Free Amino Sugars and Amino Acids in Soils by Isotope Tracing with a Novel Liquid Chromatography/High Resolution Mass Spectrometry Platform.

Science.gov (United States)

Hu, Yuntao; Zheng, Qing; Wanek, Wolfgang

2017-09-05

Soil fluxomics analysis can provide pivotal information for understanding soil biochemical pathways and their regulation, but direct measurement methods are rare. Here, we describe an approach to measure soil extracellular metabolite (amino sugar and amino acid) concentrations and fluxes based on a 15 N isotope pool dilution technique via liquid chromatography and high-resolution mass spectrometry. We produced commercially unavailable 15 N and 13 C labeled amino sugars and amino acids by hydrolyzing peptidoglycan isolated from isotopically labeled bacterial biomass and used them as tracers ( 15 N) and internal standards ( 13 C). High-resolution (Orbitrap Exactive) MS with a resolution of 50 000 allowed us to separate different stable isotope labeled analogues across a large range of metabolites. The utilization of 13 C internal standards greatly improved the accuracy and reliability of absolute quantification. We successfully applied this method to two types of soils and quantified the extracellular gross fluxes of 2 amino sugars, 18 amino acids, and 4 amino acid enantiomers. Compared to the influx and efflux rates of most amino acids, similar ones were found for glucosamine, indicating that this amino sugar is released through peptidoglycan and chitin decomposition and serves as an important nitrogen source for soil microorganisms. d-Alanine and d-glutamic acid derived from peptidoglycan decomposition exhibited similar turnover rates as their l-enantiomers. This novel approach offers new strategies to advance our understanding of the production and transformation pathways of soil organic N metabolites, including the unknown contributions of peptidoglycan and chitin decomposition to soil organic N cycling.

Flux Analysis of Free Amino Sugars and Amino Acids in Soils by Isotope Tracing with a Novel Liquid Chromatography/High Resolution Mass Spectrometry Platform

Science.gov (United States)

2017-01-01

Soil fluxomics analysis can provide pivotal information for understanding soil biochemical pathways and their regulation, but direct measurement methods are rare. Here, we describe an approach to measure soil extracellular metabolite (amino sugar and amino acid) concentrations and fluxes based on a 15N isotope pool dilution technique via liquid chromatography and high-resolution mass spectrometry. We produced commercially unavailable 15N and 13C labeled amino sugars and amino acids by hydrolyzing peptidoglycan isolated from isotopically labeled bacterial biomass and used them as tracers (15N) and internal standards (13C). High-resolution (Orbitrap Exactive) MS with a resolution of 50 000 allowed us to separate different stable isotope labeled analogues across a large range of metabolites. The utilization of 13C internal standards greatly improved the accuracy and reliability of absolute quantification. We successfully applied this method to two types of soils and quantified the extracellular gross fluxes of 2 amino sugars, 18 amino acids, and 4 amino acid enantiomers. Compared to the influx and efflux rates of most amino acids, similar ones were found for glucosamine, indicating that this amino sugar is released through peptidoglycan and chitin decomposition and serves as an important nitrogen source for soil microorganisms. d-Alanine and d-glutamic acid derived from peptidoglycan decomposition exhibited similar turnover rates as their l-enantiomers. This novel approach offers new strategies to advance our understanding of the production and transformation pathways of soil organic N metabolites, including the unknown contributions of peptidoglycan and chitin decomposition to soil organic N cycling. PMID:28776982

Ru decorated carbon nanotubes - a promising catalyst for reforming bio-based acetic acid in the aqueous phase

NARCIS (Netherlands)

de Vlieger, Dennis; Lefferts, Leonardus; Seshan, Kulathuiyer

2014-01-01

Catalytic reforming of biomass derived waste streams in the aqueous phase is a promising process for the production of sustainable hydrogen. Acetic acid will be a major component (up to 20 wt%) in many anticipated gasification feed streams (e.g. the aqueous fraction of pyrolysis oil). Conventional

21 CFR 177.1350 - Ethylene-vinyl acetate copolymers.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Ethylene-vinyl acetate copolymers. 177.1350 Section... Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1350 Ethylene-vinyl acetate copolymers. Ethylene-vinyl acetate copolymers may be safely used as articles or components of articles...

Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases

Directory of Open Access Journals (Sweden)

Eva Vavříková

2015-05-01

Full Text Available A panel of lipases was screened for the selective acetylation and alcoholysis of silychristin and silychristin peracetate, respectively. Acetylation at primary alcoholic group (C-22 of silychristin was accomplished by lipase PS (Pseudomonas cepacia immobilized on diatomite using vinyl acetate as an acetyl donor, whereas selective deacetylation of 22-O-acetyl silychristin was accomplished by Novozym 435 in methyl tert-butyl ether/ n-butanol. Both of these reactions occurred without diastereomeric discrimination of silychristin A and B. Both of these enzymes were found to be capable to regioselective deacetylation of hexaacetyl silychristin to afford penta-, tetra- and tri-acetyl derivatives, which could be obtained as pure synthons for further selective modifications of the parent molecule.

Desmopressin Acetate in Intracranial Haemorrhage

Directory of Open Access Journals (Sweden)

Thomas Kapapa

2014-01-01

Full Text Available Introduction. The secondary increase in the size of intracranial haematomas as a result of spontaneous haemorrhage or trauma is of particular relevance in the event of prior intake of platelet aggregation inhibitors. We describe the effect of desmopressin acetate as a means of temporarily stabilising the platelet function. Patients and Methods. The platelet function was analysed in 10 patients who had received single (N=4 or multiple (N=6 doses of acetylsalicylic acid and 3 patients (control group who had not taken acetylsalicylic acid. All subjects had suffered intracranial haemorrhage. Analysis was performed before, half an hour and three hours after administration of desmopressin acetate. Statistical analysis was performed by applying a level of significance of P≤0.05. Results. (1 Platelet function returned to normal 30 minutes after administration of desmopressin acetate. (2 The platelet function worsened again after three hours. (3 There were no complications related to electrolytes or fluid balance. Conclusion. Desmopressin acetate can stabilise the platelet function in neurosurgical patients who have received acetylsalicylic acid prior to surgery without causing transfusion-related side effects or a loss of time. The effect is, however, limited and influenced by the frequency of drug intake. Further controls are needed in neurosurgical patients.

Correlation of vapor - liquid equilibrium data for acetic acid - isopropanol - water - isopropyl acetate mixtures

Directory of Open Access Journals (Sweden)

B. A. Mandagarán

2006-03-01

Full Text Available A correlation procedure for the prediction of vapor - liquid equilibrium of acetic acid - isopropanol - water - isopropyl acetate mixtures has been developed. It is based on the NRTL model for predicting liquid activity coefficients, and on the Hayden-O'Connell second virial coefficients for predicting the vapor phase of systems containing association components. When compared with experimental data the correlation shows a good agreement for binary and ternary data. The correlation also shows good prediction for reactive quaternary data.

Annotating Enzymes of Uncertain Function: The Deacylation of d-Amino Acids by Members of the Amidohydrolase Superfamily

Energy Technology Data Exchange (ETDEWEB)

Cummings, J.; Fedorov, A; Xu, C; Brown, S; Fedorov, E; Babbitt, P; Almo, S; Raushel, F

2009-01-01

The catalytic activities of three members of the amidohydrolase superfamily were discovered using amino acid substrate libraries. Bb3285 from Bordetella bronchiseptica, Gox1177 from Gluconobacter oxidans, and Sco4986 from Streptomyces coelicolor are currently annotated as d-aminoacylases or N-acetyl-d-glutamate deacetylases. These three enzymes are 22-34% identical to one another in amino acid sequence. Substrate libraries containing nearly all combinations of N-formyl-d-Xaa, N-acetyl-d-Xaa, N-succinyl-d-Xaa, and l-Xaa-d-Xaa were used to establish the substrate profiles for these enzymes. It was demonstrated that Bb3285 is restricted to the hydrolysis of N-acyl-substituted derivatives of d-glutamate. The best substrates for this enzyme are N-formyl-d-glutamate (k{sub cat}/K{sub m} = 5.8 x 10{sup 6} M{sup -1} s{sup -1}), N-acetyl-d-glutamate (k{sub cat}/K{sub m} = 5.2 x 10{sup 6} M{sup -1} s{sup -1}), and l-methionine-d-glutamate (k{sub cat}/K{sub m} = 3.4 x 10{sup 5} M{sup -1} s{sup -1}). Gox1177 and Sco4986 preferentially hydrolyze N-acyl-substituted derivatives of hydrophobic d-amino acids. The best substrates for Gox1177 are N-acetyl-d-leucine (k{sub cat}/K{sub m} = 3.2 x 104 M{sup -1} s-1), N-acetyl-d-tryptophan (kcat/Km = 4.1 x 104 M-1 s-1), and l-tyrosine-d-leucine (kcat/Km = 1.5 x 104 M-1 s-1). A fourth protein, Bb2785 from B. bronchiseptica, did not have d-aminoacylase activity. The best substrates for Sco4986 are N-acetyl-d-phenylalanine and N-acetyl-d-tryptophan. The three-dimensional structures of Bb3285 in the presence of the product acetate or a potent mimic of the tetrahedral intermediate were determined by X-ray diffraction methods. The side chain of the d-glutamate moiety of the inhibitor is ion-paired to Arg-295, while the {alpha}-carboxylate is ion-paired with Lys-250 and Arg-376. These results have revealed the chemical and structural determinants for substrate specificity in this protein. Bioinformatic analyses of an additional {approx}250

Degradation of fructans and production of propionic acid by Bacteroides thetaiotaomicron are enhanced by shortage of amino acids

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Signe eAdamberg

2014-12-01

Full Text Available Bacteroides thetaiotaomicron is commonly found in the human colon and stabilizes its ecosystem by the catabolism of various polysaccharides. A model of cross-talk between the metabolism of amino acids and fructans in B. thetaiotaomicron was proposed. The growth of B. thetaiotaomicron DSM 2079 in two defined media containing mineral salts and vitamins, and supplemented with either 20 or 2 amino acids, was studied in an isothermal microcalorimeter. The polyfructans inulin (from chicory and levan (synthesized using levansucrase from Pseudomonas syringae, two fructooligosaccharide preparations with different composition, sucrose and fructose were tested as substrates. The calorimetric power-time curves were substrate specific and typically multiauxic. A surplus of amino acids reduced the consumption of longer oligosaccharides (DP > 3. Bacterial growth was not detected either in the carbohydrate free medium containing amino acids or in the medium with inulin as a sole carbohydrate. In amino acid-restricted medium, fermentation leading to acetic acid formation was dominant at the beginning of growth (up to 24 h, followed by increased lactic acid production, and mainly propionic and succinic acids were produced at the end of fermentation. In the medium supplemented with 20 amino acids, the highest production of D-lactate (82 ± 33 mmol/gDW occurred in parallel with extensive consumption (up to 17 mmol/gDW of amino acids, especially Ser, Thr and Asp. The production of Ala and Glu was observed at growth on all substrates, and the production was enhanced under amino acid deficiency. The study revealed the influence of amino acids on fructan metabolism in B. thetaiotaomicron and showed that defined growth media are invaluable in elucidating quantitative metabolic profiles of the bacteria. Levan was shown to act as an easily degradable substrate for B. thetaiotaomicron. The effect of levan on balancing or modifying colon microbiota will be studied in

Facile preparation of amine and amino acid adducts of [60]fullerene using chlorofullerene C60Cl6 as a precursor.

Science.gov (United States)

Kornev, Alexey B; Khakina, Ekaterina A; Troyanov, Sergey I; Kushch, Alla A; Peregudov, Alexander; Vasilchenko, Alexey; Deryabin, Dmitry G; Martynenko, Vyacheslav M; Troshin, Pavel A

2012-06-04

We report a general synthetic approach to the preparation of highly functionalized amine and amino acid derivatives of [60]fullerene starting from readily available chlorofullerene C(60)Cl(6). The synthesized water-soluble amino acid derivative of C(60) demonstrated pronounced antiviral activity, while the cationic amine-based compound showed strong antibacterial action in vitro.

N-Benzylhydroxylamine addition to beta-aryl enoates. Enantioselective synthesis of beta-aryl-beta-amino acid precursors

Science.gov (United States)

Sibi; Liu

2000-10-19

Chiral Lewis acid catalyzed N-benzylhydroxylamine addition to pyrrolidinone-derived enoates afforded beta-aryl-beta-amino acid derivatives in high enantiomeric purity with moderate to very good chemical efficiency.

Acid-catalyzed rearrangements of flavans to novelbenzofuran derivatives

Science.gov (United States)

Richard W. Hemingway; Weiling Peng; Anthony H. Conner; Petrus J. Steynberg; Jan P. Steynberg

1998-01-01

The objective of this work was to define reactions that occur when proanthocyanidins and their derivatives are reacted in the presence of acid catalysts. Pure compounds (either as the free phenols, the methyl ether, or the methyl ether-acetate derivatives) were isolated by a variety of chromatographic methods. Proof of their structure was based mainly on 2D-NMR, as...

Aerobic oxidation of aqueous ethanol using heterogeneous gold catalysts: Efficient routes to acetic acid and ethyl acetate

DEFF Research Database (Denmark)

Jørgensen, Betina; Christiansen, Sofie Egholm; Thomsen, M.L.D.

2007-01-01

The aerobic oxidation of aqueous ethanol to produce acetic acid and ethyl acetate was studied using heterogeneous gold catalysts. Comparing the performance of Au/MgAl2O4 and Au/TiO2 showed that these two catalysts exhibited similar performance in the reaction. By proper selection of the reaction...

An OmpA family protein, a target of the GinI/GinR quorum-sensing system in Gluconacetobacter intermedius, controls acetic acid fermentation.

Science.gov (United States)

Iida, Aya; Ohnishi, Yasuo; Horinouchi, Sueharu

2008-07-01

Via N-acylhomoserine lactones, the GinI/GinR quorum-sensing system in Gluconacetobacter intermedius NCI1051, a gram-negative acetic acid bacterium, represses acetic acid and gluconic acid fermentation. Two-dimensional polyacrylamide gel electrophoretic analysis of protein profiles of strain NCI1051 and ginI and ginR mutants identified a protein that was produced in response to the GinI/GinR regulatory system. Cloning and nucleotide sequencing of the gene encoding this protein revealed that it encoded an OmpA family protein, named GmpA. gmpA was a member of the gene cluster containing three adjacent homologous genes, gmpA to gmpC, the organization of which appeared to be unique to vinegar producers, including "Gluconacetobacter polyoxogenes." In addition, GmpA was unique among the OmpA family proteins in that its N-terminal membrane domain forming eight antiparallel transmembrane beta-strands contained an extra sequence in one of the surface-exposed loops. Transcriptional analysis showed that only gmpA of the three adjacent gmp genes was activated by the GinI/GinR quorum-sensing system. However, gmpA was not controlled directly by GinR but was controlled by an 89-amino-acid protein, GinA, a target of this quorum-sensing system. A gmpA mutant grew more rapidly in the presence of 2% (vol/vol) ethanol and accumulated acetic acid and gluconic acid in greater final yields than strain NCI1051. Thus, GmpA plays a role in repressing oxidative fermentation, including acetic acid fermentation, which is unique to acetic acid bacteria and allows ATP synthesis via ethanol oxidation. Consistent with the involvement of gmpA in oxidative fermentation, its transcription was also enhanced by ethanol and acetic acid.

Decreased panicle-derived indole-3-acetic acid reduces gibberellin A1 level in the uppermost internode, causing panicle enclosure in male sterile rice Zhenshan 97A.

Science.gov (United States)

Yin, Changxi; Gan, Lijun; Ng, Denny; Zhou, Xie; Xia, Kai

2007-01-01

Cytoplasmic male sterile (CMS) rice Zhenshan 97A (ZS97A) has been widely used in hybrid rice production in China. However, ZS97A suffers from serious panicle enclosure, which blocks normal pollination and greatly reduces seed production of hybrid rice. Little is known about the cause of panicle closure in ZS97A. In this study, it was found that the occurrence of cytoplasmic male sterility caused a deficiency of indole-3-acetic acid (IAA) in ZS97A panicles, and less IAA was provided to the uppermost internode (UI). Further, it was found that the decreased panicle-derived IAA caused a gibberellin A(1) (GA(1)) deficiency in the UI by the down-regulation of OsGA3ox2 transcript level. Reduced GA(1) level in the UI led to decreases of both cell number and cell elongation, resulting in a shortened UI. The shortened UI was unable to push the panicle out of the flag leaf sheath that remained normal, which resulted in panicle enclosure in ZS97A. These findings suggest that decreased panicle-derived IAA reduces the GA(1) level in the UI, causing panicle enclosure in CMS rice ZS97A.

Synthesis and biological evaluation of novel gramicidin s analogues

NARCIS (Netherlands)

Tuin, A.W.; Palachanis, D.K.; Buizert, A.; Grotenbreg, G.M.; Spalburg, E.; Neeling, A.J. de; Mars-Groenendijk, R.H.; Noort, D.; Marel, G.A. van der; Overkleeft, H.S.; Overhand, M.

2009-01-01

The synthesis of three new analogues of the cyclic cationic antimicrobial peptide Gramicidin S is described. These derivatives contain a modified turn region in which the DPhe-Pro motif has been replaced by a constrained furanoid sugar amino acid or a flexible linear aminoethoxy acetic acid moiety.

Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α-Amino Acid or Amino Alcohol without Chiral Reagent.

Science.gov (United States)

Mai, Thi Thoa; Viswambharan, Baby; Gori, Didier; Guillot, Régis; Naubron, Jean-Valère; Kouklovsky, Cyrille; Alezra, Valérie

2017-04-27

One of the fundamental and intriguing aspects of life is the homochirality of the essential molecules. In this field, the absolute asymmetric synthesis of α-amino acids is a major challenge. Herein, we report access, by chemical means, to tertiary α-amino acid derivatives in up to 96 % ee without using any chiral reagent. In our strategy, the dynamic axial chirality of tertiary aromatic amides is frozen in a crystal and is responsible for the stereoselectivity of the subsequent steps. Furthermore, we could control the configuration of the final product by manually sorting and selecting the initial crystals. Based on vibrational circular dichroism studies, we could rationalize the observed stereoselectivity. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Brain glutamine synthesis requires neuronal-born aspartate as amino donor for glial glutamate formation.

Science.gov (United States)

Pardo, Beatriz; Rodrigues, Tiago B; Contreras, Laura; Garzón, Miguel; Llorente-Folch, Irene; Kobayashi, Keiko; Saheki, Takeyori; Cerdan, Sebastian; Satrústegui, Jorgina

2011-01-01

The glutamate-glutamine cycle faces a drain of glutamate by oxidation, which is balanced by the anaplerotic synthesis of glutamate and glutamine in astrocytes. De novo synthesis of glutamate by astrocytes requires an amino group whose origin is unknown. The deficiency in Aralar/AGC1, the main mitochondrial carrier for aspartate-glutamate expressed in brain, results in a drastic fall in brain glutamine production but a modest decrease in brain glutamate levels, which is not due to decreases in neuronal or synaptosomal glutamate content. In vivo (13)C nuclear magnetic resonance labeling with (13)C(2)acetate or (1-(13)C) glucose showed that the drop in brain glutamine is due to a failure in glial glutamate synthesis. Aralar deficiency induces a decrease in aspartate content, an increase in lactate production, and lactate-to-pyruvate ratio in cultured neurons but not in cultured astrocytes, indicating that Aralar is only functional in neurons. We find that aspartate, but not other amino acids, increases glutamate synthesis in both control and aralar-deficient astrocytes, mainly by serving as amino donor. These findings suggest the existence of a neuron-to-astrocyte aspartate transcellular pathway required for astrocyte glutamate synthesis and subsequent glutamine formation. This pathway may provide a mechanism to transfer neuronal-born redox equivalents to mitochondria in astrocytes.

Enteroendocrine-derived glucagon-like peptide-2 controls intestinal amino acid transport.

Science.gov (United States)

Lee, Jennifer; Koehler, Jacqueline; Yusta, Bernardo; Bahrami, Jasmine; Matthews, Dianne; Rafii, Mahroukh; Pencharz, Paul B; Drucker, Daniel J

2017-03-01

Glucagon-like peptide-2 (GLP-2) is co-secreted with GLP-1 from gut endocrine cells, and both peptides act as growth factors to expand the surface area of the mucosal epithelium. Notably, GLP-2 also enhances glucose and lipid transport in enterocytes; however, its actions on control of amino acid (AA) transport remain unclear. Here we examined the mechanisms linking gain and loss of GLP-2 receptor (GLP-2R) signaling to control of intestinal amino acid absorption in mice. Absorption, transport, and clearance of essential AAs, specifically lysine, were measured in vivo by Liquid Chromatography triple quadrupole Mass Spectrometry (LC-MS/MS) and ex vivo with Ussing chambers using intestinal preparations from Glp2 r +/+ and Glp2r - / - mice. Immunoblotting determined jejunal levels of protein components of signaling pathways (PI3K-AKT, and mTORC1-pS6-p4E-BP1) following administration of GLP-2, protein gavage, and rapamycin to fasted Glp2 r +/+ and Glp2r - / - mice. Expression of AA transporters from full thickness jejunum and 4F2hc from brush border membrane vesicles (BBMVs) was measured by real-time PCR and immunoblotting, respectively. Acute administration of GLP-2 increased basal AA absorption in vivo and augmented basal lysine transport ex vivo . GLP-2-stimulated lysine transport was attenuated by co-incubation with wortmannin, rapamycin, or tetrodotoxin ex vivo . Phosphorylation of mTORC1 effector proteins S6 and 4E-BP1 was significantly increased in wild-type mice in response to GLP-2 alone, or when co-administered with protein gavage, and abolished following oral gavage of rapamycin. In contrast, activation of GLP-1R signaling did not enhance S6 phosphorylation. Disruption of GLP-2 action in Glp2r -/- mice reduced lysine transport ex vivo and attenuated the phosphorylation of S6 and 4E-BP1 in response to oral protein. Moreover, the expression of cationic AA transporter slc7a9 in response to refeeding, and the abundance of 4F2hc in BBMVs following protein

Synthesis of 14C-labeled 3-{[1-ethoxycarbonyl-3-phenyl-(1S)-propyl]amino}-2,3,4,5-tetrahydro-2-oxo -1H-1-(3S)-benzazepine-1-acetic acid hydrochloride ([14C]CGS 14824A)

International Nuclear Information System (INIS)

Chaudhuri, N.K.; Patera, R.; Markus, B.; Mingsang Sung

1987-01-01

The title compound, CGS 14824A, was synthesized with a 14 C-label in the azepine ring in 14 steps starting with 1-bromo-3-phenylpropane (1) and K 14 CN in an overall yield of 1.31%. The reaction of 1 with K 14 CN yielded the nitrile 2 which upon hydrolysis followed by ring closure gave α-tetralone-1- 14 C (4). Bromination of 4 followed by oxime formation gave the bromo oxime 5, which upon Beckmann rearrangement by acid treatment yielded the ring expansion product 6. The bromine atom of 6 was then replaced by an azido group, and an acetic ester side chain was introduced at the nitrogen atom. Catalytic reduction of the azido compound 8 gave a mixture of epimeric amino esters which was resolved by salt formation with L-tartaric acid. The negatively rotating isomer was then reacted with 4-phenyl-2-oxo-butanoate in presence of sodium cyanoborohydride to give a mixture of diastereoisomers which were separated as their benzyl esters by chromatography. The major isomer was then converted to labeled CGS 14824A. (author)

Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids.

Science.gov (United States)

Kiss, Loránd; Nonn, Melinda; Sillanpää, Reijo; Haukka, Matti; Fustero, Santos; Fülöp, Ferenc

2016-12-06

This work describes a substrate-directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH 2 F or CHF 2 moieties in their structure have been synthesized from diexo- or diendo-norbornene β-amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon-carbon double bond of the norbornene β-amino acids, followed by transformation of the resulted "all cis" and "trans" diformyl intermediates by fluorination with "chemodifferentiation". © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Vinyl acetate polymerization by ionizing radiation

International Nuclear Information System (INIS)

Mesquita, Andrea Cercan

2002-01-01

The aim of this work is the synthesis and characterization of the poly(vinyl acetate) using the ionizing radiation. Six polymerizations of vinyl acetate were carried out using three techniques of polymerization: in bulk, emulsion and solution. In the technique of solution polymerization were used two solvents, the alcohol ethyl and the methylethylketone, in two proportions 1:0.5 and 1:1 related to the monomer. The solutions were irradiated with gamma rays from a 60 Co source, with dose rate between 5.25 kGy/h and 6.26 kGy/h. The polymers obtained were characterized by Fourier Transform Infrared Spectroscopy (FTIR). The glass transition temperature (Tg) was investigated by Differential Scanning Calorimeter (DSC). The molecular weight was analyzed by the technique of Gel Permeation Chromatography (GPC). Tests of density, hardness and Vicat softening temperature were carried out. The infrared spectroscopy and others results confirmed that the polymers obtained by polymerization of vinyl acetate in bulk, emulsion and solution, using ionizing radiation, really correspond at poly(vinyl acetate). (author)

Engineered Humicola insolens cutinase for efficient cellulose acetate deacetylation.

Science.gov (United States)

Shirke, Abhijit N; Butterfoss, Glenn L; Saikia, Rakhi; Basu, Aditya; de Maria, Leonardo; Svendsen, Allan; Gross, Richard A

2017-08-01

Cutinases comprise a family of esterases with broad hydrolytic activity for chain and pendant ester groups. This work aimed to identify and improve an efficient cutinase for cellulose acetate (CA) deacetylation. The development of a mild method for CA fiber surface deacetylation will result in improved surface hydrophilicity and reactivity while, when combined with cellulases, a route to the full recycling of CA to acetate and glucose. In this study, the comparative CA deacetylation activity of four homologous wild-type (wt) fungal cutinases from Aspergillus oryzae (AoC), Thiellavia terrestris (TtC), Fusarium solani (FsC), and Humicola insolens (HiC) was determined by analysis of CA deacetylation kinetics. wt-HiC had the highest catalytic efficiency (≈32 [cm 2 L -1 ] -1 h -1 ). Comparison of wt-cutinase catalytic constants revealed that differences in catalytic efficiency are primarily due to corresponding variations in corresponding substrate binding constants. Docking studies with model tetrameric substrates also revealed structural origins for differential substrate binding amongst these cutinases. Comparative docking studies of HiC point mutations led to the identification of two important rationales for engineering cutinases for CA deacetylation: (i) create a tight but not too closed binding groove, (ii) allow for hydrogen bonding in the extended region around the active site. Rationally designed HiC with amino acid substitutions I36S, predicted to hydrogen bond to CA, combined with F70A, predicted to remove steric constraints, showed a two-fold improvement in catalytic efficiency. Continued cutinase optimization guided by a detailed understanding of structure-activity relationships, as demonstrated here, will be an important tool to developing practical cutinases for commercial green chemistry technologies. Copyright © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Determination of 13C isotopic enrichment of valine and threonine by GC-C-IRMS after formation of the N(O,S)-ethoxycarbonyl ethyl ester derivatives of the amino acids.

Science.gov (United States)

Godin, Jean-Philippe; Faure, Magali; Breuille, Denis; Hopfgartner, Gérard; Fay, Laurent-Bernard

2007-06-01

We describe a new method of assessing, in a single run, (13)C isotopic enrichment of both Val and Thr by gas chromatography-combustion-isotope-ratio mass spectrometry (GC-C-IRMS). This method characterised by a rapid one-step derivatisation procedure performed at room temperature to form the N(O,S)-ethoxycarbonyl ethyl ester derivatives, and a polar column for GC. The suitability of this method for Val and Thr in in-vivo samples (mucosal hydrolysate) was demonstrated by studying protein metabolism with two tracers ((13)C-valine or (13)C-threonine). The intra-day and inter-day repeatability were both assessed either with standards or with in-vivo samples at natural abundance and at low (13)C isotopic enrichment. For inter-day repeatability CVs were between 0.8 and 1.5% at natural abundance and lower than 5.5% at 0.112 and 0.190 atom% enrichment for Val and Thr, respectively. Overall isotopic precision was studied for eleven standard amino acid derivatives (those of Val, Ala, Leu, Iso, Gly, Pro, Asp, Thr, Ser, Met, and Phe) and was assessed at 0.32 per thousand. The (13)C isotopic measurement was then extended to the other amino acids (Ala, Val, Leu, Iso, Gly, Pro, Thr, and Phe) at natural abundance for in-vivo samples. The isotopic precision was better than 0.002 atom% per amino acid (for n = 4 rats). This analytical method was finally applied to an animal study to measure Thr utilization in protein synthesis.

Biotechnological applications of acetic acid bacteria.

Science.gov (United States)

Raspor, Peter; Goranovic, Dusan

2008-01-01

The acetic acid bacteria (AAB) have important roles in food and beverage production, as well as in the bioproduction of industrial chemicals. In recent years, there have been major advances in understanding their taxonomy, molecular biology, and physiology, and in methods for their isolation and identification. AAB are obligate aerobes that oxidize sugars, sugar alcohols, and ethanol with the production of acetic acid as the major end product. This special type of metabolism differentiates them from all other bacteria. Recently, the AAB taxonomy has been strongly rearranged as new techniques using 16S rRNA sequence analysis have been introduced. Currently, the AAB are classified in ten genera in the family Acetobacteriaceae. AAB can not only play a positive role in the production of selected foods and beverages, but they can also spoil other foods and beverages. AAB occur in sugar- and alcohol-enriched environments. The difficulty of cultivation of AAB on semisolid media in the past resulted in poor knowledge of the species present in industrial processes. The first step of acetic acid production is the conversion of ethanol from a carbohydrate carried out by yeasts, and the second step is the oxidation of ethanol to acetic acid carried out by AAB. Vinegar is traditionally the product of acetous fermentation of natural alcoholic substrates. Depending on the substrate, vinegars can be classified as fruit, starch, or spirit substrate vinegars. Although a variety of bacteria can produce acetic acid, mostly members of Acetobacter, Gluconacetobacter, and Gluconobacter are used commercially. Industrial vinegar manufacturing processes fall into three main categories: slow processes, quick processes, and submerged processes. AAB also play an important role in cocoa production, which represents a significant means of income for some countries. Microbial cellulose, produced by AAB, possesses some excellent physical properties and has potential for many applications. Other

Effect of fermentation and subsequent pasteurization processes on amino acids composition of orange juice.

Science.gov (United States)

Cerrillo, I; Fernández-Pachón, M S; Collado-González, J; Escudero-López, B; Berná, G; Herrero-Martín, G; Martín, F; Ferreres, F; Gil-Izquierdo, A

2015-06-01

The fermentation of fruit produces significant changes in their nutritional composition. An orange beverage has been obtained from the controlled alcoholic fermentation and thermal pasteurization of orange juice. A study was performed to determine the influence of both processes on its amino acid profile. UHPLC-QqQ-MS/MS was used for the first time for analysis of orange juice samples. Out of 29 amino acids and derivatives identified, eight (ethanolamine, ornithine, phosphoethanolamine, α-amino-n-butyric acid, hydroxyproline, methylhistidine, citrulline, and cystathionine) have not previously been detected in orange juice. The amino acid profile of the orange juice was not modified by its processing, but total amino acid content of the juice (8194 mg/L) was significantly increased at 9 days of fermentation (13,324 mg/L). Although the pasteurization process produced partial amino acid degradation, the total amino acid content was higher in the final product (9265 mg/L) than in the original juice, enhancing its nutritional value.

Recovery of Organic and Amino Acids from Sludge and Fish Waste in Sub Critical Water Conditions

Directory of Open Access Journals (Sweden)

Muhammad Faisal

2011-12-01

Full Text Available The possibility of organic and amino acid production from the treatment of sludge and fish waste using water at sub critical conditions was investigated. The results indicated that at sub-critical conditions, where the ion product of water went through a maximum, the formation of organic acids was favorable. The presence of oxidant favored formation of acetic and formic acid. Other organic acids of significant amount were propionic, succinic and lactic acids. Depending on the type of wastes, formation of other organic acids was also possible. Knowing the organic acids obtained by hydrolysis and oxidation in sub-critical water of various wastes are useful in designing of applicable waste treatment process, complete degradation of organic wastes into volatile carbon and water, and also on the viewpoint of resource recovery. The production of lactic acid was discussed as well. The results indicated that temperature of 573 K, with the absence of oxidant, yield of lactic acid from fish waste was higher than sewage sludge. The maximum yield of total amino acids (137 mg/g-dry fish from waste fish entrails was obtained at subcritical condition (T = 523 K, P = 4 MPa at reaction time of 60 min by using the batch reactor. The amino acids obtained in this study were mainly alanine and glycine. Keywords:  organic acids, amino acids, sub-critical water, hydrothermal, resources recovery

Hydroxyurea derivatives of irofulven with improved antitumor efficacy.

Science.gov (United States)

Staake, Michael D; Kashinatham, Alisala; McMorris, Trevor C; Estes, Leita A; Kelner, Michael J

2016-04-01

Irofulven is a semi-synthetic derivative of Illudin S, a toxic sesquiterpene isolated from the mushroom Omphalotus illudens. Irofulven has displayed significant antitumor activity in various clinical trials but displayed a limited therapeutic index. A new derivative of irofulven was prepared by reacting hydroxyurea with irofulven under acidic conditions. Acetylation of this new compound with acetic anhydride produced a second derivative. Both of these new derivatives displayed significant antitumor activity in vitro and in vivo comparable to or exceeding that of irofulven. Copyright © 2016 Elsevier Ltd. All rights reserved.

Automatic extraction of forward stroke volume using dynamic 11C-acetate PET/CT

DEFF Research Database (Denmark)

Harms, Hans; Tolbod, Lars Poulsen; Hansson, Nils Henrik

Objectives: Dynamic PET with 11C-acetate can be used to quantify myocardial blood flow and oxidative metabolism, the latter of which is used to calculate myocardial external efficiency (MEE). Calculation of MEE requires forward stroke volume (FSV) data. FSV is affected by cardiac loading conditions......, potentially introducing bias if measured with a separate modality. The aim of this study was to develop and validate methods for automatically extracting FSV directly from the dynamic PET used for measuring oxidative metabolism. Methods: 16 subjects underwent a dynamic 27 min PET scan on a Siemens Biograph...... TruePoint 64 PET/CT scanner after bolus injection of 399±27 MBq of 11C-acetate. The LV-aortic time-activity curve (TAC) was extracted automatically from dynamic PET data using cluster analysis. The first-pass peak was derived by automatic extrapolation of the down-slope of the TAC. FSV...

Heterotrophic and mixotrophic growth of Micractinium pusillum Fresenius in the presence of acetate and glucose: effect of light and acetate gradient concentration.

Science.gov (United States)

Bouarab, L; Dauta, A; Loudiki, M

2004-06-01

The main objective of this study was to determine the importance of secondary mechanism of organic carbon utilization (mixotrophic and heterotrophic modes) in addition to CO2 fixation (photoautotrophic mode) in the green alga, Micractinium pusillum Fresenius (chlorophyta), isolated from a waste stabilization pond. The growth was studied in the presence of acetate and glucose. The incorporation rate of 14C- acetate was measured in the light and in the dark at different concentrations. Finally, in order to underline the role of photosynthesis and respiration processes in the acetate assimilation, the effect of two specific metabolic inhibitors, a specific inhibitor of photosystem II (DCMU) and an uncoupler respiratory (DNP), has been studied. The obtained results showed that M. pusillum grows in the presence of organic substrates, i.e., glucose and acetate, in the light (mixotrophic growth) as well as in the dark (Heterotrophic growth). The growth was much more important in the light than in the dark and more in the presence of glucose than of acetate. In the light, the presence of acetate led to a variation of growth parameters mumax, iotaopt, and beta. The effect of acetate gradient on the growth of the microalga was severe as soon as its concentration in the medium was higher. The acetate uptake followed a Michaelis-Menten kinetic in the light as well as in the dark. The capacity of assimilation was slightly higher in the dark. The utilization of DNP and DCMU indicates that acetate incorporation is an active process depending on both anabolic (photosynthesis) and catabolic (respiration) metabolisms, corroborating the model of the Michaelis-Menten kinetic.

Syntheses of DNA adducts of two heterocyclic amines, 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeA alpha C) and 2-amino-9H-pyrido[2,3-b]indole (A alpha C) and identification of DNA adducts in organs from rats dosed with MeA alpha C

DEFF Research Database (Denmark)

Frederiksen, Hanne; Frandsen, Henrik Lauritz; Pfau, W.

2004-01-01

2-Amino-3-methyl-9H-pyrido[2,3-b]indole (MeAalphaC) and 2-amino-3-methyl-9H-pyrido[2,3-b]indole (AalphaC) are mutagenic and carcinogenic heterocyclic amines formed during ordinary cooking. MeAalphaC and AalphaC are activated to mutagenic metabolites by cytochrome P450-mediated N-oxidation...... by reaction of the parent amines with acetylated guanine N3-oxide. N-2-OH-MeAalphaC and N-2-OH-AalphaC reacted with calf thymus DNA after addition of acetic anhydride. P-32-postlabelling analysis of modified DNA showed one major adduct co-migrating with N-2-(3',5'-diphospho-2'-deoxyguanosin-8-yl...

Amino acid alphabet reduction preserves fold information contained in contact interactions in proteins.

Science.gov (United States)

Solis, Armando D

2015-12-01

To reduce complexity, understand generalized rules of protein folding, and facilitate de novo protein design, the 20-letter amino acid alphabet is commonly reduced to a smaller alphabet by clustering amino acids based on some measure of similarity. In this work, we seek the optimal alphabet that preserves as much of the structural information found in long-range (contact) interactions among amino acids in natively-folded proteins. We employ the Information Maximization Device, based on information theory, to partition the amino acids into well-defined clusters. Numbering from 2 to 19 groups, these optimal clusters of amino acids, while generated automatically, embody well-known properties of amino acids such as hydrophobicity/polarity, charge, size, and aromaticity, and are demonstrated to maintain the discriminative power of long-range interactions with minimal loss of mutual information. Our measurements suggest that reduced alphabets (of less than 10) are able to capture virtually all of the information residing in native contacts and may be sufficient for fold recognition, as demonstrated by extensive threading tests. In an expansive survey of the literature, we observe that alphabets derived from various approaches-including those derived from physicochemical intuition, local structure considerations, and sequence alignments of remote homologs-fare consistently well in preserving contact interaction information, highlighting a convergence in the various factors thought to be relevant to the folding code. Moreover, we find that alphabets commonly used in experimental protein design are nearly optimal and are largely coherent with observations that have arisen in this work. © 2015 Wiley Periodicals, Inc.

An Examination of the Carbon Isotope Effects Associated with Amino Acid Biosynthesis

Science.gov (United States)

Scott, James H.; O'Brien, Diane M.; Emerson, David; Sun, Henry; McDonald, Gene D.; Salgado, Antonio; Fogel, Marilyn L.

2006-12-01

Stable carbon isotope ratios (δ13C) were determined for alanine, proline, phenylalanine, valine, leucine, isoleucine, aspartate (aspartic acid and asparagine), glutamate (glutamic acid and glutamine), lysine, serine, glycine, and threonine from metabolically diverse microorganisms. The microorganisms examined included fermenting bacteria, organotrophic, chemolithotrophic, phototrophic, methylotrophic, methanogenic, acetogenic, acetotrophic, and naturally occurring cryptoendolithic communities from the Dry Valleys of Antarctica. Here we demonstrated that reactions involved in amino acid biosynthesis can be used to distinguish amino acids formed by life from those formed by nonbiological processes. The unique patterns of δ13C imprinted by life on amino acids produced a biological bias. We also showed that, by applying discriminant function analysis to the δ13C value of a pool of amino acids formed by biological activity, it was possible to identify key aspects of intermediary carbon metabolism in the microbial world. In fact, microorganisms examined in this study could be placed within one of three metabolic groups: (1) heterotrophs that grow by oxidizing compounds containing three or more carbon-to-carbon bonds (fermenters and organotrophs), (2) autotrophs that grow by taking up carbon dioxide (chemolitotrophs and phototrophs), and (3) acetoclastic microbes that grow by assimilation of formaldehyde or acetate (methylotrophs, methanogens, acetogens, and acetotrophs). Furthermore, we demonstrated that cryptoendolithic communities from Antarctica grouped most closely with the autotrophs, which indicates that the dominant metabolic pathways in these communities are likely those utilized for CO2 fixation. We propose that this technique can be used to determine the dominant metabolic types in a community and reveal the overall flow of carbon in a complex ecosystem.

Ulipristal acetate versus placebo for fibroid treatment before surgery.

Science.gov (United States)

Donnez, Jacques; Tatarchuk, Tetyana F; Bouchard, Philippe; Puscasiu, Lucian; Zakharenko, Nataliya F; Ivanova, Tatiana; Ugocsai, Gyula; Mara, Michal; Jilla, Manju P; Bestel, Elke; Terrill, Paul; Osterloh, Ian; Loumaye, Ernest

2012-02-02

The efficacy and safety of oral ulipristal acetate for the treatment of symptomatic uterine fibroids before surgery are uncertain. We randomly assigned women with symptomatic fibroids, excessive uterine bleeding (a score of >100 on the pictorial blood-loss assessment chart [PBAC, an objective assessment of blood loss, in which monthly scores range from 0 to >500, with higher numbers indicating more bleeding]) and anemia (hemoglobin level of ≤10.2 g per deciliter) to receive treatment for up to 13 weeks with oral ulipristal acetate at a dose of 5 mg per day (96 women) or 10 mg per day (98 women) or to receive placebo (48 women). All patients received iron supplementation. The coprimary efficacy end points were control of uterine bleeding (PBAC score of <75) and reduction of fibroid volume at week 13, after which patients could undergo surgery. At 13 weeks, uterine bleeding was controlled in 91% of the women receiving 5 mg of ulipristal acetate, 92% of those receiving 10 mg of ulipristal acetate, and 19% of those receiving placebo (P<0.001 for the comparison of each dose of ulipristal acetate with placebo). The rates of amenorrhea were 73%, 82%, and 6%, respectively, with amenorrhea occurring within 10 days in the majority of patients receiving ulipristal acetate. The median changes in total fibroid volume were -21%, -12%, and +3% (P=0.002 for the comparison of 5 mg of ulipristal acetate with placebo, and P=0.006 for the comparison of 10 mg of ulipristal acetate with placebo). Ulipristal acetate induced benign histologic endometrial changes that had resolved by 6 months after the end of therapy. Serious adverse events occurred in one patient during treatment with 10 mg of ulipristal acetate (uterine hemorrhage) and in one patient during receipt of placebo (fibroid protruding through the cervix). Headache and breast tenderness were the most common adverse events associated with ulipristal acetate but did not occur significantly more frequently than with placebo

Improving ethanol yield in acetate-reducing Saccharomyces cerevisiae by cofactor engineering of 6-phosphogluconate dehydrogenase and deletion of ALD6.

Science.gov (United States)

Papapetridis, Ioannis; van Dijk, Marlous; Dobbe, Arthur P A; Metz, Benjamin; Pronk, Jack T; van Maris, Antonius J A

2016-04-26

Acetic acid, an inhibitor of sugar fermentation by yeast, is invariably present in lignocellulosic hydrolysates which are used or considered as feedstocks for yeast-based bioethanol production. Saccharomyces cerevisiae strains have been constructed, in which anaerobic reduction of acetic acid to ethanol replaces glycerol formation as a mechanism for reoxidizing NADH formed in biosynthesis. An increase in the amount of acetate that can be reduced to ethanol should further decrease acetic acid concentrations and enable higher ethanol yields in industrial processes based on lignocellulosic feedstocks. The stoichiometric requirement of acetate reduction for NADH implies that increased generation of NADH in cytosolic biosynthetic reactions should enhance acetate consumption. Replacement of the native NADP(+)-dependent 6-phosphogluconate dehydrogenase in S. cerevisiae by a prokaryotic NAD(+)-dependent enzyme resulted in increased cytosolic NADH formation, as demonstrated by a ca. 15% increase in the glycerol yield on glucose in anaerobic cultures. Additional deletion of ALD6, which encodes an NADP(+)-dependent acetaldehyde dehydrogenase, led to a 39% increase in the glycerol yield compared to a non-engineered strain. Subsequent replacement of glycerol formation by an acetate reduction pathway resulted in a 44% increase of acetate consumption per amount of biomass formed, as compared to an engineered, acetate-reducing strain that expressed the native 6-phosphogluconate dehydrogenase and ALD6. Compared to a non-acetate reducing reference strain under the same conditions, this resulted in a ca. 13% increase in the ethanol yield on glucose. The combination of NAD(+)-dependent 6-phosphogluconate dehydrogenase expression and deletion of ALD6 resulted in a marked increase in the amount of acetate that was consumed in these proof-of-principle experiments, and this concept is ready for further testing in industrial strains as well as in hydrolysates. Altering the cofactor

An OmpA Family Protein, a Target of the GinI/GinR Quorum-Sensing System in Gluconacetobacter intermedius, Controls Acetic Acid Fermentation▿ †

Science.gov (United States)

Iida, Aya; Ohnishi, Yasuo; Horinouchi, Sueharu

2008-01-01

Via N-acylhomoserine lactones, the GinI/GinR quorum-sensing system in Gluconacetobacter intermedius NCI1051, a gram-negative acetic acid bacterium, represses acetic acid and gluconic acid fermentation. Two-dimensional polyacrylamide gel electrophoretic analysis of protein profiles of strain NCI1051 and ginI and ginR mutants identified a protein that was produced in response to the GinI/GinR regulatory system. Cloning and nucleotide sequencing of the gene encoding this protein revealed that it encoded an OmpA family protein, named GmpA. gmpA was a member of the gene cluster containing three adjacent homologous genes, gmpA to gmpC, the organization of which appeared to be unique to vinegar producers, including “Gluconacetobacter polyoxogenes.” In addition, GmpA was unique among the OmpA family proteins in that its N-terminal membrane domain forming eight antiparallel transmembrane β-strands contained an extra sequence in one of the surface-exposed loops. Transcriptional analysis showed that only gmpA of the three adjacent gmp genes was activated by the GinI/GinR quorum-sensing system. However, gmpA was not controlled directly by GinR but was controlled by an 89-amino-acid protein, GinA, a target of this quorum-sensing system. A gmpA mutant grew more rapidly in the presence of 2% (vol/vol) ethanol and accumulated acetic acid and gluconic acid in greater final yields than strain NCI1051. Thus, GmpA plays a role in repressing oxidative fermentation, including acetic acid fermentation, which is unique to acetic acid bacteria and allows ATP synthesis via ethanol oxidation. Consistent with the involvement of gmpA in oxidative fermentation, its transcription was also enhanced by ethanol and acetic acid. PMID:18487322

Structure Determination of Cisplatin-Amino Acid Analogues by Infrared Multiple Photon Dissociation Action Spectroscopy

Science.gov (United States)

He, Chenchen; Bao, Xun; Zhu, Yanlong; Strobehn, Stephen; Kimutai, Bett; Nei, Y.-W.; Chow, C. S.; Rodgers, M. T.; Gao, Juehan; Oomens, J.

2015-06-01

To gain a better understanding of the binding mechanism and assist in the optimization of relevant drug and chemical probe design, both experimental and theoretical studies were performed on a series of amino acid-linked cisplatin derivatives, including glycine-, lysine-, and ornithine-linked cisplatin, Gplatin, Kplatin, and Oplatin, respectively. Cisplatin, the first FDA-approved platinum-based anticancer drug, has been widely used in cancer chemotherapy. Its pharmacological mechanism has been identified as its ability to coordinate to genomic DNA, and guanine is its major target. In previous reports, cisplatin was successfully utilized as a chemical probe to detect solvent accessible sites in ribosomal RNA (rRNA). Among the amino-acid-linked cisplatin derivatives, Oplatin exhibits preference for adenine over guanine. The mechanism behind its different selectivity compared to cisplatin may relate to its potential of forming a hydrogen bond between the carboxylate group in Pt (II) complex and the 6-amino moiety of adenosine stabilizes A-Oplatin products. Tandem mass spectrometry analysis also indicates that different coordination sites of Oplatin on adenosine affect glycosidic bond stability. Infrared multiple photon dissociation (IRMPD) action spectroscopy experiments were performed on all three amino acid-linked cisplatin to characterize their structures. An extensive theoretical study has been performed on Gplatin to guide the selection of the most effective theory and basis set based on its geometric information. The results for Gplatin provide the foundation for characterization of the more complex amino acid-linked cisplatin derivatives, Oplatin and Kplatin. Structural and energetic information elucidated for these compounds, particularly Oplatin reveal the reason for its alternative selectivity compared to cisplatin.

Survival of Acetate in Biodegraded Stream Water DOM: New Insights Based on NMR Spectroscopy

Science.gov (United States)

Whitty, S.; Waggoner, D. C.; Bowen, J. C.; Cory, R. M.; Kaplan, L.; Hatcher, P.

2017-12-01

DOM is a complex chemical mixture of high- (HMW) and low-molecular-weight (LMW) organic molecules that serve as the primary energy sources for heterotrophic bacteria in freshwater environments. However, there are still large uncertainties on the composition of DOM that is labile and thus rapidly metabolized. The current thinking is that labile DOM is primarily composed of monosaccharides, amino acids, and other LMW organic acids such as formic, acetic, or propionic among others, although some humic substances also are biologically labile. To test the contribution of LMW organic acids to the labile fraction of DOM, freshwater samples were collected from five streams within the Rio Tempisquito watershed in Costa Rica and subjected to differing degrees of biodegradation using a series of plug-flow bioreactors with residence times ranging from 0.5-150 min. Varying the residence times of bioreactors allows for separation and identification of labile from less labile to more recalcitrant DOM. The stream water fed into the bioreactors had DOC concentrations that ranged from 0.7-1.2 ppm C and the GF/F-filtered stream water as well as the bioreactor effluents were analyzed directly without pre-treatment using proton nuclear magnetic resonance spectroscopy (1H NMR). Small molecules dominated the 1H NMR spectra with the greatest changes, as a function of bioreactor residence time, in the carbohydrate, terminal methyl, and long-chain methylene structures. In contrast, acetate remained relatively constant after 150 min of bioreactor residence time, thus raising the question of why this inherently labile volatile fatty acid was not consumed by stream microbes colonizing bioreactors that otherwise metabolized approximately 35% of the total dissolved organic carbon present in the stream water. We suggest that acetate may resist biodegradation because it is complexed strongly with inorganic cations.

New derivatives of 3,4-dihydroisoquinoline-3-carboxylic acid with free-radical scavenging, D-amino acid oxidase, acetylcholinesterase and butyrylcholinesterase inhibitory activity.

Science.gov (United States)

Solecka, Jolanta; Guśpiel, Adam; Postek, Magdalena; Ziemska, Joanna; Kawęcki, Robert; Lęczycka, Katarzyna; Osior, Agnieszka; Pietrzak, Bartłomiej; Pypowski, Krzysztof; Wyrzykowska, Agata

2014-09-30

A series of 3,4-dihydroisoquinoline-3-carboxylic acid derivatives were synthesised and tested for their free-radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl radical (DPPH·), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical (ABTS·+), superoxide anion radical (O2·-) and nitric oxide radical (·NO) assays. We also studied d-amino acid oxidase (DAAO), acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitory activity. Almost each of newly synthesised compounds exhibited radical scavenging capabilities. Moreover, several compounds showed moderate inhibitory activities against DAAO, AChE and BuChE. Compounds with significant free-radical scavenging activity may be potential candidates for therapeutics used in oxidative-stress-related diseases.

Synthesis and Anticancer Activity of Some New Pyrazolo[3,4-d]pyrimidin-4-one Derivatives

Directory of Open Access Journals (Sweden)

Khaled R. A. Abdellatif

2014-03-01

Full Text Available 3,6-Dimethyl-1-phenyl-1H-pyrazolo[3,4-d][1,3]oxazin-4-one (3 was prepared by hydrolysis of ethyl 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1 to afford the corresponding carboxylic acid 2, which was reacted with acetic anhydride to give 3. The pyrazolo[3,4-d][1,3]oxazin-4-one 3 was reacted with hydroxylamine hydrochloride, urea, thiourea, thiosemicarbazide, phenylhydrazine and aromatic amines to afford the corresponding pyrazolo[3,4-d]pyrimidin-4-ones 4, 5a,b, 6, 7, 8a–e, respectively. Condensation of pyrazoloxazine derivative 3 with 99% hydrazine hydrate afforded the 5-aminopyrazolo[3,4-d] pyrimidine derivative 9. Coupling of 9 with aromatic aldehydes yielded a series of 3,6-dimethyl-5-(4-substitutedbenzylideneamino-1-phenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin- 4-ones 10a–e. The new compounds were tested for their antitumor activity on the MCF-7 human breast adenocarcinoma cell line. Almost all the tested compounds revealed antitumor activity, especially 3,6-dimethyl-5-(4-nitrobenzylideneamino-1-phenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one (10e which displayed the most potent inhibitory activity with a half maximal inhibitory concentration (IC50 of 11 µM.

Effect of fermentation period on the organic acid and amino acid contents of Ogiri from castor oil bean seeds

Directory of Open Access Journals (Sweden)

Ojinnaka, M-T. C.

2013-01-01

Full Text Available Aims: To monitor the changes in the concentration of organic acid and amino acid contents during the fermentation of castor oil bean seed into ogiri.Methodology and results: In this study, ogiri, a Nigerian fermented food condiment was prepared from castor oil bean using Bacillus subtilis as a monoculture starter for the production of three different fermented castor oil bean condiment samples: B1 (0% NaCl/lime, B2 (2% NaCl, B3 (3% lime. Variations in the composition of the castor oil bean with fermentation over 96 h periods were evaluated for organic acid and amino acid contents using High Performance Liquid Chromatography. Organic acids were detected in the fermented castor oil bean samples as fermentation period increased to 96 h. Organic acids identified were oxalic, citric, tartaric, malic, succinic, lactic, formic, acetic, propionic and butyric acids. The lactic acid contents in sample B1 (0% NaCl/lime decreased initially and then increased as the fermentation period progressed. The value at 96 h fermentation was 1.336 µg/mL as against 0.775 µg/mL at 0 h fermentation. Sample B3 (3% lime had lactic acid content that increased as fermentation period increased with lactic acid content of 1.298 µg/mL at 96 h fermentation. The acetic acid content of sample B1 increased as fermentation progressed and at 96 h fermentation, its value was 1.204 µg/mL while those of B2 and B3 were 0.677 µg/mL and 1.401 µg/mL respectively. The three fermented castor oil bean samples also contained sufficient amount of amino acids. Sample B1 had the highest values in isoleucine glycine and histidine with values 1.382 µg/mL, 0.814 µg/mL and 1.022 µg/mL respectively while sample B2 had the highest value in leucine content with 0.915 µg/mL at 96 h fermentation, closely followed by sample B3 and B1 with 0.798 µg/mL and 0.205 µg/mL respectively. The results of amino acid analysis indicated a high concentration of all amino acids at 96 h of fermentation

Photodissociation spectroscopy of the Mg+-acetic acid complex

Science.gov (United States)

Abate, Yohannes; Kleiber, P. D.

2006-11-01

We have studied the structure and photodissociation of Mg+-acetic acid clusters. Ab initio calculations suggest four relatively strongly bound ground state isomers for the [MgC2H4O2]+ complex. These isomers include the cis and trans forms of the Mg+-acetic acid association complex with Mg+ bonded to the carbonyl O atom of acetic acid, the Mg+-acetic acid association complex with Mg+ bonded to the hydroxyl O atom of acetic acid, or to a Mg+-ethenediol association complex. Photodissociation through the Mg+-based 3p←3s absorption bands in the near UV leads to direct (nonreactive) and reactive dissociation products: Mg+, MgOH+, Mg(H2O )+, CH3CO+, and MgCH3+. At low energies the dominant reactive quenching pathway is through dehydration to Mg(H2O)+, but additional reaction channels involving C-H and C-C bond activation are also open at higher energies.

X-ray diffraction studies of chitosan acetate-based polymer electrolytes

International Nuclear Information System (INIS)

Osman, Z.; Ibrahim, Z.A.; Abdul Kariem Arof

2002-01-01

Chitosan is the product when partially deacetylated chitin dissolves in dilute acetic acid. This paper presents the x-ray diffraction patterns of chitosan acetate, plasticised chitosan acetate and plasticised-salted chitosan acetate films. The results show that the chitosan acetate based polymer electrolyte films are not completely amorphous but it is partially crystalline. X-ray diffraction study also confirms the occurrence of the complexation between chitosan and the salt and the interaction between salt and plasticizer. The salt-chitosan interaction is clearly justified by infrared spectroscopy. (Author)

Synthesis, antifungal evaluation and in silico study of novel Schiff bases derived from 4-amino-5(3,5-dimethoxy-phenyl-4H-1,2,4-triazol-3-thiol

Directory of Open Access Journals (Sweden)

N.S. Hari Narayana Moorthy

2017-05-01

Full Text Available A novel series of Schiff bases based on of 4-amino-5-(3,5-dimethoxy-phenyl-4H-1,2,4-triazol-3-thiol scaffold was prepared by heating thiocarbohydrazide and 3,5,-dimethoxy benzoic acid at the temperature above its meting point, and subsequently, treating with substituted benzaldehydes. The chemical constituents in the synthesized compounds were confirmed by IR, Mass, 1H NMR spectroscopy and elemental analysis and the antifungal activity was evaluated against Candida albicans. The structure activity relationship analysis shows that the chloride substituted derivatives possess promising activity in micromolar concentration and also the hydroxy phenyl derivatives exhibited considerable activity at 128 μg/ml. But other compounds with amino, furan and methoxy substitutions did not show antifungal activity till the concentration of 512 μg/ml. In silico pharmacokinetic prediction shows that all the compounds obeyed Lipinski rule of 5 and are free of toxicity and metabolically stable. Pharmacophore analysis revealed that the aromatic/hydrophobic and aromatic/acceptor/donor features in the compounds are essential for the activity. The predicted cardiotoxicity (hERG and lethal effect of the synthesized compounds will permit us to carry out further in vitro and in vivo toxicity studies.

New insights into the metabolism of aspartate-family amino acids in plant seeds.

Science.gov (United States)

Wang, Wenyi; Xu, Mengyun; Wang, Guoping; Galili, Gad

2018-02-05

Aspartate-family amino acids. Aspartate (Asp)-family pathway, via several metabolic branches, leads to four key essential amino acids: Lys, Met, Thr, and Ile. Among these, Lys and Met have received the most attention, as they are the most limiting amino acid in cereals and legumes crops, respectively. The metabolic pathways of these four essential amino acids and their interactions with regulatory networks have been well characterized. Using this knowledge, extensive efforts have been devoted to augmenting the levels of these amino acids in various plant organs, especially seeds, which serve as the main source of human food and livestock feed. Seeds store a number of storage proteins, which are utilized as nutrient and energy resources. Storage proteins are composed of amino acids, to guarantee the continuation of plant progeny. Thus, understanding the seed metabolism, especially with respect to the accumulation of aspartate-derived amino acids Lys and Met, is a crucial factor for sustainable agriculture. In this review, we summarized the Asp-family pathway, with some new examples of accumulated Asp-family amino acids, particularly Lys and Met, in plant seeds. We also discuss the recent advances in understanding the roles of Asp-family amino acids during seed development.

Integrated phospholipidomics and transcriptomics analysis of Saccharomyces cerevisiae with enhanced tolerance to a mixture of acetic acid, furfural, and phenol

Science.gov (United States)

A mixture of acetic acid, furfural and phenol (AFP), three representative lignocellulose derived inhibitors, significantly inhibited the growth and bioethanol production of Saccharomyces cerevisiae. In order to uncover mechanisms behind the enhanced tolerance of an inhibitor-tolerant S.cerevisiae s...

Growth of Chlamydomonas reinhardtii in acetate-free medium when co-cultured with alginate-encapsulated, acetate-producing strains of Synechococcus sp. PCC 7002.

Science.gov (United States)

Therien, Jesse B; Zadvornyy, Oleg A; Posewitz, Matthew C; Bryant, Donald A; Peters, John W

2014-01-01

The model alga Chlamydomonas reinhardtii requires acetate as a co-substrate for optimal production of lipids, and the addition of acetate to culture media has practical and economic implications for algal biofuel production. Here we demonstrate the growth of C. reinhardtii on acetate provided by mutant strains of the cyanobacterium Synechococcus sp. PCC 7002. Optimal growth conditions for co-cultivation of C. reinhardtii with wild-type and mutant strains of Synechococcus sp. 7002 were established. In co-culture, acetate produced by a glycogen synthase knockout mutant of Synechococcus sp. PCC 7002 was able to support the growth of a lipid-accumulating mutant strain of C. reinhardtii defective in starch production. Encapsulation of Synechococcus sp. PCC 7002 using an alginate matrix was successfully employed in co-cultures to limit growth and maintain the stability. The ability of immobilized strains of the cyanobacterium Synechococcus sp. PCC 7002 to produce acetate at a level adequate to support the growth of lipid-accumulating strains of C. reinhartdii offers a potentially practical, photosynthetic alternative to providing exogenous acetate into growth media.

Natural zinniol derivatives from Alternaria tagetica. Isolation, synthesis, and structure-activity correlation.

Science.gov (United States)

Gamboa-Angulo, M Marcela; Escalante-Erosa, Fabiola; García-Sosa, Karlina; Alejos-González, Fátima; Delgado-Lamas, Guillermo; Peña-Rodríguez, Luis M

2002-02-27

Two novel phytotoxins, 8-zinniol methyl ether (5) and 8-zinniol acetate (6), in addition to 6-(3',3'-dimethylallyloxy)-4-methoxy-5-methylphthalide (2), 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methylphthalide (3), and the novel metabolites 8-zinniol 2-(phenyl)ethyl ether (4) and 7-zinniol acetate (7) have been identified as natural zinniol derivatives from the organic crude extract of Alternaria tagetica culture filtrates. Using zinniol as the starting material, phytotoxin 5 was synthesized, together with a number of synthetic intermediates (8-13). Both natural and synthetic zinniol derivatives were evaluated in the leaf-spot bioassay against marigold leaves (Tagetes erecta).

Acetic acid extraction from aqueous solutions using fatty acids

NARCIS (Netherlands)

IJmker, H.M.; Gramblicka, M.; Kersten, Sascha R.A.; van der Ham, Aloysius G.J.; Schuur, Boelo

2014-01-01

A major challenge for production of acetic acid via bio-based routes is cost-effective concentration and purification of the acetic acid from the aqueous solutions, for which liquid–liquid extraction is a possible method. A main challenge in extraction of acetic acid from dilute aqueous solutions is

Isotope-labelled folic acid derivatives

International Nuclear Information System (INIS)

Lewin, N.; Wong, E.T.

1976-01-01

The suggestion deals with the production of folic acid derivatives suitable as indicators or tracers for analyses of serum folates. These folic acid derivatives contain folic acid which is bound by one or both carboxyl groups to the amino nitrogen of compounds such as, e.g., tyramine, glycyl tyrosine, tyrosine, or the methyl ester of tyrosine. The derivative obtained can be substituted by a gamma emitter, e.g. the iodine isotope I 125. The radioactive derivative is used in the method for the competitive protein bonding to determine endogenic folates in the serum. (UWI) [de

Production of a new D-amino acid oxidase from the fungus Fusarium oxysporum.

Science.gov (United States)

Gabler, M; Fischer, L

1999-08-01

The fungus Fusarium oxysporum produced a D-amino acid oxidase (EC 1. 4.3.3) in a medium containing glucose as the carbon and energy source and ammonium sulfate as the nitrogen source. The specific D-amino acid oxidase activity was increased up to 12.5-fold with various D-amino acids or their corresponding derivatives as inducers. The best inducers were D-alanine (2.7 microkat/g of dry biomass) and D-3-aminobutyric acid (2.6 microkat/g of dry biomass). The addition of zinc ions was necessary to permit the induction of peroxisomal D-amino acid oxidase. Bioreactor cultivations were performed on a 50-liter scale, yielding a volumetric D-amino acid oxidase activity of 17 microkat liter(-1) with D-alanine as an inducer. Under oxygen limitation, the volumetric activity was increased threefold to 54 microkat liter(-1) (3,240 U liter(-1)).

Heterotrophic utilization of acetate and glucose in Swartvlei, South Africa

International Nuclear Information System (INIS)

Robarts, R.D.

1979-01-01

The utilization of dissolved organic compounds in Swartvlei was measured by the addition of single concentrations of 14 C-labelled acetate and glucose to water samples. The results indicated acetate uptake was greatest in the aerobic zone while glucose was predominantly utilized in the anaerobic zone. With the exception of two months, integral glucose uptake was usually greater than the uptake of acetate. In August and September 1971 acetate was indicated as being utilized predominantly by flagellates and in December 1971 by dinoflagellates. During the remainder of the study, bacteria were assumed to be responsible for the uptake of acetate. The extensive weed beds which surround the upper reaches of Swartvlei may be a major source of acetate and glucose in the pelagic water column

Thermodynamic studies on corrosion inhibition of aqueous solutions of amino/carboxylic acids toward copper by EMF measurement

International Nuclear Information System (INIS)

Spah, Manjula; Spah, Dal Chand; Deshwal, Balraj; Lee, Seungmoon; Chae, Yoon-Keun; Park, Jin Won

2009-01-01

Electromotive force (E) measurements were made on an electrochemical cell [Cu x Hg|CuCl 2 (m) in a solvent S|AgCl-Ag] (where S is a dilute aqueous solution (0.01 m) of amino acid (glycine, alanine, methionine and glutamic acid) or aliphatic carboxylic acid (formic acid, acetic acid, n-butyric acid and glutaric acid)) at 30 deg. C. These measured E values were used to compute the dissociation constants (K 1 and K 2 ) and the degree of dissociation (α 1 and α 2 ) by iterative procedures. The standard cell potential (E o ) and the mean activity coefficient (γ ± ) of CuCl 2 were also determined. The E o data were next used to evaluate the Gibbs energy of transfer (ΔG tr 0 ) of CuCl 2 from water to dilute aqueous solutions of the amino/carboxylic acids. The negative ΔG tr 0 values suggested that these acids act as potential corrosion inhibitors. The magnitudes of ΔG tr 0 values show that the amino acids act as better corrosion inhibitors towards copper than the aliphatic carboxylic acids.

Enhanced Bio-hydrogen Production from Protein Wastewater by Altering Protein Structure and Amino Acids Acidification Type

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Xiao, Naidong; Chen, Yinguang; Chen, Aihui; Feng, Leiyu

2014-01-01

Enhanced bio-hydrogen production from protein wastewater by altering protein structure and amino acids acidification type via pH control was investigated. The hydrogen production reached 205.2 mL/g-protein when protein wastewater was pretreated at pH 12 and then fermented at pH 10. The mechanism studies showed that pH 12 pretreatment significantly enhanced protein bio-hydrolysis during the subsequent fermentation stage as it caused the unfolding of protein, damaged the protein hydrogen bonding networks, and destroyed the disulfide bridges, which increased the susceptibility of protein to protease. Moreover, pH 10 fermentation produced more acetic but less propionic acid during the anaerobic fermentation of amino acids, which was consistent with the theory of fermentation type affecting hydrogen production. Further analyses of the critical enzymes, genes, and microorganisms indicated that the activity and abundance of hydrogen producing bacteria in the pH 10 fermentation reactor were greater than those in the control. PMID:24495932

Enhanced bio-hydrogen production from protein wastewater by altering protein structure and amino acids acidification type.

Science.gov (United States)

Xiao, Naidong; Chen, Yinguang; Chen, Aihui; Feng, Leiyu

2014-02-05

Enhanced bio-hydrogen production from protein wastewater by altering protein structure and amino acids acidification type via pH control was investigated. The hydrogen production reached 205.2 mL/g-protein when protein wastewater was pretreated at pH 12 and then fermented at pH 10. The mechanism studies showed that pH 12 pretreatment significantly enhanced protein bio-hydrolysis during the subsequent fermentation stage as it caused the unfolding of protein, damaged the protein hydrogen bonding networks, and destroyed the disulfide bridges, which increased the susceptibility of protein to protease. Moreover, pH 10 fermentation produced more acetic but less propionic acid during the anaerobic fermentation of amino acids, which was consistent with the theory of fermentation type affecting hydrogen production. Further analyses of the critical enzymes, genes, and microorganisms indicated that the activity and abundance of hydrogen producing bacteria in the pH 10 fermentation reactor were greater than those in the control.

Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡

Science.gov (United States)

Vavříková, Eva; Gavezzotti, Paolo; Purchartová, Kateřina; Fuksová, Kateřina; Biedermann, David; Kuzma, Marek; Riva, Sergio; Křen, Vladimír

2015-01-01

A panel of lipases was screened for the selective acetylation and alcoholysis of silychristin and silychristin peracetate, respectively. Acetylation at primary alcoholic group (C-22) of silychristin was accomplished by lipase PS (Pseudomonas cepacia) immobilized on diatomite using vinyl acetate as an acetyl donor, whereas selective deacetylation of 22-O-acetyl silychristin was accomplished by Novozym 435 in methyl tert-butyl ether/n-butanol. Both of these reactions occurred without diastereomeric discrimination of silychristin A and B. Both of these enzymes were found to be capable to regioselective deacetylation of hexaacetyl silychristin to afford penta-, tetra- and tri-acetyl derivatives, which could be obtained as pure synthons for further selective modifications of the parent molecule. PMID:26016503

Kinetic Modelling and Experimental Study of Small Esters: Methyl Acetate and Ethyl Acetate

KAUST Repository

Ahmed, Ahfaz; Mehl, Marco; Lokachari, Nitin; Nilsson, Elna J.K.; Konnov, Alexander A.; Wagnon, Scott W.; Pitz, William J.; Curran, Henry J.; Roberts, William L.; Sarathy, Mani

2017-01-01

A detailed chemical kinetic mechanism comprising methyl acetate and ethyl acetate has been developed based on the previous work by Westbrook et al. [1]. The newly developed kinetic mechanism has been updated with new reaction rates from recent theoretical studies. To validate this model, shock tube experiments measuring ignition delay time have been conducted at 15 & 30 bar and equivalence ratio 0.5, 1.0 and 2.0. Another set of experiments measuring laminar burning velocity was also performed on a heat flux burner at atmospheric pressure over wide range of equivalence ratios [~0.7-1.4]. The new mechanism shows significant improvement in prediction of experimental data over earlier model across the range of experiments.

Kinetic Modelling and Experimental Study of Small Esters: Methyl Acetate and Ethyl Acetate

KAUST Repository

Ahmed, Ahfaz

2017-12-14

A detailed chemical kinetic mechanism comprising methyl acetate and ethyl acetate has been developed based on the previous work by Westbrook et al. [1]. The newly developed kinetic mechanism has been updated with new reaction rates from recent theoretical studies. To validate this model, shock tube experiments measuring ignition delay time have been conducted at 15 & 30 bar and equivalence ratio 0.5, 1.0 and 2.0. Another set of experiments measuring laminar burning velocity was also performed on a heat flux burner at atmospheric pressure over wide range of equivalence ratios [~0.7-1.4]. The new mechanism shows significant improvement in prediction of experimental data over earlier model across the range of experiments.

2-Phenyl-tetrahydropyrimidine-4(1H-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

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Markus Nahrwold

2009-09-01

Full Text Available Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R-β2-homoaspartate.

Acetate causes alcohol hangover headache in rats.

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Christina R Maxwell

2010-12-01

Full Text Available The mechanism of veisalgia cephalgia or hangover headache is unknown. Despite a lack of mechanistic studies, there are a number of theories positing congeners, dehydration, or the ethanol metabolite acetaldehyde as causes of hangover headache.We used a chronic headache model to examine how pure ethanol produces increased sensitivity for nociceptive behaviors in normally hydrated rats.Ethanol initially decreased sensitivity to mechanical stimuli on the face (analgesia, followed 4 to 6 hours later by inflammatory pain. Inhibiting alcohol dehydrogenase extended the analgesia whereas inhibiting aldehyde dehydrogenase decreased analgesia. Neither treatment had nociceptive effects. Direct administration of acetate increased nociceptive behaviors suggesting that acetate, not acetaldehyde, accumulation results in hangover-like hypersensitivity in our model. Since adenosine accumulation is a result of acetate formation, we administered an adenosine antagonist that blocked hypersensitivity.Our study shows that acetate contributes to hangover headache. These findings provide insight into the mechanism of hangover headache and the mechanism of headache induction.

SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE

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Muhammad Idham Darussalam Mardjan

2012-02-01

Full Text Available Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.

Poly(amino acid) functionalized maghemite and gold nanoparticles

International Nuclear Information System (INIS)

Perego, Davide; Manuel Domínguez-Vera, José; Gálvez, Natividad; Masciocchi, Norberto; Guagliardi, Antonietta

2013-01-01

Bimodal MRI/OI imaging probes are of great interest in nanomedicine. Although many organic polymers have been studied thoroughly for in vivo applications, reports on the use of poly(amino acid)s as coating polymers are scarce. In this paper, poly-(d-glutamic acid, d-lysine) (PGL) has been used for coating maghemite and gold nanoparticles. An advantage of this flexible and biocompatible polymer is that, once anchored to the nanoparticle surface, dangling lysine amino groups are available for the incorporation of new functionalities. As an example, Alexa Fluor derivatives have been attached to PGL-coated maghemite nanoparticles to obtain magnetic/fluorescent materials. These dual-property materials could be used as bimodal MRI/OI probes for in vivo imaging. (paper)

Addressing Cellulose Acetate Microfilm from a British Library perspective

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Helen Shenton

2005-08-01

Full Text Available This paper is about cellulose acetate microfilm from the British Library perspective. It traces how acetate microfilm became an issue for the British Library and describes cellulose acetate deterioration. This is followed by details of what has already been done about the situation and what action is planned for the future.

Kinetics of Ethyl Acetate Synthesis Catalyzed by Acidic Resins

Science.gov (United States)

Antunes, Bruno M.; Cardoso, Simao P.; Silva, Carlos M.; Portugal, Ines

2011-01-01

A low-cost experiment to carry out the second-order reversible reaction of acetic acid esterification with ethanol to produce ethyl acetate is presented to illustrate concepts of kinetics and reactor modeling. The reaction is performed in a batch reactor, and the acetic acid concentration is measured by acid-base titration versus time. The…

Synthesis of 4-Methylene-2-cyclohexenones and Their Aromatization Reaction toward para-Methoxylmethyl Anisole Derivatives

International Nuclear Information System (INIS)

Lee, Jeong Mi; Lee, Ka Young; Kim, Jae Nyoung

2004-01-01

We and other groups have reported the selective introduction of nucleophiles at the secondary benzylic position of the Baylis-Hillman acetates via the corresponding DABCO salts. Thus, we envisioned that we could prepare 4-methylene- 2-cyclohexenone skeleton and para-methoxymethyl anisoles by combining the DABCO salt concept and the aromatization reaction with iodine in methanol. Suitably substituted anisoles are useful as the starting materials for the fragrances, dyes and pesticides, as antioxidants in oils and fats, or as stabilizers of plastics. Moreover, paramethoxymethyl anisoles have been used for the kinetic acetalization of diol or amino alcohol systems in the presence of DDQ5 during the synthesis of (+)-FR900482, taxotere side chain,5c cyclopropyl lactone oxylipins, and erythromycin A.

D-Amino acids incorporation in the frog skin-derived peptide esculentin-1a(1-21)NH2 is beneficial for its multiple functions.

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Di Grazia, Antonio; Cappiello, Floriana; Cohen, Hadar; Casciaro, Bruno; Luca, Vincenzo; Pini, Alessandro; Di, Y Peter; Shai, Yechiel; Mangoni, Maria Luisa

2015-12-01

Naturally occurring antimicrobial peptides (AMPs) represent promising future antibiotics. We have previously isolated esculentin-1a(1-21)NH2, a short peptide derived from the frog skin AMP esculentin-1a, with a potent anti-Pseudomonal activity. Here, we investigated additional functions of the peptide and properties responsible for these activities. For that purpose, we synthesized the peptide, as well as its structurally altered analog containing two D-amino acids. The peptides were then biophysically and biologically investigated for their cytotoxicity and immunomodulating activities. The data revealed that compared to the wild-type, the diastereomer: (1) is significantly less toxic towards mammalian cells, in agreement with its lower α-helical structure, as determined by circular dichroism spectroscopy; (2) is more effective against the biofilm form of Pseudomonas aeruginosa (responsible for lung infections in cystic fibrosis sufferers), while maintaining a high activity against the free-living form of this important pathogen; (3) is more stable in serum; (4) has a higher activity in promoting migration of lung epithelial cells, and presumably in healing damaged lung tissue, and (5) disaggregates and detoxifies the bacterial lipopolysaccharide (LPS), albeit less than the wild-type. Light scattering studies revealed a correlation between anti-LPS activity and the ability to disaggregate the LPS. Besides shedding light on the multifunction properties of esculentin-1a(1-21)NH2, the D-amino acid containing isomer may serve as an attractive template for the development of new anti-Pseudomonal compounds with additional beneficial properties. Furthermore, together with other studies, incorporation of D-amino acids may serve as a general approach to optimize the future design of new AMPs.

Identification of target genes to control acetate yield during aerobic fermentation with Saccharomyces cerevisiae.

Science.gov (United States)

Curiel, José Antonio; Salvadó, Zoel; Tronchoni, Jordi; Morales, Pilar; Rodrigues, Alda Joao; Quirós, Manuel; Gonzalez, Ramón

2016-09-15

Aerobic fermentation of grape must, leading to respiro-fermentative metabolism of sugars, has been proposed as way of reducing alcohol content in wines. Two factors limit the usefulness of Saccharomyces cerevisiae for this application, the Crabtree effect, and excess volatile acidity under aerobic conditions. This work aimed to explore the impact on ethanol acetate production of different S. cerevisiae strains deleted for genes previously related with the Crabtree phenotype. Recombinant strains were constructed on a wine industrial genetic background, FX10. All yeast strains, including FX10, showed respiro-fermentative metabolism in natural grape must under aerobic conditions, as well as a concomitant reduction in ethanol yield. This indicates that the Crabtree effect is not a major constrain for reaching relevant respiration levels in grape must. Indeed, only minor differences in ethanol yield were observed between the original and some of the recombinant strains. In contrast, some yeast strains showed a relevant reduction of acetic acid production. This was identified as a positive feature for the feasibility of alcohol level reduction by respiration. Reduced acetic acid production was confirmed by a thorough analysis of these and some additional deletion strains (involving genes HXK2, PYK1, REG1, PDE2 and PDC1). Some recombinant yeasts showed altered production of glycerol and pyruvate derived metabolites. REG1 and PDC1 deletion strains showed a strong reduction of acetic acid yield in aerobic fermentations. Since REG1 defective strains may be obtained by non-GMO approaches, these gene modifications show good promise to help reducing ethanol content in wines.

Photoinduced electron transfer involving eosin-tryptophan conjugates. Long-lived radical pair states for systems incorporating aromatic amino acid side chains

Energy Technology Data Exchange (ETDEWEB)

Jones, G. II; Farahat, C.W.; Oh, C. (Boston Univ., MA (United States))

1994-07-14

The electron-transfer photochemistry of the covalent derivatives of the dye eosin, in which the xanthene dye is covalently attached to the amino acid L-tryptophan via the thiohydantoin derivative, the tryptophan dipeptide, and an ethyl ester derivative, has been investigated. The singlet excited state of the dye is significantly quenched on attachment of the aromatic amino acid residue. Dye triplet states are also intercepted through intramolecular interaction of excited dye and amino acid pendants. Flash photolysis experiments verify that this interaction involves electron transfer from the indole side chains of tryptophan. Rate constants for electron transfer are discussed in terms of the distance relationships for the eosin chromophore and aromatic redox sites on peptide derivatives, the pathway for [sigma]-[pi] through-bond interaction between redox sites, and the multiplicity and state of protonation for electron-transfer intermediates. Selected electron-transfer photoreactions were studied under conditions of binding of the peptide derivatives in a high molecular weight, water-soluble, globular polymer, poly(vinyl-2-pyrrolidinone). 28 refs., 4 figs., 1 tab.

Comparative metabolomics profiling of engineered Saccharomyces cerevisiae lead to a strategy that improving β-carotene production by acetate supplementation.

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Xiao Bu

Full Text Available A comparative metabolomic analysis was conducted on recombinant Saccharomyces cerevisiae strain producing β-carotene and the parent strain cultivated with glucose as carbon source using gas chromatography-mass spectrometry (GC-MS, high performance liquid chromatography-mass spectrometry (HPLC-MS and ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS based approach. The results showed that most of the central intermediates associated with amino acids, carbohydrates, glycolysis and TCA cycle intermediates (acetic acid, glycerol, citric acid, pyruvic acid and succinic acid, fatty acids, ergosterol and energy metabolites were produced in a lower amount in recombinant strain, as compared to the parent strain. To increase β-carotene production in recombinant strain, a strategy that exogenous addition of acetate (10 g/l in exponential phase was developed, which could enhance most intracellular metabolites levels and result in 39.3% and 14.2% improvement of β-carotene concentration and production, respectively, which was accompanied by the enhancement of acetyl-CoA, fatty acids, ergosterol and ATP contents in cells. These results indicated that the amounts of intracellular metabolites in engineered strain are largely consumed by carotenoid formation. Therefore, maintaining intracellular metabolites pool at normal levels is essential for carotenoid biosynthesis. To relieve this limitation, rational supplementation of acetate could be a potential way because it can partially restore the levels of intracellular metabolites and improve the production of carotenoid compounds in recombinant S. cerevisiae.

Chiral bis(amino acid)- and bis(amino alcohol)-oxalamide gelators. Gelation properties, self-assembly motifs and chirality effects.

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Frkanec, Leo; Zinić, Mladen

2010-01-28

Bis(amino acid)- and bis(amino alcohol)oxalamide gelators represent the class of versatile gelators whose gelation ability is a consequence of strong and directional intermolecular hydrogen bonding provided by oxalamide units and lack of molecular symmetry due to the presence of two chiral centres. Bis(amino acid)oxalamides exhibit ambidextrous gelation properties, being capable to form gels with apolar and also highly polar solvent systems and tend to organise into bilayers or inverse bilayers in hydrogel or organic solvent gel assemblies, respectively. (1)H NMR and FTIR studies of gels revealed the importance of the equilibrium between the assembled network and smaller dissolved gelator assemblies. The organisation in gel assemblies deduced from spectroscopic structural studies are in certain cases closely related to organisations found in the crystal structures of selected gelators, confirming similar organisations in gel assemblies and in the solid state. The pure enantiomer/racemate gelation controversy is addressed and the evidence provided that rac-16 forms a stable toluene gel due to resolution into enantiomeric bilayers, which then interact giving gel fibres and a network of different morphology compared to its (S,S)-enantiomer gel. The TEM investigation of both gels confirmed distinctly different gel morphologies, which allowed the relationship between the stereochemical form of the gelator, the fibre and the network morphology and the network solvent immobilisation capacity to be proposed. Mixing of the constitutionally different bis(amino acid) and bis(amino alcohol)oxalamide gelators resulted in some cases in highly improved gelation efficiency denoted as synergic gelation effect (SGE), being highly dependent also on the stereochemistry of the component gelators. Examples of photo-induced gelation based on closely related bis(amino acid)-maleic acid amide and -fumaramide and stilbene derived oxalamides where gels form by irradiation of the solution of

Analysis of amino acid composition in proteins of animal tissues and foods as pre-column o-phthaldialdehyde derivatives by HPLC with fluorescence detection.

Science.gov (United States)

Dai, Zhaolai; Wu, Zhenlong; Jia, Sichao; Wu, Guoyao

2014-08-01

Studies of protein nutrition and biochemistry require reliable methods for analysis of amino acid (AA) composition in polypeptides of animal tissues and foods. Proteins are hydrolyzed by 6M HCl (110°C for 24h), 4.2M NaOH (105°C for 20 h), or proteases. Analytical techniques that require high-performance liquid chromatography (HPLC) include pre-column derivatization with 4-chloro-7-nitrobenzofurazan, 9-fluorenyl methylchloroformate, phenylisothiocyanate, naphthalene-2,3-dicarboxaldehyde, 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, and o-phthaldialdehyde (OPA). OPA reacts with primary AA (except cysteine or cystine) in the presence of 2-mercaptoethanol or 3-mercaptopropionic acid to form a highly fluorescent adduct. OPA also reacts with 4-amino-1-butanol and 4-aminobutane-1,3-diol produced from oxidation of proline and 4-hydroxyproline, respectively, in the presence of chloramine-T plus sodium borohydride at 60°C, or with S-carboxymethyl-cysteine formed from cysteine and iodoacetic acid at 25°C. Fluorescence of OPA derivatives is monitored at excitation and emission wavelengths of 340 and 455 nm, respectively. Detection limits are 50 fmol for AA. This technique offers the following advantages: simple procedures for preparation of samples, reagents, and mobile-phase solutions; rapid pre-column formation of OPA-AA derivatives and their efficient separation at room temperature (e.g., 20-25°C); high sensitivity of detection; easy automation on the HPLC apparatus; few interfering side reactions; a stable chromatography baseline for accurate integration of peak areas; and rapid regeneration of guard and analytical columns. Thus, the OPA method provides a useful tool to determine AA composition in proteins of animal tissues (e.g., skeletal muscle, liver, intestine, placenta, brain, and body homogenates) and foods (e.g., milk, corn grain, meat, and soybean meal). Copyright © 2014 Elsevier B.V. All rights reserved.

Recovery of acetic acid from waste streams by extractive distillation.

Science.gov (United States)

Demiral, H; Yildirim, M Ercengiz

2003-01-01

Wastes have been considered to be a serious worldwide environmental problem in recent years. Because of increasing pollution, these wastes should be treated. However, industrial wastes can contain a number of valuable organic components. Recovery of these components is important economically. Using conventional distillation techniques, the separation of acetic acid and water is both impractical and uneconomical, because it often requires large number of trays and a high reflux ratio. In practice special techniques are used depending on the concentration of acetic acid. Between 30 and 70% (w/w) acetic acid contents, extractive distillation was suggested. Extractive distillation is a multicomponent-rectification method similar in purpose to azeotropic distillation. In extractive distillation, to a binary mixture which is difficult or impossible to separate by ordinary means, a third component termed an entrainer is added which alters the relative volatility of the original constituents, thus permitting the separation. In our department acetic acid is used as a solvent during the obtaining of cobalt(III) acetate from cobalt(II) acetate by an electrochemical method. After the operation, the remaining waste contains acetic acid. In thiswork, acetic acid which has been found in this waste was recovered by extractive distillation. Adiponitrile and sulfolane were used as high boiling solvents and the effects of solvent feed rate/solution feed rate ratio and type were investigated. According to the experimental results, it was seem that the recovery of acetic acid from waste streams is possible by extractive distillation.

Disorder effects in Mn(12)-acetate at 83 K.

Science.gov (United States)

Cornia, Andrea; Fabretti, Antonio Costantino; Sessoli, Roberta; Sorace, Lorenzo; Gatteschi, Dante; Barra, Anne-Laure; Daiguebonne, Carole; Roisnel, Thierry

2002-07-01

The structure of hexadeca-mu-acetato-tetraaquadodeca-mu(3)-oxo-dodecamanganese bis(acetic acid) tetrahydrate, [Mn(12)O(12)(CH(3)COO)(16)(H(2)O)(4)] x 2CH(3)COOH x 4H(2)O, known as Mn(12)-acetate, has been determined at 83 (2) K by X-ray diffraction methods. The fourfold (S(4)) molecular symmetry is disrupted by a strong hydrogen-bonding interaction with the disordered acetic acid molecule of solvation, which displaces one of the acetate ligands in the cluster. Up to six Mn(12) isomers are potentially present in the crystal lattice, which differ in the number and arrangement of hydrogen-bonded acetic acid molecules. These results considerably improve the structural information available on this molecular nanomagnet, which was first synthesized and characterized by Lis [Acta Cryst. (1980), B36, 2042-2046].

Tub-Tag Labeling; Chemoenzymatic Incorporation of Unnatural Amino Acids.

Science.gov (United States)

Helma, Jonas; Leonhardt, Heinrich; Hackenberger, Christian P R; Schumacher, Dominik

2018-01-01

Tub-tag labeling is a chemoenzymatic method that enables the site-specific labeling of proteins. Here, the natural enzyme tubulin tyrosine ligase incorporates noncanonical tyrosine derivatives to the terminal carboxylic acid of proteins containing a 14-amino acid recognition sequence called Tub-tag. The tyrosine derivative carries a unique chemical reporter allowing for a subsequent bioorthogonal modification of proteins with a great variety of probes. Here, we describe the Tub-tag protein modification protocol in detail and explain its utilization to generate labeled proteins for advanced applications in cell biology, imaging, and diagnostics.

Plasma amino acids

Science.gov (United States)

Amino acids blood test ... types of methods used to determine the individual amino acid levels in the blood. ... test is done to measure the level of amino acids in the blood. An increased level of a ...

The effect of short-chain fatty acids on human monocyte-derived dendritic cells

DEFF Research Database (Denmark)

Nastasi, Claudia; Candela, Marco; Bonefeld, Charlotte Menné

2015-01-01

negligible effects, while both butyrate and propionate strongly modulated gene expression in both immature and mature human monocyte-derived DC. An Ingenuity pathway analysis based on the differentially expressed genes suggested that propionate and butyrate modulate leukocyte trafficking, as SCFA strongly......The gut microbiota is essential for human health and plays an important role in the pathogenesis of several diseases. Short-chain fatty acids (SCFA), such as acetate, butyrate and propionate, are end-products of microbial fermentation of macronutrients that distribute systemically via the blood....... The aim of this study was to investigate the transcriptional response of immature and LPS-matured human monocyte-derived DC to SCFA. Our data revealed distinct effects exerted by each individual SCFA on gene expression in human monocyte-derived DC, especially in the mature ones. Acetate only exerted...

Prolinimines: N-Amino-l-Pro-methyl Ester (Hydrazine) Schiff Bases from a Fish Gastrointestinal Tract-Derived Fungus, Trichoderma sp. CMB-F563.

Science.gov (United States)

Mohamed, Osama G; Khalil, Zeinab G; Capon, Robert J

2018-01-19

A rice cultivation of a fish gastrointestinal tract-derived fungus, Trichoderma sp. CMB-F563, yielded natural products incorporating a rare hydrazine moiety, embedded within a Schiff base. Structures inclusive of absolute configurations were assigned to prolinimines A-D (1-4) on the basis of detailed spectroscopic and C 3 Marfey's analysis, as well as biosynthetic considerations, biomimetic total synthesis, and chemical transformations. Of note, monomeric 1 proved to be acid labile and, during isolation, underwent quantitative transformation to dimeric 3 and trimeric 4. Prolinimines are only the second reported natural products incorporating an N-amino-Pro residue, the first to include l-Pro, the first to occur as Schiff bases, and the first to be isolated from a microorganism.

Synthesis and characterization of new polyamides derived from alanine and valine derivatives

Directory of Open Access Journals (Sweden)

El-Faham Ayman

2012-11-01

Full Text Available Abstract Background Many efforts have been recently devoted to design, investigate and synthesize biocompatible, biodegradable polymers for applications in medicine for either the fabrication of biodegradable devices or as drug delivery systems. Many of them consist of condensation of polymers having incorporated peptide linkages susceptible to enzymatic cleavage. Polyamides (PAs containing α-amino acid residues such as L-leucine, L-alanine and L-phenylalanine have been reported as biodegradable materials. Furthermore, polyamides (PAs derived from C10 and C14 dicarboxylic acids and amide-diamines derived from 1,6-hexanediamine or 1,12-dodecanediamine and L-phenylalanine, L-valyl-L-phenylalanine or L-phenylalanyl-L-valine residues have been reported as biocompatible polymers. We have previously described the synthesis and thermal properties of a new type of polyamides-containing amino acids based on eight new symmetric meta-oriented protected diamines derived from coupling of amino acids namely; Fomc-glycine, Fmoc-alanine, Fomc-valine and Fomc-leucine with m-phenylene diamine or 2,6-diaminopyridine. Results revealed that incorporation of pyridine onto the polymeric backbone of all series decreases the thermal stability. Here we describe another family of polyamides based on benzene dicarboxylic acid, pyridine dicarboxylic acid, and α-amino acid linked to benzidine and 4,4′-oxydianiline to study the effect of the dicarboxylic acid as well as the amino acids on the nature and thermal stability of the polymers. Results We report here the preparation of a new type of polyamides based on benzene dicarboxylic acid, pyridine dicarboxylic acid, and α-amino acid linked to benzidine and 4,4′-oxydianiline to study the effect of the dicarboxylic acid as well as the amino acids on the nature and thermal stability of polymers. The thermal properties of the polymers were evaluated by different techniques. Results revealed that structure-thermal property

Effects of dietary substitution of mixed amino acids for glucose on the splanchnic metabolism of plasma triglycerides, cholesterol, carbohydrates, and amino acids in conscious fed baboons.

Science.gov (United States)

Wolfe, B M; Redinger, R N; Marliss, E B; Grace, D M

1983-04-01

Splanchnic metabolism was studied in the fed state during prolonged constant intravenous administration of tracer amounts of [9,10]-3H palmitic acid and the calculated isocaloric intraduodenal administration (13 mg/min X kg body wt0.75) of either (1) glucose, (2) 15% mixed amino acids and 85% glucose or (3) 45% mixed amino acids and 55% glucose to conscious, restrained female baboons that had been maintained on a similar diet (supplemented in essential nutrients) for the previous 9 days. Secretion of plasma triglycerides from the splanchnic region was quantified from splanchnic flow and radiochemical measurements of transsplanchnic gradients of 3H-labeled free fatty acids and triglycerides. Mean splanchnic secretion of plasma triglycerides increased significantly as the proportion of dietary calories derived from amino acids was varied from 0 to 15 to 45% (mean values 1.1 +/- 0.1, 2.6 +/- 0.2 and 4.2 +/- 0.3 mumol/min kg body wt0.75, respectively, p less than 0.05). Increased triglyceride secretion was attributable to both significantly higher rates of esterification of free fatty acids taken up in the splanchnic region to triglycerides released into hepatic venous blood plasma (mean values 10 +/- 1, 16 +/- 2 and 34 +/- 5%, respectively) and to significantly higher rates of secretion of triglycerides derived from precursors other than free fatty acids. Higher intake of amino acids was also associated with both higher plasma concentrations of cholesterol and higher values for hepatic oxidation of cholesterol to bile acids.(ABSTRACT TRUNCATED AT 250 WORDS)

An integrated scheme for the simultaneous determination of biogenic amines, precursor amino acids, and related metabolites by liquid chromatography with electrochemical detection.

Science.gov (United States)

Oka, K; Kojima, K; Togari, A; Nagatsu, T; Kiss, B

1984-06-08

A new method using high-performance liquid chromatography with electrochemical detection (HPLC-ED) for the simultaneous determination of monoamines, their precursor amino acids, and related major metabolites in small samples of brain tissue weighing from 0.5 to 50 mg is described. The method is based on the preliminary isolation of monoamines (dopamine, norepinephrine, epinephrine, and serotonin), their precursor amino acids (tyrosine, 3,4-dihydroxyphenylalanine, tryptophan and 5-hydroxytryptophan), and their major metabolites (3-methoxytyramine, normetanephrine, 3,4-dihydroxyphenylacetic acid, homovanillic acid, vanillylmandelic acid, 3-methoxy-4-hydroxyphenylethyleneglycol, and 5-hydroxyindoleacetic acid) by chromatography on small columns of Amberlite CG-50 and Dowex 50W, and by ethyl acetate extraction. All the compounds in the four isolated fractions were measured by HPLC-ED on a reversed-phase column under four different conditions. The sensitivity was from 0.1 to 40 pmol, depending on the substances analysed. This newly established method was applied to the study of the effects of an aromatic L-amino acid decarboxylase inhibitor (NSD-1015) and a monoamine oxidase inhibitor (pargyline) on the levels of monoamines, their precursor amino acids and their major metabolites in brain regions of mice.

Automated GC-MS analysis of free amino acids in biological fluids.

Science.gov (United States)

Kaspar, Hannelore; Dettmer, Katja; Gronwald, Wolfram; Oefner, Peter J

2008-07-15

A gas chromatography-mass spectrometry (GC-MS) method was developed for the quantitative analysis of free amino acids as their propyl chloroformate derivatives in biological fluids. Derivatization with propyl chloroformate is carried out directly in the biological samples without prior protein precipitation or solid-phase extraction of the amino acids, thereby allowing automation of the entire procedure, including addition of reagents, extraction and injection into the GC-MS. The total analysis time was 30 min and 30 amino acids could be reliably quantified using 19 stable isotope-labeled amino acids as internal standards. Limits of detection (LOD) and lower limits of quantification (LLOQ) were in the range of 0.03-12 microM and 0.3-30 microM, respectively. The method was validated using a certified amino acid standard and reference plasma, and its applicability to different biological fluids was shown. Intra-day precision for the analysis of human urine, blood plasma, and cell culture medium was 2.0-8.8%, 0.9-8.3%, and 2.0-14.3%, respectively, while the inter-day precision for human urine was 1.5-14.1%.

Density, refraction index and vapor–liquid equilibria of N-methyl-2-hydroxyethylammonium butyrate plus (methyl acetate or ethyl acetate or propyl acetate) at several temperatures

International Nuclear Information System (INIS)

Alvarez, V.H.; Mattedi, S.; Aznar, M.

2013-01-01

Highlights: ► Densities, refraction indices and VLE were measured for ester + m-2-HEAB mixtures. ► V E , apparent molar volumes and thermal expansion coefficients were calculated. ► Peng–Robinson EoS + Wong–Sandler mixing rule + COSMO-SAC predicted the data. -- Abstract: This paper reports the densities, refraction indices, and vapor liquid equilibria for binary systems ester + N-methyl-2-hydroxyethylammonium butyrate (m-2-HEAB): methyl acetate (1) + m-2-HEAB (2), ethyl acetate (1) + m-2-HEAB and propyl acetate (1) + m-2-HEAB (2). The excess molar volumes, deviations in the refraction index, apparent molar volumes, and thermal expansion coefficients for the binary systems were fitted to polynomial equations. The Peng–Robinson equation of state, coupled with the Wong–Sandler mixing rule, is used to describe the experimental data. Since the predictive activity coefficient model COSMO-SAC is used in the Wong–Sandler mixing rule, the resulting thermodynamic model is a completely predictive one. The prediction results for the density and for the vapor–liquid equilibria have a deviation lower than 1.0% and 1.1%, respectively

21 CFR 862.1390 - 5-Hydroxyindole acetic acid/serotonin test system.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 8 2010-04-01 2010-04-01 false 5-Hydroxyindole acetic acid/serotonin test system... Test Systems § 862.1390 5-Hydroxyindole acetic acid/serotonin test system. (a) Identification. A 5-hydroxyindole acetic acid/serotonin test system is a device intended to measure 5-hydroxyindole acetic acid...

Synthesis and dyeing properties of some new monoazo disperse dyes derived from 2-amino-4-(2′,4′-dichlorophenyl-1,3 thiazole

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Divyesh R. Patel

2014-12-01

Full Text Available Ten new monoazo disperse dyes (4a–j have been synthesized by coupling of diazotized 2-amino-4-(2′,4′-dichlorophenyl-1,3 thiazole (2 with various N-alkyl derivatives of substituted aniline (3a–j and their dyeing performance on polyester fiber has been assessed. These dyes are characterized by elemental analysis, UV–vis spectra, IR and NMR spectroscopy. The absorption maxima (λmax were recorded in DMF and were found to be in the range of 530–600 nm. The dyed polyester fabric showed fair to very good light fastness and very good to excellent washing and rubbing fastness properties with superior depth and levelness.

[Determination of residual solvents in 7-amino-3-chloro cephalosporanic acid by gas chromatography].

Science.gov (United States)

Ma, Li; Yao, Tong-wei

2011-01-01

To develop a gas chromatography method for determination of residual solvents in 7-amino-3-chloro cephalosporanic acid (7-ACCA). The residual levels of acetone, methanol, dichloromethane, ethyl acetate, isobutanol, pyridine and toluene in 7-ACCA were measured by gas chromatography using Agilent INNOWAX capillary column (30 m × 0.32 mm,0.5 μm). The initial column temperature was 70° maintained for 6 min and then raised (10°C/min) to 160°C for 1 min. Nitrogen gas was used as carrier and FID as detector. The flow of carrier was 1.0 ml/min, the temperature of injection port and detector was 200°C and 250°C, respectively. The limits of detection for acetone, methanol, dichloromethane, ethyl acetate, isobutanol, pyridine, toluene in 7-ACCA were 2.5 μg/ml, 1.5 μg/ml, 15 μg/ml, 2.5 μg/ml, 2.5 μg/ml, 2.5 μg/ml and 11 μg/ml, respectively. Only acetone was detected in the sample, and was less than the limits of Ch.P. The method can effectively detect the residual solvents in 7-ACCA.

preparation and nucleophilic substitution of the 2,4,6

African Journals Online (AJOL)

Mgina

Three methods for preparation of D-amino acids by nucleophilic substitution on derivatives of ... bioactivity of the peptide (Wenger 1985, ... Acetic acid (0.29 mL, 5 mmol) was added, and the mixture was further stirred for 5 h at rt under ... methanol/dichloromethane) to yield a white ... temperature, diluted with water, extracted.

Amino acid catabolism-directed biofuel production in Clostridium sticklandii: An insight into model-driven systems engineering

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C Sangavai

2017-12-01

Full Text Available Model-driven systems engineering has been more fascinating process for the microbial production of biofuel and bio-refineries in chemical and pharmaceutical industries. Genome-scale modeling and simulations have been guided for metabolic engineering of Clostridium species for the production of organic solvents and organic acids. Among them, Clostridium sticklandii is one of the potential organisms to be exploited as a microbial cell factory for biofuel production. It is a hyper-ammonia producing bacterium and is able to catabolize amino acids as important carbon and energy sources via Stickland reactions and the development of the specific pathways. Current genomic and metabolic aspects of this bacterium are comprehensively reviewed herein, which provided information for learning about protein catabolism-directed biofuel production. It has a metabolic potential to drive energy and direct solventogenesis as well as acidogenesis from protein catabolism. It produces by-products such as ethanol, acetate, n-butanol, n-butyrate and hydrogen from amino acid catabolism. Model-driven systems engineering of this organism would improve the performance of the industrial sectors and enhance the industrial economy by using protein-based waste in environment-friendly ways. Keywords: Biofuel, Amino acid catabolism, Genome-scale model, Metabolic engineering, Systems biology, ABE fermentation, Clostridium sticklandii

Structure, Content, and Bioactivity of Food-Derived Peptides in the Body.

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Sato, Kenji

2018-03-28

Orally administered peptides are assumed to be degraded into amino acids in the body. However, our recent studies revealed some food-derived prolyl and pyroglutamyl peptides with 2-3 amino acid residues in the blood of humans and animals, while most of the peptides in the endoproteinase digest of food protein are degraded by exopeptidase. Some food-derived dipeptides in the body display in vitro and in vivo biological activities. These facts indicate that the biological activities of food-derived peptides in the body rather than those in food are crucial to understanding the mechanism of the beneficial effects of orally administered peptides.

Synthesis and characterization of ester and amide derivatives of titanium(IV) carboxymethylphosphonate

International Nuclear Information System (INIS)

Melánová, Klára; Beneš, Ludvík; Trchová, Miroslava; Svoboda, Jan; Zima, Vítězslav

2013-01-01

A set of layered ester and amide derivatives of titanium(IV) carboxymethylphosphonate was prepared by solvothermal treatment of amorphous titanium(IV) carboxymethylphosphonate with corresponding 1-alkanols, 1,ω-alkanediols, 1-aminoalkanes, 1,ω-diaminoalkanes and 1,ω-amino alcohols and characterized by powder X-ray diffraction, IR spectroscopy and thermogravimetric analysis. Whereas alkyl chains with one functional group form bilayers tilted to the layers, 1,ω-diaminoalkanes and most of 1,ω-alkanediols form bridges connecting the adjacent layers. In the case of amino alcohols, the alkyl chains form bilayer and either hydroxyl or amino group is used for bonding. This simple method for the synthesis of ester and amide derivatives does not require preparation of acid chloride derivative as a precursor or pre-intercalation with alkylamines and can be used also for the preparation of ester and amide derivatives of titanium carboxyethylphosphonate and zirconium carboxymethylphosphonate. - Graphical abstract: Ester and amide derivatives of layered titanium carboxymethylphosphonate were prepared by solvothermal treatment of amorphous solid with alkanol or alkylamine. - Highlights: • Ester and amide derivatives of titanium carboxymethylphosphonate. • Solvothermal treatment of amorphous solid with alkanol or alkylamine. • Ester and amide formation confirmed by IR spectroscopy

Metabolic Characterization of Acutely Isolated Hippocampal and Cerebral Cortical Slices Using [U-13C]Glucose and [1,2-13C]Acetate as Substrates.

Science.gov (United States)

McNair, Laura F; Kornfelt, Rasmus; Walls, Anne B; Andersen, Jens V; Aldana, Blanca I; Nissen, Jakob D; Schousboe, Arne; Waagepetersen, Helle S

2017-03-01

Brain slice preparations from rats, mice and guinea pigs have served as important tools for studies of neurotransmission and metabolism. While hippocampal slices routinely have been used for electrophysiology studies, metabolic processes have mostly been studied in cerebral cortical slices. Few comparative characterization studies exist for acute hippocampal and cerebral cortical slices, hence, the aim of the current study was to characterize and compare glucose and acetate metabolism in these slice preparations in a newly established incubation design. Cerebral cortical and hippocampal slices prepared from 16 to 18-week-old mice were incubated for 15-90 min with unlabeled glucose in combination with [U- 13 C]glucose or [1,2- 13 C]acetate. Our newly developed incubation apparatus allows accurate control of temperature and is designed to avoid evaporation of the incubation medium. Subsequent to incubation, slices were extracted and extracts analyzed for 13 C-labeling (%) and total amino acid contents (µmol/mg protein) using gas chromatography-mass spectrometry and high performance liquid chromatography, respectively. Release of lactate from the slices was quantified by analysis of the incubation media. Based on the measured 13 C-labeling (%), total amino acid contents and relative activity of metabolic enzymes/pathways, we conclude that the slice preparations in the current incubation apparatus exhibited a high degree of metabolic integrity. Comparison of 13 C-labeling observed with [U- 13 C]glucose in slices from cerebral cortex and hippocampus revealed no significant regional differences regarding glycolytic or total TCA cycle activities. On the contrary, results from the incubations with [1,2- 13 C]acetate suggest a higher capacity of the astrocytic TCA cycle in hippocampus compared to cerebral cortex. Finally, we propose a new approach for assessing compartmentation of metabolite pools between astrocytes and neurons using 13 C-labeling (%) data obtained from

Enhancing acetone biosynthesis and acetone-butanol-ethanol fermentation performance by co-culturing Clostridium acetobutylicum/Saccharomyces cerevisiae integrated with exogenous acetate addition.

Science.gov (United States)

Luo, Hongzhen; Ge, Laibing; Zhang, Jingshu; Ding, Jian; Chen, Rui; Shi, Zhongping

2016-01-01

Acetone is the major by-product in ABE fermentations, most researches focused on increasing butanol/acetone ratio by decreasing acetone biosynthesis. However, economics of ABE fermentation industry strongly relies on evaluating acetone as a valuable platform chemical. Therefore, a novel ABE fermentation strategy focusing on bio-acetone production by co-culturing Clostridium acetobutylicum/Saccharomyces cerevisiae with exogenous acetate addition was proposed. Experimental and theoretical analysis revealed the strategy could, enhance C. acetobutylicum survival oriented amino acids assimilation in the cells; control NADH regeneration rate at moderately lower level to enhance acetone synthesis but without sacrificing butanol production; enhance the utilization ability of C. acetobutylicum on glucose and direct most of extra consumed glucose into acetone/butanol synthesis routes. By implementing the strategy using synthetic or acetate fermentative supernatant, acetone concentrations increased to 8.27-8.55g/L from 5.86g/L of the control, while butanol concentrations also elevated to the higher levels of 13.91-14.23g/L from 11.63g/L simultaneously. Copyright © 2015 Elsevier Ltd. All rights reserved.

Conductive iron oxides accelerate thermophilic methanogenesis from acetate and propionate.

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Yamada, Chihaya; Kato, Souichiro; Ueno, Yoshiyuki; Ishii, Masaharu; Igarashi, Yasuo

2015-06-01

Anaerobic digester is one of the attractive technologies for treatment of organic wastes and wastewater, while continuous development and improvements on their stable operation with efficient organic removal are required. Particles of conductive iron oxides (e.g., magnetite) are known to facilitate microbial interspecies electron transfer (termed as electric syntrophy). Electric syntrophy has been reported to enhance methanogenic degradation of organic acids by mesophilic communities in soil and anaerobic digester. Here we investigated the effects of supplementation of conductive iron oxides (magnetite) on thermophilic methanogenic microbial communities derived from a thermophilic anaerobic digester. Supplementation of magnetite accelerated methanogenesis from acetate and propionate under thermophilic conditions, while supplementation of ferrihydrite also accelerated methanogenesis from propionate. Microbial community analysis revealed that supplementation of magnetite drastically changed bacterial populations in the methanogenic acetate-degrading cultures, in which Tepidoanaerobacter sp. and Coprothermobacter sp. dominated. These results suggest that supplementation of magnetite induce electric syntrophy between organic acid-oxidizing bacteria and methanogenic archaea and accelerate methanogenesis even under thermophilic conditions. Findings from this study would provide a possibility for the achievement of stably operating thermophilic anaerobic digestion systems with high efficiency for removal of organics and generation of CH4. Copyright © 2014 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

Amino acids

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... this page: //medlineplus.gov/ency/article/002222.htm Amino acids To use the sharing features on this page, please enable JavaScript. Amino acids are organic compounds that combine to form proteins . ...

Acetate adaptation of clostridia tyrobutyricum for improved fermentation production of butyrate.

Science.gov (United States)

Jaros, Adam M; Rova, Ulrika; Berglund, Kris A

2013-12-01

Clostridium tyrobutyricum ATCC 25755 is an acidogenic bacterium capable of utilizing xylose for the fermentation production of butyrate. Hot water extraction of hardwood lingocellulose is an efficient method of producing xylose where autohydrolysis of xylan is catalysed by acetate originating from acetyl groups present in hemicellulose. The presence of acetic acid in the hydrolysate might have a severe impact on the subsequent fermentations. In this study the fermentation kinetics of C. tyrobutyricum cultures after being classically adapted for growth at 26.3 g/L acetate equivalents were studied. Analysis of xylose batch fermentations found that even in the presence of high levels of acetate, acetate adapted strains had similar fermentation kinetics as the parental strain cultivated without acetate. The parental strain exposed to acetate at inhibitory conditions demonstrated a pronounced lag phase (over 100 hours) in growth and butyrate production as compared to the adapted strain (25 hour lag) or non-inhibited controls (0 lag). Additional insight into the metabolic pathway of xylose consumption was gained by determining the specific activity of the acetate kinase (AK) enzyme in adapted versus control batches. AK activity was reduced by 63% in the presence of inhibitory levels of acetate, whether or not the culture had been adapted.

Theoretical predictions of anti-corrosive properties of THAM and its derivatives.

Science.gov (United States)

Malinowski, Szymon; Jaroszyńska-Wolińska, Justyna; Herbert, Tony

2017-12-04

We present quantum chemical theoretical estimations of the anti-corrosive properties of THAM (tris(hydroxymethyl)aminomethane) and three derivatives that differ in the number of benzene rings: THAM-1 (2-amino-3-hydroxy-2-(hydroxymethyl) propylobenzoate), THAM-2 (2-amino-2-(hydroxymetyl)prapan-1,3-diyldibenzoate) and THAM-3 (2-amino-propan-1,2,3-triyltribenzoate). Fourteen exchange-correlation functionals based on the density functional theory (DFT) were chosen for quantum chemical study of THAM derivatives. The objective was to examine the effect of benzene rings on potential anti-corrosive properties of THAM compounds. The results indicate that the addition of benzene rings in THAM derivatives is likely to significantly enhance electrostatic bonding of a THAM-based coating to a presented metal surface and, thus, its adhesion and long-term effect in corrosion inhibition. Whereas it is clear that all three derivatives appear to be superior in their bonding characteristics to pure THAM, the potential order of merit between the three is less clear, although THAM-3 presents as possibly superior.

Radiolabeled derivatives of folic acid

International Nuclear Information System (INIS)

1980-01-01

Derivatives of folic acid are described, in which the α-carboxyl group is substituted with an amino compound having an aromatic or heterocyclic ring substituent which is capable of being radiolabelled. Particularly mentioned as a radiolabel is 125 I. (author)

Hydrogen isotope analysis of amino acids and whole cells reflects biosynthetic processing of nutrient- and water-derived hydrogen

Science.gov (United States)

Griffin, P.; Newsome, S.; Steele, A.; Fogel, M. L.

2011-12-01

Hydrogen (H) isotopes serve as sensitive tracers of biochemical processes that can be exploited to answer critical questions in biogeochemistry, ecology, and microbiology. Despite this apparent utility, relatively little is known about the specific mechanisms of H isotope fractionation involved in biosynthesis. In order to understand how organisms incorporate hydrogen from their chemical milieu into biomass, we have cultured the model bacterium E. coli MG1655 in a variety of media composed of deuterium-labeled nutrients and waters. Isotopic analysis of bulk cell mass reveals that the H fractionation between media water and cell material varies as a function of the nutrient source, with commonly used organic food sources (glucose and tryptone) leading to far smaller fractionation signals than non-standard ones (such as formamide, adenine, and urea). In addition, we have completed compound specific isotope analysis of amino acids using combined GC-IRMS. Amino acids harvested from E. coli cultured on glucose in water of varied D/H composition posses an extraordinary range of isotopic compositions (400-600 %). Furthermore, these amino acids follow a systematic distribution of D/H where proline is always heaviest and glycine is always lightest. However, when the short-chain peptide tryptone is used in place of glucose, only the non-essential amino acids reflect media water D/H values, suggesting the direct incorporation of some media-borne amino acids into cellular protein. These observations provide a foundation for understanding the cellular routing of hydrogen obtained from food and water sources and indicate that D/H analysis can serve as a powerful probe of biological function.

A simple spectrophotometric method for the determination of arsenic in industrial and environmental samples using 2,4-Dihydroxy benzophenone-2-amino thiophenol.

Science.gov (United States)

Deepa, K; Lingappa, Y

2014-04-24

2,4-Dihydroxy benzophenone-2-amino thiophenol (BPBT) has been proposed as new analytical reagent for the direct non-extractive spectrophotometric determination of arsenic. The reagent reacts with arsenic in acidic medium (pH=6.0, sodium acetate-acetic acid buffer) to form light greenish yellow colored 1:1 (M:L) complex. Maximum absorbance was obtained at 343 nm and remains constant for over 24 h. The molar absorptivity and Sandell's sensitivity of BPBT are found to be 6.01×10(4) L mol(-1)cm(-1) and 0.0016 μg cm(-2) respectively. The system obeys Beer's law in the range of 0.125-2.637 μg/ml of As (III). Since BPBT method is more sensitive, it was applied for the determination of arsenic in some environmental water samples. Copyright © 2013 Elsevier B.V. All rights reserved.

The behaviour of tungsten electrodes in a mixture of acetic acid and acetic anhydride

International Nuclear Information System (INIS)

Pastor, T.J.; Vajgand, V.H.

1976-01-01

Tungsten electrodes have advantageously been used for potentiometric end-point detection in perchloric acid titration of bases in a mixture of acetic acid and acetic anhydride. They have also given good results in biamperometric detection of the equivalence point in continuous coulometric titration of small quantities of bases and acids in the same solvent. Tungsten electrodes in the presence of quinhydrone behave like platinum electrodes, but in biamperometric end-point determination in the absence of quinhydrone it is better to remove the oxide layer from their surface. Some other factors affecting their behaviour have also been studied. Errors in determination do not exceed +-2% even in titration of very small quantities of substances. (author)

Mass Spectrometric Characteristics of Prenylated Indole Derivatives from Marine-Derived Penicillium sp. NH-SL.

Science.gov (United States)

Ding, Hui; Ding, Wanjing; Ma, Zhongjun

2017-03-22

Two prenylated indole alkaloids were isolated from the ethyl acetate extracts of a marine-derived fungus Penicillium sp. NH-SL and one of them exhibited potent cytotoxic activity against mouse hepa 1c1c7 cells. In order to detect other bioactive analogs, we used liquid chromatogram tandem mass spectrometry (LC-MS/MS) to analyze the mass spectrometric characteristics of the isolated compounds as well as the crude extracts. As a result, three other analogs were detected, and their structures were deduced according to the similar fragmentation patterns. This is the first systematic report on the mass spectrometric characteristics of prenylated indole derivatives.

Radiation sterilization of hydrocortisone acetate

International Nuclear Information System (INIS)

Charef, A.; Boussaha, A.

1989-09-01

The feasibility of using high energy ionizing radiation for the sterilization of hydrocortisone acetate was investigated. Hydrocortisone acetate in the form of powder was exposed to different dose levels of gamma radiation using a Cobalt-60 source. The irradiated samples were examined by various physico-chemical techniques in order to detect possible radiolysis products. It was of interest to know if one could insure sterility and retain biological properties of the drug by suitable choice of radiation dose. The results showed that a 10 KGy radiation dose causes no change in the physico-chemical properties of the drug and is sufficient to obtain contaminant-free product

Understanding the hydrolysis mechanism of ethyl acetate catalyzed by an aqueous molybdocene: a computational chemistry investigation.

Science.gov (United States)

Tílvez, Elkin; Cárdenas-Jirón, Gloria I; Menéndez, María I; López, Ramón

2015-02-16

A thoroughly mechanistic investigation on the [Cp2Mo(OH)(OH2)](+)-catalyzed hydrolysis of ethyl acetate has been performed using density functional theory methodology together with continuum and discrete-continuum solvation models. The use of explicit water molecules in the PCM-B3LYP/aug-cc-pVTZ (aug-cc-pVTZ-PP for Mo)//PCM-B3LYP/aug-cc-pVDZ (aug-cc-pVDZ-PP for Mo) computations is crucial to show that the intramolecular hydroxo ligand attack is the preferred mechanism in agreement with experimental suggestions. Besides, the most stable intermediate located along this mechanism is analogous to that experimentally reported for the norbornenyl acetate hydrolysis catalyzed by molybdocenes. The three most relevant steps are the formation and cleavage of the tetrahedral intermediate immediately formed after the hydroxo ligand attack and the acetic acid formation, with the second one being the rate-determining step with a Gibbs energy barrier of 36.7 kcal/mol. Among several functionals checked, B3LYP-D3 and M06 give the best agreement with experiment as the rate-determining Gibbs energy barrier obtained only differs 0.2 and 0.7 kcal/mol, respectively, from that derived from the experimental kinetic constant measured at 296.15 K. In both cases, the acetic acid elimination becomes now the rate-determining step of the overall process as it is 0.4 kcal/mol less stable than the tetrahedral intermediate cleavage. Apart from clarifying the identity of the cyclic intermediate and discarding the tetrahedral intermediate formation as the rate-determining step for the mechanism of the acetyl acetate hydrolysis catalyzed by molybdocenes, the small difference in the Gibbs energy barrier found between the acetic acid formation and the tetrahedral intermediate cleavage also uncovers that the rate-determining step could change when studying the reactivity of carboxylic esters other than ethyl acetate substrate specific toward molybdocenes or other transition metal complexes. Therefore

Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

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Mario J. Simirgiotis

2014-11-01

Full Text Available An enantioselective total synthesis of the natural amino acid (2S,4R,5R-4,5-di-hydroxy-pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The structures of the compounds synthesized were elucidated on the basis of comprehensive spectroscopic (NMR and MS and computational analysis.

Isotopic evidence for extraterrestrial non- racemic amino acids in the Murchison meteorite

Science.gov (United States)

Engel, M. H.; Macko, S. A.

1997-09-01

Many amino acids contain an asymmetric centre, occurring as laevorotatory, L, or dextrorotatory, D, compounds. It is generally assumed that abiotic synthesis of amino acids on the early Earth resulted in racemic mixtures (L- and D-enantiomers in equal abundance). But the origin of life required, owing to conformational constraints, the almost exclusive selection of either L- or D-enantiomers, and the question of why living systems on the Earth consist of L-enantiomers rather than D-enantiomers is unresolved. A substantial fraction of the organic compounds on the early Earth may have been derived from comet and meteorite impacts. It has been reported previously that amino acids in the Murchison meteorite exhibit an excess of L-enantiomers, raising the possibility that a similar excess was present in the initial inventory of organic compounds on the Earth. The stable carbon isotope compositions of individual amino acids in Murchison support an extraterrestrial origin-rather than a terrestrial overprint of biological amino acids-although reservations have persisted (see, for example, ref. 9). Here we show that individual amino-acid enantiomers from Murchison are enriched in 15N relative to their terrestrial counterparts, so confirming an extraterrestrial source for an L-enantiomer excess in the Solar System that may predate the origin of life on the Earth.

The Genealogical Tree of Ethanol: Gas-phase Formation of Glycolaldehyde, Acetic Acid, and Formic Acid

Science.gov (United States)

Skouteris, Dimitrios; Balucani, Nadia; Ceccarelli, Cecilia; Vazart, Fanny; Puzzarini, Cristina; Barone, Vincenzo; Codella, Claudio; Lefloch, Bertrand

2018-02-01

Despite the harsh conditions of the interstellar medium, chemistry thrives in it, especially in star-forming regions where several interstellar complex organic molecules (iCOMs) have been detected. Yet, how these species are synthesized is a mystery. The majority of current models claim that this happens on interstellar grain surfaces. Nevertheless, evidence is mounting that neutral gas-phase chemistry plays an important role. In this paper, we propose a new scheme for the gas-phase synthesis of glycolaldehyde, a species with a prebiotic potential and for which no gas-phase formation route was previously known. In the proposed scheme, the ancestor is ethanol and the glycolaldehyde sister species are acetic acid (another iCOM with unknown gas-phase formation routes) and formic acid. For the reactions of the new scheme with no available data, we have performed electronic structure and kinetics calculations deriving rate coefficients and branching ratios. Furthermore, after a careful review of the chemistry literature, we revised the available chemical networks, adding and correcting several reactions related to glycolaldehyde, acetic acid, and formic acid. The new chemical network has been used in an astrochemical model to predict the abundance of glycolaldehyde, acetic acid, and formic acid. The predicted abundance of glycolaldehyde depends on the ethanol abundance in the gas phase and is in excellent agreement with the measured one in hot corinos and shock sites. Our new model overpredicts the abundance of acetic acid and formic acid by about a factor of 10, which might imply a yet incomplete reaction network.

Tetrazine-Containing Amino Acid for Peptide Modification and Live Cell Labeling.

Directory of Open Access Journals (Sweden)

Zhongqiu Ni

Full Text Available A novel amino acid derivative 3-(4-(1, 2, 4, 5-tetrazine-3-yl phenyl-2-aminopropanoic acid was synthesized in this study. The compound possessed better water-solubility and was synthesized more easily compared with the well-known and commercially available 3-(p-benzylamino-1, 2, 4, 5-tetrazine. Tetrazine-containing amino acid showed excellent stability in biological media and might be used for cancer cell labeling. Moreover, the compound remained relatively stable in 50% TFA/DCM with little decomposition after prolonged exposure at room temperature. The compound could be utilized as phenylalanine or tyrosine analogue in peptide modification, and the tetrazine-containing peptide demonstrated more significant biological activity than that of the parent peptide. The combination of tetrazine group and amino acid offered broad development prospects of the bioorthogonal labeling and peptide synthesis.

Syn-Selective Synthesis of β-Branched α-Amino Acids by Alkylation of Glycine-Derived Imines with Secondary Sulfonates.

Science.gov (United States)

Lou, Sha; McKenna, Grace M; Tymonko, Steven A; Ramirez, Antonio; Benkovics, Tamas; Conlon, David A; González-Bobes, Francisco

2015-10-16

A syn-selective synthesis of β-branched α-amino acids has been developed based on the alkylation of glycine imine esters with secondary sulfonates. The potassium counterion for the enolate, the solvent, and the leaving group on the electrophile were key levers to maximize the diasteroselectivity of the alkylation. The optimized conditions enabled a straightforward preparation of a number of β-branched α-amino acids that can be challenging to obtain.

Effect of sodium acetate on the volumetric behaviour of some mono-, di-, and tri-saccharides in aqueous solutions over temperature range (288.15 to 318.15) K

Energy Technology Data Exchange (ETDEWEB)

Banipal, Parampaul K., E-mail: pkbanipal@yahoo.co [Department of Chemistry, Guru Nanak Dev University, Amritsar 143 005 (India); Singh, Vickramjeet [Department of Chemistry, Guru Nanak Dev University, Amritsar 143 005 (India); Banipal, Tarlok S. [Department of Applied Chemistry, Guru Nanak Dev University, Amritsar 143 005 (India)

2010-01-15

The standard partial molar volumes, V{sub 2}{sup 0} at infinite dilution of eight monosaccharides [D(+)-xylose, D(-)-arabinose, D(-)-ribose, L(-)-sorbose, D(-)-fructose, D(+)-galactose, D(+)-glucose, and D(+)-mannose], six disaccharides [D(+)-cellobiose, sucrose, D(+)-melibiose, D(+)-lactose monohydrate, D(+)-trehalose dihydrate, and D(+)-maltose monohydrate] and two trisaccharides [D(+)-melizitose and D(+)-raffinose pentahydrate] (molalities of saccharides range from (0.03 to 0.12) mol . kg{sup -1}) have been determined in water and in (0.5, 1.0, 2.0, and 3.0) mol . kg{sup -1} aqueous sodium acetate solutions at temperatures, T = (288.15, 298.15, 308.15, and 318.15) K from density measurements using a vibrating-tube digital densimeter. From these results, corresponding standard partial molar volumes of transfer, DELTA{sub t}V{sub 2}{sup 0} have been determined for the transfer of various saccharides from water to aqueous solutions of sodium acetate. Positive values of DELTA{sub t}V{sub 2}{sup 0} were obtained for most of the saccharides, whose magnitude increase with the concentration of sodium acetate as well as temperature. However, negative DELTA{sub t}V{sub 2}{sup 0} values were observed for L(-)-sorbose, D(-)-fructose and D(+)-xylose at lower concentrations of co-solute. The negative magnitude of DELTA{sub t}V{sub 2}{sup 0} values decrease with rise of temperature from (288.15 to 318.15) K. Pair and higher order volumetric interaction coefficients have been determined by using McMillan-Mayer theory. Partial molar expansion coefficients, (partial derivV{sub 2}{sup 0}/partial derivT){sub p} and the second derivatives (partial deriv{sup 2}V{sub 2}{sup 0}/partial derivT{sup 2}){sub p} have also been estimated. These parameters have been utilized to understand various mixing effects in aqueous solutions due to the interactions between solute (saccharide) and co-solute (sodium acetate).

Reactions of tritium atoms with amino acids, deuterated amino acids and mixtures of amino acids. Additivity property and isotope effect

International Nuclear Information System (INIS)

Badun, G.A.; Filatov, Eh.S.

1988-01-01

Interaction of tritium atoms with glycine (1) and leucine (2) amino acids, deuterated amino acids, their mixtures and glycylleucine (3) peptide in the 77-300 K temperature range is studied in isothermal and gradient regimes. Tagged amino acids were separated from targets after conducting the reaction. At T 150 K are associated with intermolecular transmission of free valence in the mixture of amino acids. Regularities of the reaction found for the mixture of amino acids are conserved for (3) as well, i.e. the peptide bond does not essentially affect the reaction of isotopic exchange conditioned by atomic tritium

The method of quantitative determination of iodine in acetic acid

International Nuclear Information System (INIS)

Sukhomlinov, A.B.; Kalinchenko, N.B.

1988-01-01

Method for separate determination of J 2 and J - concentrations in acetic acid is suggested. Iodine concentration in acetic acid is determined by measuring potential of iodine-selective electrode first in the initial solution of acetic acid, where molecular iodine dissociation equals 0.5, and then in acetic acid, with alkali (NaOH) addition up to pH > 3, where molecular iodine dissociation equals 1. Determination is conducted in 5x10 -7 -5x10 -6 mol/l concentration range with relative standard deviation not more than 0.1. 1 fig

21 CFR 177.1360 - Ethylene-vinyl acetate-vinyl alcohol copolymers.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Ethylene-vinyl acetate-vinyl alcohol copolymers... for Use as Basic Components of Single and Repeated Use Food Contact Surfaces § 177.1360 Ethylene-vinyl acetate-vinyl alcohol copolymers. Ethylene-vinyl acetate-vinyl alcohol copolymers (CAS Reg. No. 26221-27-2...

Gamma amino butyric acid accumulation in medicinal plants without stress.

Science.gov (United States)

Anju, P; Moothedath, Ismail; Rema Shree, Azhimala Bhaskaranpillai

2014-01-01

Gamma amino butyric acid (GABA) is an important ubiquitous four carbon nonprotein amino acid with an amino group attached to gamma carbon instead of beta carbon. It exists in different organisms including bacteria, plants, and animals and plays a crucial role in humans by regulating neuronal excitability throughout the nervous system. It is directly responsible for the regulation of muscle tone and also effective in lowering stress, blood pressure, and hypertension. The aim of the study was to develop the fingerprint profile of selected medicinally and economically important plants having central nervous system (CNS) activity and to determine the quantity of GABA in the selected plants grown under natural conditions without any added stress. The high-performance thin layer chromatography analysis was performed on precoated silica gel plate 60F-254 plate (20 cm × 10 cm) in the form of bands with width 8 mm using Hamilton syringe (100 μl) using n-butanol, acetic acid, and water in the proportion 5:2:2 as mobile phase in a CAMAG chamber which was previously saturated for 30 min. CAMAG TLC scanner 3 was used for the densitometric scanning at 550 nm. Specific marker compounds were used for the quantification. Among the screened medicinal plants, Zingiber officinale and Solanum torvum were found to have GABA. The percentage of GABA present in Z. officinale and S. torvum were found to be 0.0114% and 0.0119%, respectively. The present work confirmed that among the selected CNS active medicinal plants, only two plants contain GABA. We found a negative correlation with plant having CNS activity and accumulation of GABA. The GABA shunt is a conserved pathway in eukaryotes and prokaryotes but, although the role of GABA as a neurotransmitter in mammals is clearly established, its role in plants is still vague.

Process development for the production of 15β-hydroxycyproterone acetate using Bacillus megaterium expressing CYP106A2 as whole-cell biocatalyst

DEFF Research Database (Denmark)

Kiss, Flora M.; Lundemo, Marie Therese; Zapp, Josef

2015-01-01

and drug precursors. Results: In this work, we demonstrate the conversion of a synthetic testosterone derivative, cyproterone acetate, by CYP106A2 under in vitro and in vivo conditions. Using a Bacillus megaterium whole-cell system overexpressing CYP106A2, sufficient amounts of product for structure...... describe the successful scale-up of cyproterone acetate conversion from shake flasks to bioreactors, using the CYP106A2 enzyme in a whole-cell system. The substrate was converted to its main human metabolite, 15 β-hydroxycyproterone acetate, a highly interesting drug candidate, due to its retained...... antiandrogen activity but significantly lower progestogen properties than the mother compound. Optimization of the process led to an improvement from 55% to 98% overall conversion, with a product formation of 0.43 g/L, approaching industrial process requirements and a future large-scale application....

Characterization of acetate transport in colorectal cancer cells and potential therapeutic implications

Science.gov (United States)

Ferro, Suellen; Azevedo-Silva, João; Casal, Margarida; Côrte-Real, Manuela; Baltazar, Fatima; Preto, Ana

2016-01-01

Acetate, together with other short chain fatty acids has been implicated in colorectal cancer (CRC) prevention/therapy. Acetate was shown to induce apoptosis in CRC cells. The precise mechanism underlying acetate transport across CRC cells membrane, that may be implicated in its selectivity towards CRC cells, is not fully understood and was addressed here. We also assessed the effect of acetate in CRC glycolytic metabolism and explored its use in combination with the glycolytic inhibitor 3-bromopyruvate (3BP). We provide evidence that acetate enters CRC cells by the secondary active transporters MCT1 and/or MCT2 and SMCT1 as well as by facilitated diffusion via aquaporins. CRC cell exposure to acetate upregulates the expression of MCT1, MCT4 and CD147, while promoting MCT1 plasma membrane localization. We also observed that acetate increases CRC cell glycolytic phenotype and that acetate-induced apoptosis and anti-proliferative effect was potentiated by 3BP. Our data suggest that acetate selectivity towards CRC cells might be explained by the fact that aquaporins and MCTs are found overexpressed in CRC clinical cases. Our work highlights the importance that acetate transport regulation has in the use of drugs such as 3BP as a new therapeutic strategy for CRC. PMID:28874966

Physicochemical Parameters Affecting the Electrospray Ionization Efficiency of Amino Acids after Acylation

Science.gov (United States)

2017-01-01

Electrospray ionization (ESI) is widely used in liquid chromatography coupled to mass spectrometry (LC–MS) for the analysis of biomolecules. However, the ESI process is still not completely understood, and it is often a matter of trial and error to enhance ESI efficiency and, hence, the response of a given set of compounds. In this work we performed a systematic study of the ESI response of 14 amino acids that were acylated with organic acid anhydrides of increasing chain length and with poly(ethylene glycol) (PEG) changing certain physicochemical properties in a predictable manner. By comparing the ESI response of 70 derivatives, we found that there was a strong correlation between the calculated molecular volume and the ESI response, while correlation with hydrophobicity (log P values), pKa, and the inverse calculated surface tension was significantly lower although still present, especially for individual derivatized amino acids with increasing acyl chain lengths. Acylation with PEG containing five ethylene glycol units led to the largest gain in ESI response. This response was maximal independent of the calculated physicochemical properties or the type of amino acid. Since no actual physicochemical data is available for most derivatized compounds, the responses were also used as input for a quantitative structure–property relationship (QSPR) model to find the best physicochemical descriptors relating to the ESI response from molecular structures using the amino acids and their derivatives as a reference set. A topological descriptor related to molecular size (SPAN) was isolated next to a descriptor related to the atomic composition and structural groups (BIC0). The validity of the model was checked with a test set of 43 additional compounds that were unrelated to amino acids. While prediction was generally good (R2 > 0.9), compounds containing halogen atoms or nitro groups gave a lower predicted ESI response. PMID:28737384

The remarkable stability of chimeric, sialic acid-derived alpha/delta-peptides in human blood plasma.

Science.gov (United States)

Saludes, Jonel P; Natarajan, Arutselvan; DeNardo, Sally J; Gervay-Hague, Jacquelyn

2010-05-01

Peptides are labile toward proteolytic enzymes, and structural modifications are often required to prolong their metabolic half-life and increase resistance. One modification is the incorporation of non-alpha-amino acids into the peptide to deter recognition by hydrolytic enzymes. We previously reported the synthesis of chimeric alpha/delta-peptides from glutamic acids (Glu) and the sialic acid derivative Neu2en. Conformational analyses revealed these constructs adopt secondary structures in water and may serve as conformational surrogates of polysialic acid. Polysialic acid is a tumor-associated polysaccharide and is correlated with cancer metastasis. Soluble polysialic acid is rapidly cleared from the blood limiting its potential for vaccine development. One motivation in developing structural surrogates of polysialic acid was to create constructs with increased bioavailability. Here, we report plasma stability profiles of Glu/Neu2en alpha/delta-peptides. DOTA was conjugated at the peptide N-termini by solid phase peptide synthesis, radiolabeled with (111)In, incubated in human blood plasma at 37 degrees C, and their degradation patterns monitored by cellulose acetate electrophoresis and radioactivity counting. Results indicate that these peptides exhibit a long half-life that is two- to three-orders of magnitude higher than natural alpha-peptides. These findings provide a viable platform for the synthesis of plasma stable, sialic acid-derived peptides that may find pharmaceutical application.

11C-acetate PET imaging in patients with multiple sclerosis.

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Kazushiro Takata

Full Text Available BACKGROUND: Activation of glial cells is a cardinal feature in multiple sclerosis (MS pathology, and acetate has been reported to be selectively uptaken by astrocytes in the CNS. The aim of this study was to investigate the efficacy of PET with (11C-acetate for MS diagnosis. MATERIALS AND METHODS: Six patients with relapsing-remitting MS and 6 healthy volunteers (HV were enrolled. The (11C-acetate brain uptake on PET was measured in patients with MS and HV. Volume-of-interest analysis of cerebral gray and white matter based on the segmentation technique for co-registered MRI and voxel-based statistical parametric analysis were performed. Correlation between 11C-acetate uptake and the lesion number in T1- and T2- weighted MR images were also assessed. RESULTS: The standardized uptake value (SUV of 11C-acetate was increased in both white and gray matter in MS patients compared to HV. Voxel-based statistical analysis revealed a significantly increased SUV relative to that in the bilateral thalami (SUVt in a broad area of white matter, particularly in the subcortical white matter of MS patients. The numbers of T2 lesions and T1 black holes were significantly correlated with SUV of (11C-acetate in white and gray matter. CONCLUSIONS: The 11C-acetate uptake significantly increased in MS patients and correlated to the number of MRI lesions. These preliminary data suggest that (11C-acetate PET can be a useful clinical examination for MS patients.

Acetate transiently inhibits myocardial contraction by increasing mitochondrial calcium uptake.

Science.gov (United States)

Schooley, James F; Namboodiri, Aryan M A; Cox, Rachel T; Bünger, Rolf; Flagg, Thomas P

2014-12-09

There is a close relationship between cardiovascular disease and cardiac energy metabolism, and we have previously demonstrated that palmitate inhibits myocyte contraction by increasing Kv channel activity and decreasing the action potential duration. Glucose and long chain fatty acids are the major fuel sources supporting cardiac function; however, cardiac myocytes can utilize a variety of substrates for energy generation, and previous studies demonstrate the acetate is rapidly taken up and oxidized by the heart. In this study, we tested the effects of acetate on contractile function of isolated mouse ventricular myocytes. Acute exposure of myocytes to 10 mM sodium acetate caused a marked, but transient, decrease in systolic sarcomere shortening (1.49 ± 0.20% vs. 5.58 ± 0.49% in control), accompanied by a significant increase in diastolic sarcomere length (1.81 ± 0.01 μm vs. 1.77 ± 0.01 μm in control), with a near linear dose response in the 1-10 mM range. Unlike palmitate, acetate caused no change in action potential duration; however, acetate markedly increased mitochondrial Ca(2+) uptake. Moreover, pretreatment of cells with the mitochondrial Ca(2+) uptake blocker, Ru-360 (10 μM), markedly suppressed the effect of acetate on contraction. Lehninger and others have previously demonstrated that the anions of weak aliphatic acids such as acetate stimulate Ca(2+) uptake in isolated mitochondria. Here we show that this effect of acetate appears to extend to isolated cardiac myocytes where it transiently modulates cell contraction.

Highly Efficient Catalytic Synthesis of α-Amino Acids under Phase-Transfer Conditions with a Novel Catalyst/Substrate Pair

NARCIS (Netherlands)

Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Larionov, Oleg V.; Harutyunyan, Syuzanna R.; Vyskočil, Štepán; North, Michael; Kagan, Henri B.

2001-01-01

A facile and fast enantioselective synthesis of α-amino acids with high ee values was achieved by the asymmetric alkylation of the glycine derivative under phase-transfer conditions with (R)- or (S)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN). The ee value of the catalyst can be as little as 40 %

Elevational Variation in Soil Amino Acid and Inorganic Nitrogen Concentrations in Taibai Mountain, China.

Directory of Open Access Journals (Sweden)

Xiaochuang Cao

Full Text Available Amino acids are important sources of soil organic nitrogen (N, which is essential for plant nutrition, but detailed information about which amino acids predominant and whether amino acid composition varies with elevation is lacking. In this study, we hypothesized that the concentrations of amino acids in soil would increase and their composition would vary along the elevational gradient of Taibai Mountain, as plant-derived organic matter accumulated and N mineralization and microbial immobilization of amino acids slowed with reduced soil temperature. Results showed that the concentrations of soil extractable total N, extractable organic N and amino acids significantly increased with elevation due to the accumulation of soil organic matter and the greater N content. Soil extractable organic N concentration was significantly greater than that of the extractable inorganic N (NO3--N + NH4+-N. On average, soil adsorbed amino acid concentration was approximately 5-fold greater than that of the free amino acids, which indicates that adsorbed amino acids extracted with the strong salt solution likely represent a potential source for the replenishment of free amino acids. We found no appreciable evidence to suggest that amino acids with simple molecular structure were dominant at low elevations, whereas amino acids with high molecular weight and complex aromatic structure dominated the high elevations. Across the elevational gradient, the amino acid pool was dominated by alanine, aspartic acid, glycine, glutamic acid, histidine, serine and threonine. These seven amino acids accounted for approximately 68.9% of the total hydrolyzable amino acid pool. The proportions of isoleucine, tyrosine and methionine varied with elevation, while soil major amino acid composition (including alanine, arginine, aspartic acid, glycine, histidine, leucine, phenylalanine, serine, threonine and valine did not vary appreciably with elevation (p>0.10. The compositional

Proteome analysis of Acetobacter pasteurianus during acetic acid fermentation.

Science.gov (United States)

Andrés-Barrao, Cristina; Saad, Maged M; Chappuis, Marie-Louise; Boffa, Mauro; Perret, Xavier; Ortega Pérez, Ruben; Barja, François

2012-03-16

Acetic acid bacteria (AAB) are Gram-negative, strictly aerobic microorganisms that show a unique resistance to ethanol (EtOH) and acetic acid (AcH). Members of the Acetobacter and Gluconacetobacter genera are capable of transforming EtOH into AcH via the alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) enzymes and are used for the industrial production of vinegar. Several mechanisms have been proposed to explain how AAB resist high concentrations of AcH, such as the assimilation of acetate through the tricarboxylic acid (TCA) cycle, the export of acetate by various transporters and modifications of the outer membrane. However, except for a few acetate-specific proteins, little is known about the global proteome responses to AcH. In this study, we used 2D-DIGE to compare the proteome of Acetobacter pasteurianus LMG 1262(T) when growing in glucose or ethanol and in the presence of acetic acid. Interesting protein spots were selected using the ANOVA p-value of 0.05 as threshold and 1.5-fold as the minimal level of differential expression, and a total of 53 proteins were successfully identified. Additionally, the size of AAB was reduced by approximately 30% in length as a consequence of the acidity. A modification in the membrane polysaccharides was also revealed by PATAg specific staining. Copyright © 2011 Elsevier B.V. All rights reserved.

Development of Acetic Acid Removal Technology for the UREX+Process

International Nuclear Information System (INIS)

Counce, Robert M.; Watson, Jack S.

2009-01-01

It is imperative that acetic acid is removed from a waste stream in the UREX+process so that nitric acid can be recycled and possible interference with downstream steps can be avoided. Acetic acid arises from acetohydrozamic acid (AHA), and is used to suppress plutonium in the first step of the UREX+process. Later, it is hydrolyzed into hydroxyl amine nitrate and acetic acid. Many common separation technologies were examined, and solvent extraction was determined to be the best choice under process conditions. Solvents already used in the UREX+ process were then tested to determine if they would be sufficient for the removal of acetic acid. The tributyl phosphage (TBP)-dodecane diluent, used in both UREX and NPEX, was determined to be a solvent system that gave sufficient distribution coefficients for acetic acid in addition to a high separation factor from nitric acid

Development of Acetic Acid Removal Technology for the UREX+Process

Energy Technology Data Exchange (ETDEWEB)

Robert M. Counce; Jack S. Watson

2009-06-30

It is imperative that acetic acid is removed from a waste stream in the UREX+process so that nitric acid can be recycled and possible interference with downstreatm steps can be avoidec. Acetic acid arises from acetohydrozamic acid (AHA), and is used to suppress plutonium in the first step of the UREX+process. Later, it is hydrolyzed into hydroxyl amine nitrate and acetic acid. Many common separation technologies were examined, and solvent extraction was determined to be the best choice under process conditions. Solvents already used in the UREX+ process were then tested to determine if they would be sufficient for the removal of acetic acid. The tributyl phosphage (TBP)-dodecane diluent, used in both UREX and NPEX, was determined to be a solvent system that gave sufficient distribution coefficients for acetic acid in addition to a high separation factor from nitric acid.

Mechanistic Insights on C-O and C-C Bond Activation and Hydrogen Insertion during Acetic Acid Hydrogenation Catalyzed by Ruthenium Clusters in Aqueous Medium

Energy Technology Data Exchange (ETDEWEB)

Shangguan, Junnan; Olarte, Mariefel V.; Chin, Ya-Huei [Cathy

2016-06-07

Catalytic pathways for acetic acid (CH3COOH) and hydrogen (H2) reactions on dispersed Ru clusters in the aqueous medium and the associated kinetic requirements for C-O and C-C bond cleavages and hydrogen insertion are established from rate and isotopic assessments. CH3COOH reacts with H2 in steps that either retain its carbon backbone and lead to ethanol, ethyl acetate, and ethane (47-95 %, 1-23 %, and 2-17 % carbon selectivities, respectively) or break its C-C bond and form methane (1-43 % carbon selectivities) at moderate temperatures (413-523 K) and H2 pressures (10-60 bar, 298 K). Initial CH3COOH activation is the kinetically relevant step, during which CH3C(O)-OH bond cleaves on a metal site pair at Ru cluster surfaces nearly saturated with adsorbed hydroxyl (OH*) and acetate (CH3COO*) intermediates, forming an adsorbed acetyl (CH3CO*) and hydroxyl (OH*) species. Acetic acid turnover rates increase proportionally with both H2 (10-60 bar) and CH3COOH concentrations at low CH3COOH concentrations (<0.83 M), but decrease from first to zero order as the CH3COOH concentration and the CH3COO* coverages increase and the vacant Ru sites concomitantly decrease. Beyond the initial CH3C(O)-OH bond activation, sequential H-insertions on the surface acetyl species (CH3CO*) lead to C2 products and their derivative (ethanol, ethane, and ethyl acetate) and the competitive C-C bond cleavage of CH3CO* causes the eventual methane formation. The instantaneous carbon selectivities towards C2 species (ethanol, ethane, and ethyl acetate) increase linearly with the concentration of proton-type Hδ+ (derived from carboxylic acid dissociation) and chemisorbed H*. The selectivities towards C2 products decrease with increasing temperature, because of higher observed barriers for C-C bond cleavage than H-insertion. This study offers an interpretation of mechanism and energetics and provides kinetic evidence of carboxylic acid assisted proton-type hydrogen (Hδ+) shuffling during H

Acetic acid sclerotheraphy of renal cysts

International Nuclear Information System (INIS)

Hong, Hoon Pyo; Oh, Joo Hyeong; Yoon, Yup; Kong, Keun Young; Kim, Eui Jong; Goo, Jang Sung

1998-01-01

Sclerotherapy for renal cysts was performed, using 50% acetic acid as new sclerosing agent. We report the methods and results of this procedure. Fifteen patients underwent sclerotherapy for renal cyst, using 50% acetic acid. Because four patients were lost to follow-up, only 11 of the 15 were included in this study. The renal cysts, including one infected case, were diagnosed by ultrasonograpy (n=3D10) ormagnetic resonance imaging (n=3D1). The patient group consisted of four men and seven women(mean age, 59 years; range, 23-77). At first, the cyst was completely aspirated, and 25 volume% of aspirated volume was replaced with 50% sterile acetic acid through the drainage catheter. During the follwing 20 minutes, the patient changed position, and the acetic acid was then removed from the cyst. Finally, the drainage catheter was removed, after cleaning the cyst with saline. After treatment of infection by antibiotics and catheter drainage for 7 days, sclerotherapy in the infected case followed the same procedure. In order to observe changes in the size of renal cysts and recurrence, all patients were followed up by ultrasound between 2 and 8 months. We defined response to therapy as follows:complete regression as under 5 volume%, partial regression as 5-50 volume% and no response as more than 50 volume% of initial cyst volume. No clinically significant complication occured during the procedures or follow-up periods. All cysts regressed completely during follow-up of 8 months. Complete regression occurred as follows: two cysts at 2 months, seven cysts at 4 months, two cysts at 6 months. Two cysts showed residues at the last follow-up, at 4 and 6 months, respectively. The volume of residual cysts decreased to under 5 volume% of initial volume, however. Completely regressed cysts did not recurr during follow-up. Acetic acid sclerotherapy for renal cysts showed good results, regardless of the dilution of sclerosing agent with residual cyst fluid, and no significant