WorldWideScience

Sample records for biomimetic total synthesis

  1. A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A

    OpenAIRE

    McDonald, Benjamin R.; Nibbs, Antoinette E.; Scheidt, Karl A.

    2014-01-01

    We report the first asymmetric, total synthesis of (−)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

  2. Total Synthesis of (+)-Cytosporolide A via a Biomimetic Hetero-Diels-Alder Reaction.

    Science.gov (United States)

    Takao, Ken-Ichi; Noguchi, Shuji; Sakamoto, Shu; Kimura, Mizuki; Yoshida, Keisuke; Tadano, Kin-Ichi

    2015-12-23

    The first total synthesis of (+)-cytosporolide A was achieved by a biomimetic hetero-Diels-Alder reaction of (-)-fuscoatrol A with o-quinone methide generated from (+)-CJ-12,373. The dienophile, highly oxygenated caryophyllene sesquiterpenoid (-)-fuscoatrol A, was synthesized from the synthetic intermediate in our previous total synthesis of (+)-pestalotiopsin A. The o-quinone methide precursor, isochroman carboxylic acid (+)-CJ-12,373, was synthesized through a Kolbe-Schmitt reaction and an oxa-Pictet-Spengler reaction. The hetero-Diels-Alder reaction of these two compounds proceeded with complete chemo-, regio-, and stereoselectivity to produce the complicated pentacyclic ring system of the cytosporolide skeleton. This total synthesis unambiguously demonstrates that natural cytosporolide A has the structure previously suggested. PMID:26633257

  3. Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor

    Science.gov (United States)

    A new prenylated indole alkaloid, versicolamide B, was isolated from cultures of Aspergillus versicolor NRRL 35600. The structure was assigned by 2D NMR data, and confirmed by a biomimetic total synthesis. Versicolamide B is the first member of the paraherquamide-stephacidin family of alkaloids fo...

  4. Biomimetic thin film synthesis

    Energy Technology Data Exchange (ETDEWEB)

    Graff, G.L.; Campbell, A.A.; Gordon, N.R.

    1995-05-01

    The purpose of this program is to develop a new process for forming thin film coatings and to demonstrate that the biomimetic thin film technology developed at PNL is useful for industrial applications. In the biomimetic process, mineral deposition from aqueous solution is controlled by organic functional groups attached to the underlying substrate surface. The coatings process is simple, benign, inexpensive, energy efficient, and particularly suited for temperature sensitive substrate materials (such as polymers). In addition, biomimetic thin films can be deposited uniformly on complex shaped and porous substrates providing a unique capability over more traditional line-of-sight methods.

  5. BIOMIMETIC STRATEGIES IN ORGANIC SYNTHESIS. TERPENES

    OpenAIRE

    V. Kulcitki

    2012-01-01

    The current paper represents an outline of the selected contributions to the biomimetic procedures and approaches for the synthesis of terpenes with complex structure and diverse functionalisation pattern. These include homologation strategies, cyclisations, rearrangements, as well as biomimetic remote functionalisations.

  6. BIOMIMETIC STRATEGIES IN ORGANIC SYNTHESIS. TERPENES

    Directory of Open Access Journals (Sweden)

    V. Kulcitki

    2012-12-01

    Full Text Available The current paper represents an outline of the selected contributions to the biomimetic procedures and approaches for the synthesis of terpenes with complex structure and diverse functionalisation pattern. These include homologation strategies, cyclisations, rearrangements, as well as biomimetic remote functionalisations.

  7. Biomimetic, Catalytic Oxidation in Organic Synthesis

    Institute of Scientific and Technical Information of China (English)

    Shun-lchi Murahashi

    2005-01-01

    @@ 1Introduction Oxidation is one of the most fundamental reactions in organic synthesis. Owing to the current need to develop forward-looking technology that is environmentally acceptable with respect many aspects. The most attractive approaches are biomimetic oxidation reactions that are closely related to the metabolism of living things. The metabolisms are governed by a variety of enzymes such as cytochrome P-450 and flavoenzyme.Simulation of the function of these enzymes with simple transition metal complex catalyst or organic catalysts led to the discovery of biomimetic, catalytic oxidations with peroxides[1]. We extended such biomimetic methods to the oxidation with molecular oxygen under mild conditions.

  8. Biomimetic synthesis for precursor of muscone

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Muscone is a precious fragrant compound scarce in nature. Many attempts have been made to synthesize this unique natural product. In this work, the one- carbon unit transfer reaction of tetrahydrofolate coenzyme was initiated. Benzimidazolium salt was used as the tetrahydrofolate coenzyme model at formic acid oxidation level and di-Grignard reagent as the nucleophile to which one-carbon unit was transferred; the biomimetic synthesis of 2,15- hexade-canedione, a precursor of muscone, was successfully accomplished by using the addition-hydrolysis reaction of benzimidazolium salt with Grignard reagent. And an impor-tant useful method for the synthesis of muscone is provided.

  9. First total synthesis of Boehmenan

    Indian Academy of Sciences (India)

    Yamu Xia; Xiaoli Dai; Haixin Liu; Chen Chai

    2014-05-01

    The first total synthesis of dilignan Boehmenan has been achieved. A biomimetic oxidative coupling of the ferulic acid methyl ester in the presence of silver oxide is the crucial step in the synthesis sequence, generating the dihydrobenzofuran skeleton. Hydroxyl group was protected with DHP and reducted with LiAlH4 to afford the intermediate diol. The diol was condensated with the derivative of ferulic acid, then removed the protecting groups, to get Boehmenan. Meanwhile, a study on the ring-opening reaction of the intermediate dihydrobenzofuran neolignan under base conditions was described.

  10. Stereocontrolled total synthesis of hedyotol A.

    Science.gov (United States)

    Kawabe, Yusuke; Ishikawa, Ryo; Akao, Yusuke; Yoshida, Atsushi; Inai, Makoto; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki

    2014-04-01

    The total synthesis of hedyotol A (1), a natural product isolated from Hedyotis lawsoniae (DC.) Wight et Arn. (Rubiaceae), was accomplished in a highly stereocontrolled manner. Key steps include an L-proline-catalyzed cross-aldol reaction and the biomimetic construction of a furofuran lignan skeleton through a quinomethide intermediate. PMID:24660822

  11. Total synthesis of atropurpuran.

    Science.gov (United States)

    Gong, Jing; Chen, Huan; Liu, Xiao-Yu; Wang, Zhi-Xiu; Nie, Wei; Qin, Yong

    2016-01-01

    Due to their architectural intricacy and biological significance, the synthesis of polycyclic diterpenes and their biogenetically related alkaloids have been the subject of considerable interest over the last few decades, with progress including the impressive synthesis of several elusive targets. Despite tremendous efforts, conquering the unique structural types of this large natural product family remains a long-term challenge. The arcutane diterpenes and related alkaloids, bearing a congested tetracyclo[5.3.3.0(4,9).0(4,12)]tridecane unit, are included in these unsolved enigmas. Here we report a concise approach to the construction of the core structure of these molecules and the first total synthesis of (±)-atropurpuran. Pivotal features of the synthesis include an oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade, sequential aldol and ketyl-olefin cyclizations to assemble the highly caged framework, and a chemoselective and stereoselective reduction to install the requisite allylic hydroxyl group in the target molecule. PMID:27387707

  12. Total Synthesis of Naloxone

    Institute of Scientific and Technical Information of China (English)

    HU Wen-Xiang; WANG Jian-Ying; XU Ming

    2003-01-01

    @@ Naloxone (1) is one of the 14-hydroxyl substituted opium antagonists which are valuable medications for treat ment of opiate abuse, opiate overdose, and alcohol addiction. Here, the total synthesis of naloxone was described. We selected 2,6-dihydroxynaphalene (2) as the starting material.

  13. Bottom-Up Synthesis and Sensor Applications of Biomimetic Nanostructures

    Directory of Open Access Journals (Sweden)

    Li Wang

    2016-01-01

    Full Text Available The combination of nanotechnology, biology, and bioengineering greatly improved the developments of nanomaterials with unique functions and properties. Biomolecules as the nanoscale building blocks play very important roles for the final formation of functional nanostructures. Many kinds of novel nanostructures have been created by using the bioinspired self-assembly and subsequent binding with various nanoparticles. In this review, we summarized the studies on the fabrications and sensor applications of biomimetic nanostructures. The strategies for creating different bottom-up nanostructures by using biomolecules like DNA, protein, peptide, and virus, as well as microorganisms like bacteria and plant leaf are introduced. In addition, the potential applications of the synthesized biomimetic nanostructures for colorimetry, fluorescence, surface plasmon resonance, surface-enhanced Raman scattering, electrical resistance, electrochemistry, and quartz crystal microbalance sensors are presented. This review will promote the understanding of relationships between biomolecules/microorganisms and functional nanomaterials in one way, and in another way it will guide the design and synthesis of biomimetic nanomaterials with unique properties in the future.

  14. Total Synthesis of Millingtonine.

    Science.gov (United States)

    Brown, Patrick D; Lawrence, Andrew L

    2016-07-11

    Millingtonine is a glycosidic alkaloid that exists as a pair of pseudo-enantiomeric diastereomers. Consideration of the likely biosynthetic origins of this unusual natural product has resulted in the development of a seven-step total synthesis. Results from this synthetic work provide evidence in support of a proposed network of biosynthetic pathways that can account for the formation of several phenylethanoid natural products. PMID:27249628

  15. Total synthesis of teixobactin

    Science.gov (United States)

    Jin, Kang; Sam, Iek Hou; Po, Kathy Hiu Laam; Lin, Du'an; Ghazvini Zadeh, Ebrahim H.; Chen, Sheng; Yuan, Yu; Li, Xuechen

    2016-08-01

    To cope with the global bacterial multidrug resistance, scientific communities have devoted significant efforts to develop novel antibiotics, particularly those with new modes of actions. Teixobactin, recently isolated from uncultured bacteria, is considered as a promising first-in-class drug candidate for clinical development. Herein, we report its total synthesis by a highly convergent Ser ligation approach and this strategy allows us to prepare several analogues of the natural product.

  16. Total synthesis of teixobactin.

    Science.gov (United States)

    Jin, Kang; Sam, Iek Hou; Po, Kathy Hiu Laam; Lin, Du'an; Ghazvini Zadeh, Ebrahim H; Chen, Sheng; Yuan, Yu; Li, Xuechen

    2016-01-01

    To cope with the global bacterial multidrug resistance, scientific communities have devoted significant efforts to develop novel antibiotics, particularly those with new modes of actions. Teixobactin, recently isolated from uncultured bacteria, is considered as a promising first-in-class drug candidate for clinical development. Herein, we report its total synthesis by a highly convergent Ser ligation approach and this strategy allows us to prepare several analogues of the natural product. PMID:27484680

  17. Total synthesis of ochnaflavone

    OpenAIRE

    Monica M. Ndoile; van Heerden, Fanie R

    2013-01-01

    The first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

  18. Total synthesis of ochnaflavone

    Directory of Open Access Journals (Sweden)

    Monica M. Ndoile

    2013-07-01

    Full Text Available The first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

  19. Biomimetics

    Indian Academy of Sciences (India)

    P Ramachandra Rao

    2003-06-01

    The well-organised multifunctional structures, systems and biogenic materials found in nature have attracted the interest of scientists working in many disciplines. The efforts have resulted in the development of a new and rapidly growing field of scientific effort called biomimetics. In this article we present a few natural materials and systems and explore how ideas from nature are being interpreted and modified to suit efforts aimed at designing better machines and synthesising newer materials.

  20. Total Synthesis of (-)-Daphenylline.

    Science.gov (United States)

    Yamada, Ryosuke; Adachi, Yohei; Yokoshima, Satoshi; Fukuyama, Tohru

    2016-05-10

    Total synthesis of (-)-daphenylline, a hexacyclic Daphniphyllum alkaloid, was achieved. Construction of the tricyclic DEF ring system was initiated by asymmetric Negishi coupling followed by an intramolecular Friedel-Crafts reaction. Installation of a side chain onto the tricyclic core was carried out through Sonogashira coupling, stereocontrolled Claisen rearrangement by taking advantage of the characteristic conformation of the tricyclic DEF core, and the stereoselective alkylation of a lactone. After the introduction of a glycine unit, the ABC ring system was stereoselectively constructed through intramolecular cycloaddition of the cyclic azomethine ylide. PMID:27062676

  1. Methods for Improving Enzymatic Trans-glycosylation for Synthesis of Human Milk Oligosaccharide Biomimetics

    DEFF Research Database (Denmark)

    Zeuner, Birgitte; Jers, Carsten; Mikkelsen, Jørn Dalgaard;

    2014-01-01

    Recently, significant progress has been made within enzymatic synthesis of biomimetic, functional glycans, including, for example, human milk oligosaccharides. These compounds are mainly composed of N-acetylglucosamine, fucose, sialic acid, galactose, and glucose, and their controlled enzymatic...

  2. Dihydrobenzofuran Neolignanamides: Laccase-Mediated Biomimetic Synthesis and Antiproliferative Activity.

    Science.gov (United States)

    Cardullo, Nunzio; Pulvirenti, Luana; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele Filippo; Tringali, Corrado

    2016-08-26

    The biomimetic synthesis of a small library of dihydrobenzofuran neolignanamides (the natural trans-grossamide (4) and the related compounds 21-28) has been carried out through an eco-friendly oxidative coupling reaction mediated by Trametes versicolor laccase. These products, after complete spectroscopic characterization, were evaluated for their antiproliferative activity against Caco-2 (colon carcinoma), MCF-7 (mammary adenocarcinoma), and PC-3 (prostate cancer) human cells, using an MTT bioassay. The racemic neolignamides (±)-21 and (±)-27, in being the most lipophilic in the series, were potently active, with GI50 values comparable to or even lower than that of the positive control 5-FU. The racemates were resolved through chiral HPLC, and the pure enantiomers were subjected to ECD measurements to establish their absolute configurations at C-2 and C-3. All enantiomers showed potent antiproliferative activity, with, in particular, a GI50 value of 1.1 μM obtained for (2R,3R)-21. The effect of (±)-21 on the Caco-2 cell cycle was evaluated by flow cytometry, and it was demonstrated that (±)-21 exerts its antiproliferative activity by inducing cell cycle arrest and apoptosis. PMID:27504537

  3. Biomimetic Synthesis of Calcium-Deficient Hydroxyapatite in a Natural Hydrogel

    Energy Technology Data Exchange (ETDEWEB)

    Hutchens, Stacy A [ORNL; Benson, Roberto S. [University of Tennessee, Knoxville (UTK); Evans, Barbara R [ORNL; O' Neill, Hugh Michael [ORNL; Rawn, Claudia J [ORNL

    2006-01-01

    A novel composite material consisting of calcium-deficient hydroxyapatite (CdHAP) biomimetically deposited in a bacterial cellulose hydrogel was synthesized and characterized. Cellulose produced by Gluconacetobacter hansenii was purified and sequentially incubated in solutions of calcium chloride followed by sodium phosphate dibasic. A substantial amount of apatite (50-90% of total dry weight) was homogeneously incorporated throughout the hydrogel after this treatment. X-ray diffractometry (XRD) showed that CdHAP crystallites had formed in the cellulose. XRD further demonstrated that the CdHAP was comprised of 10-50nm anisotropic crystallites elongated in the c-axis, similar to natural bone apatite. Fourier transform infrared (FTIR) spectroscopy demonstrated that hydroxyl IR bands of the cellulose shifted to lower wave numbers indicating that a coordinate bond had possibly formed between the CdHAP and the cellulose hydroxyl groups. FTIR also suggested that the CdHAP had formed from an octacalcium phosphate precursor similar to physiological bone. Scanning electron microscopy (SEM) images confirmed that uniform ?1 mm spherical CdHAP particles comprised of nanosized crystallites with a lamellar morphology had formed in the cellulose. The synthesis of the composite mimics the natural biomineralization of bone indicating that bacterial cellulose can be used as a template for biomimetic apatite formation. This composite may have potential use as an orthopedic biomaterial.

  4. Diastereoselective Total Synthesis of (-)-Galiellalactone.

    Science.gov (United States)

    Kim, Taewoo; Han, Young Taek; An, Hongchan; Kim, Kyeojin; Lee, Jeeyeon; Suh, Young-Ger

    2015-12-18

    An enantioselective total synthesis of (-)-galiellalactone has been accomplished. The key features of the synthesis involve the highly stereoselective construction of the cis-trisubstituted cyclopentane intermediate by a Pd(0)-catalyzed cyclization, the stereospecific introduction of an angular hydroxyl group by Riley oxidation, and the efficient construction of the tricyclic system of (-)-galiellalactone via a combination of diastereoselective Hosomi-Sakurai crotylation and ring-closing metathesis (RCM). PMID:26544529

  5. Biomimetic 'Green' Synthesis of Nanomaterials Using Antioxidants-Vitamins, Glutathione and Polyphenols from Tea and Wine

    Science.gov (United States)

    The presentation summarizes our recent activity in chemical synthesis of nanomaterials via benign biomimetic ‘greener’ alternatives,1 such as the use antioxidants present in a variety of natural products, and ubiquitous glutathione in aqueous media.2 Vitamins B1, B2, C, and tea ...

  6. Biomimetic flavin-catalysed reactions for organic synthesis.

    Science.gov (United States)

    Iida, H; Imada, Y; Murahashi, S-I

    2015-07-28

    Using simple riboflavin related compounds as biomimetic catalysts, catalytic oxidation of various substrates with hydrogen peroxide or molecular oxygen can be performed selectively under mild conditions. The principle of these reactions is fundamental and will provide a wide scope for environmentally benign future practical methods.

  7. Stereoselective Total Synthesis of Mycalamides

    Institute of Scientific and Technical Information of China (English)

    Masahiro Toyota

    2005-01-01

    @@ 1Introduction Mycalamides A (1a) and B (1b) are potent antiviral compounds from a New Zealand sponge of the genus Mycale. Apart from their antitumor property, mycalamide A (1a) exhibits immunosuppressive action by blocking T-cell activation in mice and is significantly more potent than FK-506 and cyclosporine A. Because of their intriguing biological activity, unique structures and scarce supply of these natural products, mycalamides A (1a) and B (1b) have attracted considerable attention as target molecules for total synthesis, and total, formal, or partial syntheses of this family of compounds have been reported[1,2].

  8. A bio-inspired total synthesis of tetrahydrofuran lignans.

    Science.gov (United States)

    Albertson, Anna K F; Lumb, Jean-Philip

    2015-02-01

    Lignan natural products comprise a broad spectrum of biologically active secondary metabolites. Their structural diversity belies a common biosynthesis, which involves regio- and chemoselective oxidative coupling of propenyl phenols. Attempts to replicate this oxidative coupling have revealed significant challenges for controlling selectivity, and these challenges have thus far prevented the development of a unified biomimetic route to compounds of the lignan family. A practical solution is presented that hinges on oxidative ring opening of a diarylcyclobutane to intercept a putative biosynthetic intermediate. The effectiveness of this approach is demonstrated by the first total synthesis of tanegool in 4 steps starting from ferulic acid, as well as a concise synthesis of the prototypical furanolignan pinoresinol.

  9. The total synthesis of (-)-nitidasin.

    Science.gov (United States)

    Hog, Daniel T; Huber, Florian M E; Mayer, Peter; Trauner, Dirk

    2014-08-01

    Nitidasin is a pentacyclic sesterterpenoid with a rare 5-8-6-5 carbon skeleton that was isolated from the Peruvian folk medicine "Hercampuri". It belongs to a small class of sesterterpenoids that feature an isopropyl trans-hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans-hydrindanone, followed by chemoselective epoxidation, ring-closing olefin metathesis, and redox adjustment.

  10. Biomimetic synthesis of calcium-strontium apatite hollow nanospheres

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    In this work,calcium-strontium apatite (Sr-HA) hollow nanospheres were synthesized by a facile biomimetic method.The structure and property of Sr-HA were characterized by FESEM,TEM,HRTEM,XRD and FT-IR spectroscopy.The influences of different ratios of calcium and strontium on the morphologies of the Sr-HA products were investigated.The experimental results revealed that the hollow spherical Sr-HA,with a size of 30-120 nm in diameter,could be synthesized when the molar ratio of Ca/Sr was 1:1.The possible formation mechanism of the hollow Sr-HA was proposed.The drug release experiments indicated that the hollow spherical Sr-HA had the property of sustained release.

  11. Biomimetic self-cleaning surfaces: synthesis, mechanism and applications.

    Science.gov (United States)

    Xu, Quan; Zhang, Wenwen; Dong, Chenbo; Sreeprasad, Theruvakkattil Sreenivasan; Xia, Zhenhai

    2016-09-01

    With millions of years of natural evolution, organisms have achieved sophisticated structures, patterns or textures with complex, spontaneous multifunctionality. Among all the fascinating characteristics observed in biosystems, self-cleaning ability is regarded as one of the most interesting topics in biomimicry because of its potential applications in various fields such as aerospace, energy conversion and biomedical and environmental protection. Recently, in-depth studies have been carried out on various compelling biostructures including lotus leaves, shark skins, butterfly wings and gecko feet. To understand and mimic their self-cleaning mechanisms in artificial structures, in this article, recent progress in self-cleaning techniques is discussed and summarized. Based on the underlying self-cleaning mechanisms, the methods are classified into two categories: self-cleaning with water and without water. The review gives a succinct account of the detailed mechanisms and biomimetic processes applied to create artificial self-cleaning materials and surfaces, and provides some examples of cutting-edge applications such as anti-reflection, water repellence, self-healing, anti-fogging and micro-manipulators. The prospectives and directions of future development are also briefly proposed.

  12. Biomimetic self-cleaning surfaces: synthesis, mechanism and applications.

    Science.gov (United States)

    Xu, Quan; Zhang, Wenwen; Dong, Chenbo; Sreeprasad, Theruvakkattil Sreenivasan; Xia, Zhenhai

    2016-09-01

    With millions of years of natural evolution, organisms have achieved sophisticated structures, patterns or textures with complex, spontaneous multifunctionality. Among all the fascinating characteristics observed in biosystems, self-cleaning ability is regarded as one of the most interesting topics in biomimicry because of its potential applications in various fields such as aerospace, energy conversion and biomedical and environmental protection. Recently, in-depth studies have been carried out on various compelling biostructures including lotus leaves, shark skins, butterfly wings and gecko feet. To understand and mimic their self-cleaning mechanisms in artificial structures, in this article, recent progress in self-cleaning techniques is discussed and summarized. Based on the underlying self-cleaning mechanisms, the methods are classified into two categories: self-cleaning with water and without water. The review gives a succinct account of the detailed mechanisms and biomimetic processes applied to create artificial self-cleaning materials and surfaces, and provides some examples of cutting-edge applications such as anti-reflection, water repellence, self-healing, anti-fogging and micro-manipulators. The prospectives and directions of future development are also briefly proposed. PMID:27628170

  13. Total Synthesis of Chiral Biaryl Natural Products by Asymmetric Biaryl Coupling ‡

    OpenAIRE

    Kozlowski, Marisa C.; Morgan, Barbara J.; Linton, Elizabeth C.

    2009-01-01

    This tutorial review highlights the use of catalytic asymmetric 2-naphthol couplings in total synthesis. The types of chirality, chiral biaryl natural products, prior approaches to chiral biaryl natural products, and other catalytic asymmetric biaryl couplings are outlined. The three main categories of chiral catalysts for 2-naphthol coupling (Cu, V, Fe) are described with discussion of their limitations and advantages. Applications of the copper catalyzed couplings in biomimetic syntheses ar...

  14. Asymmetric total synthesis of vindoline.

    Science.gov (United States)

    Kato, Daisuke; Sasaki, Yoshikazu; Boger, Dale L

    2010-03-24

    A concise asymmetric total synthesis of (-)-vindoline (1) is detailed based on a tandem intramolecular [4+2]/[3+2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which the tether linking the initiating dienophile and oxadiazole bears a chiral substituent that controls the facial selectivity of the initiating Diels-Alder reaction and sets absolute stereochemistry of the remaining six stereocenters in the cascade cycloadduct. This key reaction introduces three rings and four C-C bonds central to the pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. Implementation of the approach also required the development of a unique ring expansion reaction to provide a six-membered ring suitably functionalized for introduction of the Delta (6, 7)-double bond found in the core structure of vindoline and defined our use of a protected hydroxymethyl group as the substituent used to control the stereochemical course of the cycloaddition cascade.

  15. Stereoselective Total Synthesis of (-)-Renieramycin T.

    Science.gov (United States)

    Yokoya, Masashi; Toyoshima, Ryoko; Suzuki, Toshihiro; Le, Vy H; Williams, Robert M; Saito, Naoki

    2016-05-20

    A stereoselective total synthesis of (-)-Renieramycin T (1t) from a key tetrahydroisoquinoline intermediate previously utilized in our formal total synthesis of Ecteinascidin 743 is described. The synthesis features a concise approach for construction of the pentacyclic framework using a Pictet-Spengler cyclization of bromo-substituted carbinolamine 17, which obviates the regioselectivity problem of the Pictet-Spengler cyclization. The results of cytotoxicity studies are also presented. PMID:27019081

  16. Total synthesis of solanoeclepin A

    Science.gov (United States)

    Tanino, Keiji; Takahashi, Motomasa; Tomata, Yoshihide; Tokura, Hiroshi; Uehara, Taketo; Narabu, Takashi; Miyashita, Masaaki

    2011-06-01

    Cyst nematodes are troublesome parasites that live on, and destroy, a range of important host vegetable plants. Damage caused by the potato cyst nematode has now been reported in over 50 countries. One approach to eliminating the problem is to stimulate early hatching of the nematodes, but key hatching stimuli are not naturally available in sufficient quantities to do so. Here, we report the first chemical synthesis of solanoeclepin A, the key hatch-stimulating substance for potato cyst nematode. The crucial steps in our synthesis are an intramolecular cyclization reaction for construction of the highly strained tricyclo[5.2.1.01,6]decane skeleton (DEF ring system) and an intramolecular Diels-Alder reaction of a furan derivative for the synthesis of the ABC carbon framework. The present synthesis has the potential to contribute to addressing one of the critical food issues of the twenty-first century.

  17. Biomimetic approach for the synthesis of N, N'-diarylsubstituted formamidines catalyzed by β-cyclodextrin in water

    Institute of Scientific and Technical Information of China (English)

    Dipak R.Patil; Dipak S.Dalal

    2012-01-01

    An environmentally benign and highly efficient biomimetic approach for the synthesis of N,N'-diarylsubstituted formamidines in water catalyzed β-cyclodextrin is described under neutral condition with quantitative yields of products.β-Cyclodextrin has been recovered and reused.

  18. Synthesis and Performance of a Biomimetic Indicator for Alkylating Agents.

    Science.gov (United States)

    Provencher, Philip A; Love, Jennifer A

    2015-10-01

    4-(4-Nitrobenzyl)pyridine (NBP) is a colorimetric indicator compound for many types of carcinogenic alkylating agents. Because of the similar reactivity of NBP and guanine in DNA, NBP serves as a DNA model. NBP assays are used in the toxicological screening of pharmaceutical compounds, detection of chemical warfare agents, environmental hygiene technology, preliminary toxicology tests, mutagenicity of medicinal compounds, and other chemical analyses. Nevertheless, the use of NBP as a DNA model suffers from the compound's low water solubility, its lack of reactive oxygen sites, and dissimilar steric encumbrance compared to DNA. We report herein the design and synthesis of NBP derivatives that address some of these issues. These derivatives have been tested in solution and found to be superior in the colorimetric assay of the alkylating anticancer drug cyclophosphamide. The derivatives have also been integrated into a polymeric silica material which changes color upon the exposure to dangerous alkylating agents, such as iodomethane vapor, without the need for an exogenous base. This material modernizes the NBP assay from a time-consuming laboratory analysis to a real-time solid state sensor, which requires neither solvent nor additional reagents and can detect both gas- and solution-phase alkylating agents.

  19. Asymmetric Total Synthesis of (-)-Cladospolide B

    Institute of Scientific and Technical Information of China (English)

    WANG,Wen-Kuan; ZHANG,Ji-Yong; HE,Jin-Mei; TANG,Shi-Bing; WANG,Xiao-Lei; SHE,Xue-Gong; PAN,Xin-Fu

    2008-01-01

    An enantioselective total synthesis of (-)-cladospolide B was described.The key steps in this synthesis include (a) a Sharpless asymmetric dihydroxylation to elaborate syn diol at C-4 and C-5 positions;(b) a Mitsunobu esterification to reverse the configuration at C-11 from (S) to (R);and (c) a ring-closing metathesis to access the 12-membered macrocyclic ring.

  20. A modified total synthesis of cystothiazole A

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    A modified total synthesis of cystothiazole A is described. In this synthetic strategy, a one-step transformation of acylated oxazolidinone to β-ketoester has been successfully applied, thus making the synthetic route more efficient. This method may also be potentially applied in synthesis of other related β-substituted-β-methoxyl acrylates (bb-MOAs).

  1. Total Synthesis of (±)-Celaphanol A

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    The first total synthesis of (±)-Celaphanol A was accomplished starting from α-cyclocitral and 3,4-dimethoxy benzyl chloride via a six-step process, in which the intramolecular cyclization of ketone 4 with BF3@Et2O afforded an all-cis isomer intermediate for synthesis of aromatic tricyclic diterpenes.

  2. Biomimetic synthesis of highly biocompatible gold nanoparticles with amino acid-dithiocarbamate as a precursor for SERS imaging

    Science.gov (United States)

    Li, Li; Liu, Jianbo; Yang, Xiaohai; Huang, Jin; He, Dinggeng; Guo, Xi; Wan, Lan; He, Xiaoxiao; Wang, Kemin

    2016-03-01

    Amino acid-dithiocarbamate (amino acid-DTC) was developed as both the reductant and ligand stabilizer for biomimetic synthesis of gold nanoparticles (AuNPs), which served as an excellent surface-enhanced Raman scattering (SERS) contrast nanoprobe for cell imaging. Glycine (Gly), glutamic acid (Glu), and histidine (His) with different isoelectric points were chosen as representative amino acid candidates to synthesize corresponding amino acid-DTC compounds through mixing with carbon disulfide (CS2), respectively. The pyrogenic decomposition of amino acid-DTC initiated the reduction synthesis of AuNPs, and the strong coordinating dithiocarbamate group of amino acid-DTC served as a stabilizer that grafted onto the surface of the AuNPs, which rendered the as-prepared nanoparticles a negative surface charge and high colloidal stability. MTT cell viability assay demonstrated that the biomimetic AuNPs possessed neglectful toxicity to the human hepatoma cell, which guaranteed them good biocompatibility for biomedical application. Meanwhile, the biomimetic AuNPs showed a strong SERS effect with an enhancement factor of 9.8 × 105 for the sensing of Rhodamine 6G, and two distinct Raman peaks located at 1363 and 1509 cm-1 could be clearly observed in the cell-imaging experiments. Therefore, biomimetic AuNPs can be explored as an excellent SERS contrast nanoprobe for biomedical imaging, and the amino acid-DTC mediated synthesis of the AuNPs has a great potential in bio-engineering and biomedical imaging applications.

  3. Synthesis and Characterization of a Chondroitin Sulfate Based Hybrid Bio/Synthetic Biomimetic Aggrecan Macromolecule

    Science.gov (United States)

    Sarkar, Sumona

    Lower back pain resulting from intervertebral disc degeneration is one of the leading musculoskeletal disorders confronting our health system. In order to mechanically stabilize the disc early in the degenerative cascade and prevent the need for spinal fusion surgeries, we have proposed the development of a hybrid-bio/synthetic biomimetic proteoglycan macromolecule for injection into the disc in the early stages of degeneration. The goal of this thesis was to incorporate natural chondroitin sulfate (CS) chains into bottle brush polymer synthesis strategies for the fabrication of CS-macromolecules which mimic the proteoglycan structure and function while resisting enzymatic degradation. Both the "grafting-to" and "grafting-through" techniques of bottle brush synthesis were explored. CS was immobilized via a terminal primary amine onto a model polymeric backbone (polyacrylic acid) for investigation of the "grafting-to" strategy and an epoxy-amine step-growth polymerization technique was utilized for the "grafting-through" synthesis of CS-macromolecules with polyethylene glycol backbone segments. Incorporation of a synthetic polymeric backbone at the terminal amine of CS was confirmed via biochemical assays, 1H-NMR and FTIR spectroscopy, and CS-macromolecule size was demonstrated to be higher than that of natural CS via gel permeation chromatography, transmission electron microscopy and viscosity measurements. Further analysis of CS-macromolecule functionality indicated maintenance of natural CS properties such as high fixed charge density, high osmotic potential and low cytotoxicity with nucleus pulposus cells. These studies are the first attempt at the incorporation of natural CS into biomimetic bottle brush structures. CS-macromolecules synthesized via the methods developed in these studies may be utilized in the treatment and prevention of debilitating back pain as well as act as mimetics for other proteoglycans implicated in cartilage, heart valve, and nervous

  4. Total Synthesis of (±)-Hibiscone C

    OpenAIRE

    Ungureanu, Sinziana; Meadows, Maggie; Smith, Joel; Duff, David B.; Burgess, James M.; Goess, Brian C.

    2011-01-01

    A total synthesis of (±)- hibiscone C, one member of the furanosteroid family of natural products that also includes viridin and wortmannin, is reported. Two new pathways for formation of the key diacyl furan subunit are described.

  5. The First Total Synthesis of Isoliquiritin

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A first total synthesis of isoliquiritin was accomplished starting from p-hydroxy- benzaldehyde and 2,4-dihydroxyacetylphenone. The key step is condensation reaction. In synthetic process need not protect the hydroxy group of reacting substance.

  6. Methods for improving enzymatic trans-glycosylation for synthesis of human milk oligosaccharide biomimetics.

    Science.gov (United States)

    Zeuner, Birgitte; Jers, Carsten; Mikkelsen, Jørn Dalgaard; Meyer, Anne S

    2014-10-01

    Recently, significant progress has been made within enzymatic synthesis of biomimetic, functional glycans, including, for example, human milk oligosaccharides. These compounds are mainly composed of N-acetylglucosamine, fucose, sialic acid, galactose, and glucose, and their controlled enzymatic synthesis is a novel field of research in advanced food ingredient chemistry, involving the use of rare enzymes, which have until now mainly been studied for their biochemical significance, not for targeted biosynthesis applications. For the enzymatic synthesis of biofunctional glycans reaction parameter optimization to promote "reverse" catalysis with glycosidases is currently preferred over the use of glycosyl transferases. Numerous methods exist for minimizing the undesirable glycosidase-catalyzed hydrolysis and for improving the trans-glycosylation yields. This review provides an overview of the approaches and data available concerning optimization of enzymatic trans-glycosylation for novel synthesis of complex bioactive carbohydrates using sialidases, α-l-fucosidases, and β-galactosidases as examples. The use of an adequately high acceptor/donor ratio, reaction time control, continuous product removal, enzyme recycling, and/or the use of cosolvents may significantly improve trans-glycosylation and biocatalytic productivity of the enzymatic reactions. Protein engineering is also a promising technique for obtaining high trans-glycosylation yields, and proof-of-concept for reversing sialidase activity to trans-sialidase action has been established. However, the protein engineering route currently requires significant research efforts in each case because the structure-function relationship of the enzymes is presently poorly understood.

  7. Process variables in biomimetic synthesis of silver nanoparticles by aqueous extract of Azadirachta indica (Neem) leaves

    Energy Technology Data Exchange (ETDEWEB)

    Tripathy, A. [VIT University, School of Biotechnology, Chemical and Biomedical Engineering (India); Raichur, Ashok M. [Indian Institute of Science, Department of Materials Engineering (India); Chandrasekaran, N.; Prathna, T. C.; Mukherjee, Amitava, E-mail: amit.mookerjea@gmail.co [VIT University, School of Biotechnology, Chemical and Biomedical Engineering (India)

    2010-01-15

    Owing to widespread applications, synthesis and characterization of silver nanoparticles is recently attracting considerable attention. Increasing environmental concerns over chemical synthesis routes have resulted in attempts to develop biomimetic approaches. One of them is synthesis using plant parts, which eliminates the elaborate process of maintaining the microbial culture and often found to be kinetically favourable than other bioprocesses. The present study deals with investigating the effect of process variables like reductant concentrations, reaction pH, mixing ratio of the reactants and interaction time on the morphology and size of silver nanoparticles synthesized using aqueous extract of Azadirachta indica (Neem) leaves. The formation of crystalline silver nanoparticles was confirmed using X-ray diffraction analysis. By means of UV spectroscopy, Scanning and Transmission Electron Microscopy techniques, it was observed that the morphology and size of the nanoparticles were strongly dependent on the process parameters. Within 4 h interaction period, nanoparticles below 20-nm-size with nearly spherical shape were produced. On increasing interaction time (ageing) to 66 days, both aggregation and shape anisotropy (ellipsoidal, polyhedral and capsular) of the particles increased. In alkaline pH range, the stability of cluster distribution increased with a declined tendency for aggregation of the particles. It can be inferred from the study that fine tuning the bioprocess parameters will enhance possibilities of desired nano-product tailor made for particular applications.

  8. Biomimetic, mild chemical synthesis of CdTe-GSH quantum dots with improved biocompatibility.

    Directory of Open Access Journals (Sweden)

    José M Pérez-Donoso

    Full Text Available Multiple applications of nanotechnology, especially those involving highly fluorescent nanoparticles (NPs or quantum dots (QDs have stimulated the research to develop simple, rapid and environmentally friendly protocols for synthesizing NPs exhibiting novel properties and increased biocompatibility. In this study, a simple protocol for the chemical synthesis of glutathione (GSH-capped CdTe QDs (CdTe-GSH resembling conditions found in biological systems is described. Using only CdCl(2, K(2TeO(3 and GSH, highly fluorescent QDs were obtained under pH, temperature, buffer and oxygen conditions that allow microorganisms growth. These CdTe-GSH NPs displayed similar size, chemical composition, absorbance and fluorescence spectra and quantum yields as QDs synthesized using more complicated and expensive methods.CdTe QDs were not freely incorporated into eukaryotic cells thus favoring their biocompatibility and potential applications in biomedicine. In addition, NPs entry was facilitated by lipofectamine, resulting in intracellular fluorescence and a slight increase in cell death by necrosis. Toxicity of the as prepared CdTe QDs was lower than that observed with QDs produced by other chemical methods, probably as consequence of decreased levels of Cd(+2 and higher amounts of GSH. We present here the simplest, fast and economical method for CdTe QDs synthesis described to date. Also, this biomimetic protocol favors NPs biocompatibility and helps to establish the basis for the development of new, "greener" methods to synthesize cadmium-containing QDs.

  9. Total Synthesis of balanol, Part 2

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Kelly, Nicholas; Tedenborg, Lars;

    1997-01-01

    A convergent enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and the corresponding epoxide 4, both of which undergo highly regio- and stereoselective nucleophilic ring-o...

  10. Enantioselective Total Synthesis of Plectosphaeroic Acid B

    OpenAIRE

    Jabri, Salman Y.; Overman, Larry E.

    2013-01-01

    The first total synthesis of a member of the plectosphaeroic acid family of fungal natural products is reported. Key steps include the late-stage formation of the hindered N6–C9″ bond and stereoselective introduction of the two methylthio substituents.

  11. The total synthesis of (-)-cryptocaryol A.

    Science.gov (United States)

    Dias, L C; Kuroishi, P K; de Lucca, E C

    2015-03-28

    A stereoselective total synthesis of (-)-cryptocaryol A (1) is described. Key features of the 17-step route include the use of three boron-mediated aldol reaction-reduction sequences to control all stereocenters and an Ando modification of the Horner-Wadsworth-Emmons olefination that permitted the installation of the Z double bond of the α-pyrone ring. PMID:25695350

  12. The total synthesis of pantocin B.

    Science.gov (United States)

    Sutton, A E; Clardy, J

    2000-02-10

    [reaction: see text] Pantocin B, an unusual antibiotic produced by Erwinia herbicola, effectively controls E. amylovora, the pathogen causing the plant disease fire blight. A total synthesis of pantocin B from L-alanine, glycine, and L-malic acid is reported. PMID:10814312

  13. Total synthesis of insect antifeedant drimane sesquiterpenes.

    NARCIS (Netherlands)

    Jansen, B.J.M.

    1993-01-01

    The investigations described in this thesis deal with the total synthesis of sesquiterpenes of the drimane family, named for their widespread occurrence in the stem bark of South American Drimys species. These compounds contain the bicyclofarnesol nucleus 1 , which is invariably oxi

  14. Total synthesis of aeruginosin 98B.

    Science.gov (United States)

    Trost, Barry M; Kaneko, Toshiyuki; Andersen, Neil G; Tappertzhofen, Christoph; Fahr, Bruce

    2012-11-21

    The first total synthesis of aeruginosin 98B was accomplished. The key step is a highly diastereoselective Pd-catalyzed intramolecular asymmetric allylic alkylation reaction of a diastereomeric mixture of allylic carbonates that is enabled by the use of racemic phosphine ligand L1.

  15. Biomimetic synthesis and biocompatibility evaluation of carbonated apatites template-mediated by heparin

    Energy Technology Data Exchange (ETDEWEB)

    Deng, Yi [Department of Oral and Maxillofacial Surgery, Laboratory of Interdisciplinary Studies, School and Hospital of Stomatology, Peking University, Beijing 100081 (China); Center for Biomedical Materials and Tissue Engineering, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871 (China); Sun, Yuhua [Department of Oral and Maxillofacial Surgery, Laboratory of Interdisciplinary Studies, School and Hospital of Stomatology, Peking University, Beijing 100081 (China); Chen, Xiaofang [Center for Biomedical Materials and Tissue Engineering, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871 (China); Zhu, Peizhi, E-mail: pzzhu@umich.edu [Center for Biomedical Materials and Tissue Engineering, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871 (China); Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055 (United States); Wei, Shicheng, E-mail: sc-wei@pku.edu.cn [Department of Oral and Maxillofacial Surgery, Laboratory of Interdisciplinary Studies, School and Hospital of Stomatology, Peking University, Beijing 100081 (China); Center for Biomedical Materials and Tissue Engineering, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871 (China)

    2013-07-01

    Biomimetic synthesis of carbonated apatites with good biocompatibility is a promising strategy for the broadening application of apatites for bone tissue engineering. Most researchers were interested in collagen or gelatin-based templates for synthesis of apatite minerals. Inspired by recent findings about the important role of polysaccharides in bone biomineralization, here we reported that heparin, a mucopolysaccharide, was used to synthesize carbonated apatites in vitro. The results indicated that the Ca/P ratio, carbon content, crystallinity and morphology of the apatites varied depending on the heparin concentration and the initial pH value. The morphology of apatite changed from flake-shaped to needle-shaped, and the degree of crystallinity decreased with the increasing of heparin concentration. Biocompatibility of the apatites was tested by proliferation and alkaline phosphatase activity of MC3T3-E1 cells. The results suggested that carbonated apatites synthesized in the presence of heparin were more favorable to the proliferation and differentiation of MC3T3-E1 cells compared with traditional method. In summary, the heparin concentration and the initial pH value play a key role in the chemical constitution and morphology, as well as biological properties of apatites. These biocompatible nano-apatite crystals hold great potential to be applied as bioactive materials for bone tissue engineering. - Highlights: • Heparin was used as a template to synthesize needle-shaped nano-apatite. • Changing the pH value and concentration led to different properties of apatite. • Apatite prepared by heparin was more favorable to the osteogenic differentiation. • Possible synthesis mechanism of apatite templated by heparin was described.

  16. Biomimetic synthesis and biocompatibility evaluation of carbonated apatites template-mediated by heparin

    International Nuclear Information System (INIS)

    Biomimetic synthesis of carbonated apatites with good biocompatibility is a promising strategy for the broadening application of apatites for bone tissue engineering. Most researchers were interested in collagen or gelatin-based templates for synthesis of apatite minerals. Inspired by recent findings about the important role of polysaccharides in bone biomineralization, here we reported that heparin, a mucopolysaccharide, was used to synthesize carbonated apatites in vitro. The results indicated that the Ca/P ratio, carbon content, crystallinity and morphology of the apatites varied depending on the heparin concentration and the initial pH value. The morphology of apatite changed from flake-shaped to needle-shaped, and the degree of crystallinity decreased with the increasing of heparin concentration. Biocompatibility of the apatites was tested by proliferation and alkaline phosphatase activity of MC3T3-E1 cells. The results suggested that carbonated apatites synthesized in the presence of heparin were more favorable to the proliferation and differentiation of MC3T3-E1 cells compared with traditional method. In summary, the heparin concentration and the initial pH value play a key role in the chemical constitution and morphology, as well as biological properties of apatites. These biocompatible nano-apatite crystals hold great potential to be applied as bioactive materials for bone tissue engineering. - Highlights: • Heparin was used as a template to synthesize needle-shaped nano-apatite. • Changing the pH value and concentration led to different properties of apatite. • Apatite prepared by heparin was more favorable to the osteogenic differentiation. • Possible synthesis mechanism of apatite templated by heparin was described

  17. First Total Synthesis of Gliomasolide C and Formal Total Synthesis of Sch-725674.

    Science.gov (United States)

    Seetharamsingh, B; Khairnar, Pankaj V; Reddy, D Srinivasa

    2016-01-01

    Syntheses of two 14-membered macrolides Sch-725674 and Gliomasolide C are described here. The first total synthesis of Gliomasolide C, the short synthesis of Sch-725674, and regioselective Wacker oxidation of internal olefin are the highlights of this disclosure. In addition, a key macrocycle with orthogonal functionalities was designed and synthesized on a gram scale for the generation of analogues. PMID:26633579

  18. Nineteen-step total synthesis of (+)-phorbol.

    Science.gov (United States)

    Kawamura, Shuhei; Chu, Hang; Felding, Jakob; Baran, Phil S

    2016-04-01

    Phorbol, the flagship member of the tigliane diterpene family, has been known for over 80 years and has attracted attention from many chemists and biologists owing to its intriguing chemical structure and the medicinal potential of phorbol esters. Access to useful quantities of phorbol and related analogues has relied on isolation from natural sources and semisynthesis. Despite efforts spanning 40 years, chemical synthesis has been unable to compete with these strategies, owing to its complexity and unusual placement of oxygen atoms. Purely synthetic enantiopure phorbol has remained elusive, and biological synthesis has not led to even the simplest members of this terpene family. Recently, the chemical syntheses of eudesmanes, germacrenes, taxanes and ingenanes have all benefited from a strategy inspired by the logic of two-phase terpene biosynthesis in which powerful C-C bond constructions and C-H bond oxidations go hand in hand. Here we implement a two-phase terpene synthesis strategy to achieve enantiospecific total synthesis of (+)-phorbol in only 19 steps from the abundant monoterpene (+)-3-carene. The purpose of this synthesis route is not to displace isolation or semisynthesis as a means of generating the natural product per se, but rather to enable access to analogues containing unique placements of oxygen atoms that are otherwise inaccessible. PMID:27007853

  19. Biomimetic synthesis of cellular SiC based ceramics from plant precursor

    Indian Academy of Sciences (India)

    O P Chakrabarti; H S Maiti; R Majumdar

    2004-10-01

    A novel biomimetic approach in designing and fabricating engineering ceramic materials has gained much interest in recent times. Following this approach, synthesis has been made of dense Si–SiC duplex ceramic composites and highly porous SiC ceramics in the image of the morphological features inherent in the caudex stem of a local monocotyledonous plant. The process route involves making of a carbonaceous biopreform and its subsequent reaction with an infiltrating silicon melt to yield the biomorphic Si–SiC ceramic composites with flexural strength and Young’s modulus of 264 MPa and 247 Gpa, respectively and loss in weight of only ∼ 9% during oxidative heating up to 1200°C in flowing air. The Si–SiC composites were transformed into porous (49 vol.%) SiC ceramics with complete preservation of microcellular anatomy of the parent plant, by depleting residual silicon phase in channel pores through reaction with carbon. SiC based materials so derived can be used in structural applications and in designing high temperature filters and catalyst supports.

  20. Total Synthesis of (±)-Integrifolin.

    Science.gov (United States)

    Shimomaki, Katsuya; Kusama, Hiroyuki; Iwasawa, Nobuharu

    2016-07-11

    The total synthesis of (±)-integrifolin has been achieved for the first time through the stereoselective preparation of the bicyclo[5.3.0]decane skeleton based on the tungsten-catalyzed cyclization of acyclic trienynes under photoirradiation conditions. Further key transformations of the cyclized product are the Tamao oxidation through cyclic silyl ether, the introduction of two oxygen functionalities by the oxidation of the diene and the construction of three exo-methylene moieties. PMID:27147582

  1. Total synthesis of the indolizidine alkaloid tashiromine

    Directory of Open Access Journals (Sweden)

    McElhinney Alison D

    2008-01-01

    Full Text Available Abstract Background Tashiromine 1 is a naturally occurring indolizidine alkaloid. It has been the subject of thirteen successful total syntheses to date. Our own approach centres on the stereoselective construction of the indolizidine core by capture of an electrophilic acyliminium species by a pendant allylsilane. The key cyclisation precursor is constructed using olefin cross-metathesis chemistry, which has the potential to facilitate both racemic and asymmetric approaches, depending upon the choice of the allylsilane metathesis partner. Results The use of the allyltrimethylsilane cross-metathesis approach enables the rapid construction of the key cyclisation precursor 3 (3 steps from commercial materials, which undergoes acid-induced cyclisation to give the desired bicyclic indolizidine skeleton as a 96:4 mixture of diastereomers. Simple functional group interconversions allowed the completion of the total synthesis of racemic tashiromine in six steps (19% overall yield. Three chiral α-alkoxyallylsilanes (12,14 and 15 were prepared in enantioenriched form and their cross-metathesis reactions studied as part of a putative asymmetric approach to tashiromine. In the event, α-hydroxysilane 12 underwent isomerisation under the reaction conditions to acylsilane 17, while silanes 14 and 15 were unreactive towards metathesis. Conclusion A concise, stereoselective total synthesis of racemic tashiromine has been developed. Attempts to translate this into an asymmetric synthesis have thus far been unsuccessful.

  2. Total synthesis and biological investigation of (-)-promysalin.

    Science.gov (United States)

    Steele, Andrew D; Knouse, Kyle W; Keohane, Colleen E; Wuest, William M

    2015-06-17

    Compounds that specifically target pathogenic bacteria are greatly needed, and identifying the method by which they act would provide new avenues of treatment. Herein we report the concise, high-yielding total synthesis (eight steps, 35% yield) of promysalin, a natural product that displays antivirulence phenotypes against pathogenic bacteria. Guided by bioinformatics, four diastereomers were synthesized, and the relative and absolute stereochemistries were confirmed by spectral and biological analysis. Finally, we show for the first time that promysalin displays two antivirulence phenotypes: the dispersion of mature biofilms and the inhibition of pyoverdine production, hinting at a unique pathogenic-specific mechanism of action.

  3. Total synthesis of insect antifeedant drimane sesquiterpenes.

    OpenAIRE

    Jansen, B.J.M.

    1993-01-01

    The investigations described in this thesis deal with the total synthesis of sesquiterpenes of the drimane family, named for their widespread occurrence in the stem bark of South American Drimys species. These compounds contain the bicyclofarnesol nucleus 1 , which is invariably oxidized at C-11 and/or C-12 and often at other sites as well (see figure 8.1).A few rearranged drimanes, e.g., (+)-colorata-4(13),8-dienolide 6 , and (-)-muzigadial 7 , are also isolated from natural products. The re...

  4. Enantioselective Total Synthesis of (-)-Alstoscholarisine A.

    Science.gov (United States)

    Liang, Xiao; Jiang, Shi-Zhi; Wei, Kun; Yang, Yu-Rong

    2016-03-01

    We report a concise and highly enantioselective total synthesis of (-)-alstoscholarisine A (1), a recently isolated monoterpenoid indole alkaloid that has significant bioactivity in promoting adult neuronal stem cells proliferation. A highly enantioselective (99% ee), intramolecular Ir-catalyzed Friedel-Crafts alkylation of indole 9 with a secondary allylic alcohol was utilized to establish the first stereogenic center upon which the other three contiguous chiral centers were readily set by a highly stereoselective tandem 1,4-addition and aldol reaction. The key tetrahydropyran was constructed through a hemiacetal reduction, and the final aminal bridge was forged by a one-pot reductive amination/cyclization. The conciseness of this approach was highlighted by building core bonds in each step with a minimalist protecting group strategy. PMID:26882407

  5. Total synthesis of diterpenoid steenkrotin A.

    Science.gov (United States)

    Pan, Saiyong; Xuan, Jun; Gao, Beiling; Zhu, An; Ding, Hanfeng

    2015-06-01

    A concise and diastereoselective total synthesis of the diterpenoid (±)-steenkrotin A is described for the first time. The strategy mainly features three key ring formations: 1) a rhodium-catalyzed O-H bond insertion followed by an intramolecular carbonyl-ene reaction to build up the tetrahydrofuran subunit; 2) sequential SmI2 -mediated Ueno-Stork and ketyl-olefin cyclizations to construct the [5,7] spirobicyclic skeleton; and 3) an intramolecular aldol condensation/vinylogous retro-aldol/aldol sequence to form the final six-membered ring with inversion of the relative configuration at the C7 position. PMID:25891977

  6. The Total Synthesis of Inostamycin A.

    Science.gov (United States)

    Yu, Guangri; Jung, Byunghyuck; Lee, Hee-Seung; Kang, Sung Ho

    2016-02-12

    The first total synthesis of inostamycin A is described. With efficient and stereoselective synthetic routes to aldehyde 3 and ketone 4 developed through asymmetric aldol reactions, addition reactions and reduction, and with chiral building blocks, the two large fragments were coupled with remarkable anti stereoselectivity and efficiency by aldol condensation. The coupling reaction provided the complete carbon skeleton with all the requisite functional groups and stereogenic centers for inostamycin A. The two quaternary carbons at C20 and C16 of ketone 4 were elaborated in a highly stereocontrolled manner by addition reactions of the transmetallated 5 to ethyl ketone 6 and the transmetallated 7 to methyl ketone 8, respectively, in which the use of LaCl3 for transmetallation was critical for high coupling efficiency. PMID:26800259

  7. Biomimetic synthesis and antiproliferative properties of racemic natural(-) and unnnatural(+) glyceollin I

    Science.gov (United States)

    A 14-step biomimetic synthetic route to glyceollin I in ca. 1.5% overall yield has been developed. In addition to being useful for the elaboration of analogs that can contribute to SAR, this route provides practical access to analytical standards that may be used for quality control purposes when gl...

  8. Total Synthesis of a Diacetonide Derivative of Thuggacin A.

    Science.gov (United States)

    Yadav, Jhillu S; Dutta, Palash

    2016-03-01

    A highly stereoselective total synthesis of the diacetonide derivative of the antibiotic thuggacin A has been described. The synthesis features the stereoselective Stille cross-coupling reaction to set up the whole carbon framework, aldol condensation to construct the highly substituted conjugated diene, non-Evans syn aldol, CBS reduction, Hantzsch's thiazole synthesis, Horner-Wadsworth-Emmons reaction, and Shiina's macrolactonization. PMID:26856208

  9. Total Synthesis of the Cyanolide A Aglycon

    OpenAIRE

    Gesinski, Michael R.; Rychnovsky, Scott D.

    2011-01-01

    The synthesis of the potent molluscicide, cyanolide A, has been achieved in 10 steps without the use of protecting groups. The synthesis features a key Sakurai macrocyclization/dimerization reaction that simultaneously forms both tetrahydropyran rings and the macrocycle of the natural product.

  10. The total synthesis of cannabisin G

    Directory of Open Access Journals (Sweden)

    YAMU XIA

    2010-12-01

    Full Text Available A convenient method for the synthesis of lignanamide cannabisin G, starting from vanillin, was developed. The convergent synthesis was based on the Stobbe reaction as C–C bond-forming steps to give the skeleton of lignan, which was condensed with a derivative of tyramine to obtain synthetic cannabisin G for the first time.

  11. In situ biomimetic synthesis, characterization and in vitro investigation of bone-like nanohydroxyapatite in starch matrix

    International Nuclear Information System (INIS)

    In this work, we report the synthesis of bone-like hydroxyapatite (HAp) nanorods in wheat starch matrix via a biomimetic process. Characterization of the samples was performed by X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR). Scanning and transmission electron microscopy (SEM and TEM) were used to determine the size, shape and morphology of nano-HAp. The results indicate that, the shape and morphology of nHAp is influenced by the presence of starch as a template agent and rod-like nHAp similar to the inorganic component in the human body is obtained at room temperature. In vitro bioactivity of the synthesized HAp nanocomposites was finally verified by comparison of the HAp's structures and morphology before and after immersion in simulated body fluid (SBF) solution for 3, 7, and 14 days.

  12. Synthesis of Biomimetic Superhydrophobic Surface through Electrochemical Deposition on Porous Alumina

    Institute of Scientific and Technical Information of China (English)

    Jiadao Wang; Ang Li; Haosheng Chen; Darong Chen

    2011-01-01

    The superhydrophobicity of plant leaves is a benefit of the hierarchical structures of their surfaces. These structures have been imitated in the creation of synthetic surfaces. In this paper, a novel process for fabrication of biomimetic hierarchical structures by electrochemical deposition of a metal on porous alumina is described. An aluminum specimen was anodically oxidized to obtain a porous alumina template, which was used as an electrode to fabricate a surface with micro structures through electrochemical deposition of a metal such as nickel and copper after the enlargement of pores. Astonishingly, a hierarchical structure with nanometer pillars and micrometer clusters was synthesized in the pores of the template. The nanometer pillars were determined by the nanometer pores. The formation of micrometer clusters was related to the thin walls of the pores and the crystallization of the metal on a flat surface. From the as-prepared biomimetic surfaces, lotus-leaf-like superhydrophobic surfaces with nickel and copper deposition were achieved.

  13. Development and application of biomimetic electrospun nanofibers in total joint replacement

    Science.gov (United States)

    Song, Wei

    Failure of osseointegration (direct anchorage of an implant by bone formation at the bone-implant surface) and implant infection (such as that caused by Staphylococcus aureus, S. aureus) are the two main causes of implant failure and loosening. There is a critical need for orthopedic implants that promote rapid osseointegration and prevent bacterial colonization, particularly when placed in bone compromised by disease or physiology of the patients. A better understanding of the key factors that influence cell fate decisions at the bone-implant interface is required. Our study is to develop a class of "bone-like" nanofibers (NFs) that promote osseointegration while preventing bacterial colonization and subsequent infections. This research goal is supported by our preliminary data on the preparation of coaxial electrospun NFs composed of polycaprolactone (PCL) and polyvinyl alcohol (PVA) polymers arranged in a core-sheath shape. The PCL/PVA NFs are biocompatible and biodegradable with appropriate fiber diameter, pore size and mechanical strength, leading to enhanced cell adhesion, proliferation and differentiation of osteoblast precursor cells. The objective is to develop functionalized "bone-like" PCL/PVA NFs matrix embedded with antibiotics (doxycycline (Doxy), bactericidal and anti-osteoclastic) on prosthesis surface. Through a rat tibia implantation model, the Doxy incorporated coaxial NFs has demonstrated excellent in promoting osseointegration and bacteria inhibitory efficacy. NFs coatings significantly enhanced the bonding between implant and bone remodeling within 8 weeks. The SA-induced osteomyelitis was prevented by the sustained release of Doxy from NFs. The capability of embedding numerous bio-components including proteins, growth factors, drugs, etc. enables NFs an effective solution to overcome the current challenged issue in Total joint replacement. In summary, we proposed PCL/PVA electrospun nanofibers as promising biomaterials that can be applied on

  14. Synthesis of the Biomimetic Polymer: Aliphatic Diamine and RGDS Modified Poly(d,l-lactic acid)

    Institute of Scientific and Technical Information of China (English)

    Xu Feng NIU; Yuan Liang WANG; Yan Feng LUO; Jun PAN; Juan Fang SHANG; Li Xia GUO

    2005-01-01

    A novel poly(d,l-lactic acid) (PDLLA) based biomimetic polymer was synthesized by grafting maleic anhydride, butanediamine and arg-gly-asp-ser (RGDS) peptides onto the backbone of PDLLA, aiming to overcome the acidity and auto-accelerating degradation of PDLLA during degradation and to improve its biospecificity and biocompatibility. The synthetic copolymer was characterized by FTIR, 13C NMR and amino acid analyzer (AAA).

  15. Biomimetic synthesis of hybrid nanocomposite scaffolds by freeze-thawing and freeze-drying

    Indian Academy of Sciences (India)

    S Nayar; A K Pramanick; A Guha; B K Mahato; M Gunjan; A Sinha

    2008-06-01

    The aim of this study is to biomimetically synthesize hydroxyapatite–hydrophilic polymer scaffolds for biomedical applications. This organic–inorganic hybrid has been structurally characterized and reveals a good microstructural control as seen by the SEM analysis and the nanosize of the particulates is confirmed by AFM microscopy. The characterization of such nano-structured composites would allow researchers to design new systems, tailoring properties for different applications.

  16. Synthesis of biomimetic cerium oxide by bean sprouts bio-template and its photocatalytic performance

    Institute of Scientific and Technical Information of China (English)

    周梦凯; 张凯; 陈丰; 陈志刚

    2016-01-01

    Biomimetic nano CeO2 materials were prepared by using bean sprouts as bio-template through impregnation and thermal decomposition. For characterization of structure, X-ray diffraction spectroscopy (XRD), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), UV-Vis diffuse reflectance spectra (UV-Vis/DRS) nitrogen adsorp-tion-desorption measurements and Labsolar H2 system were adopted. The results demonstrated that the samples prepared at 550 ºC not only completely removed the original bio-template, but also retained the morphology and microstructure of bean sprouts. Then the biomorphic structure of fluorite structure CeO2 material was obtained. Micro-pores with a diameter of about 2–3 nm were distributed among the particles, which provided more favorable channel for the photocatalytic reaction. Biomimetic CeO2 materials exhibited clear red shift (50 nm) compared with powder CeO2, which could be excited by visible irradiation. Biomimetic CeO2 materials dis-played the superior photocatalytic activity for the hydrogen production by water splitting under the sunlight irradiation, the hydrogen yield could reach 400μmol/g catalyst after 6 h.

  17. Total synthesis of (±)-divanillyltetrahydrofuran ferulate

    Indian Academy of Sciences (India)

    Ya-Mu Xia; Jia You; Qi Wang

    2010-05-01

    A convenient method for the synthesis of sesquilignan threo- and erythro-(±)-divanillyltetrahydrofuran ferulate is described. The synthesis was based on a unified synthetic strategy involving two Stobbe condensations to give the skeleton of lignan, and then reduction reaction to form meso- and threo-(±)-secoisolanciresinol. meso- and threo-(±)-secoisolanciresinol were separated by flash column chromatography, followed by intramolecular reaction with TsCl to afford the key intermediate meso- or threo-(±)-shonanin, then condensation with ferulaic acid to obtain sesquilignan threo- or its analogue erythro-(±)-divanillyltetrahydrofuran ferulate.

  18. The application of the organic matrix to the biomimetic materials synthesis%有机基质在仿生材料合成中的应用

    Institute of Scientific and Technical Information of China (English)

    杨林; 郭玉明; 王键吉

    2000-01-01

      利用有机基质的模板作用通过仿生合成可以制备出性能优异的无机材料。文章综述了两亲有机分子、有机高分子、生物大分子三种有机基质在仿生材料合成中的应用,并对仿生材料合成这一新兴研究领域的发展趋势及广阔前景作了进一步的展望。%  Using the templating of the organic matrix, the inorganic materials with excellent properties can be perpared by the biomimetic synthesis. Application of three types of organic matrices(amphiphilic molecules, organic polymers and biological macromolecules) to the biomimetic materials synthesis is reviewed in this paper. The developing trend and broad prospects of the biomimetic materials synthesis is also discussed.

  19. Total Synthesis of the Antitumor Antibiotic Basidalin.

    Science.gov (United States)

    Acosta, Jaime A M; Muddala, Ramesh; Barbosa, Luiz C A; Boukouvalas, John

    2016-08-01

    The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal. PMID:27347696

  20. The Total Synthesis of 14-Deoxycrassin and Pseudoplexaurol: A Convergent Synthesis of Cyclization Precursor

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    The synthesis of epoxy aldehyde 4, a cyclization precursor for the total synthesis of 14-deoxycrassin and pseudoplexaurol, starting from geraniol in a convergent and stereoselective manner, is described.

  1. Total Synthesis of Mycalolides A and B through Olefin Metathesis.

    Science.gov (United States)

    Kita, Masaki; Oka, Hirotaka; Usui, Akihiro; Ishitsuka, Tomoya; Mogi, Yuzo; Watanabe, Hidekazu; Tsunoda, Masaki; Kigoshi, Hideo

    2015-11-16

    An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1-C19 trisoxazole and C20-C35 side-chain segments through the use of olefin metathesis and esterification as well as Julia-Kocienski olefination and enamide formation as key steps. PMID:26450520

  2. First total synthesis of (+/-)-3-hydroxy-11-norcytisine

    DEFF Research Database (Denmark)

    Yohannes, Daniel; Hansen, Camilla Petrycer; Akireddy, Srinivasa Rao;

    2008-01-01

    The first total synthesis of the natural product 3-hydroxy-11-norcytisine ( 1), structurally related to cytisine ( 2), a benchmark ligand at neuronal nicotinic acetylcholine receptors (NNRs), has been achieved. The synthesis permits the unambiguous confirmation of the structure originally proposed...

  3. Total Synthesis of Mycalolides A and B through Olefin Metathesis.

    Science.gov (United States)

    Kita, Masaki; Oka, Hirotaka; Usui, Akihiro; Ishitsuka, Tomoya; Mogi, Yuzo; Watanabe, Hidekazu; Tsunoda, Masaki; Kigoshi, Hideo

    2015-11-16

    An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1-C19 trisoxazole and C20-C35 side-chain segments through the use of olefin metathesis and esterification as well as Julia-Kocienski olefination and enamide formation as key steps.

  4. Total synthesis of the potent microtubule-stabilizing agent (+)-discodermolide.

    Science.gov (United States)

    Harried, Scott S; Lee, Christopher P; Yang, Ge; Lee, Tony I H; Myles, David C

    2003-08-22

    The total synthesis of the potent microtubule-stabilizing, antimitotic agent (+)-discodermolide is described. The convergent synthetic strategy takes advantage of the diastereoselective alkylation of a ketone enolate to establish the key C15-C16 bond. The synthesis is amenable to preparation of gram-scale quantities of (+)-discodermolide and analogues.

  5. Study Toward the Total Synthesis of Pyrenophorin

    Directory of Open Access Journals (Sweden)

    Everaldo F. Santos Filho

    2012-06-01

    Full Text Available Macrodiolides are macrocyclic compounds containing two ester groups in a cyclic chain. Of this class of compounds, Pyrenophorin (1 shows antifungal activity, and is produced from the pathogenic fungus Pyrenophora avenae. As this substance, derived from nature, is isolated in small quantities, an asymmetric synthesis using a simple and efficient methodology would be of great interest. The proposed synthetic route starts with the protection of propargyl alcohol 3 using DHP and feldspar as catalyst. Compound 5 obtained in this reaction was then subjected to acid-base reaction between the acetylenic proton and 1 eq. n-BuLi, leading to formation of the acetylide 5A. The 1,2- addition reaction between 5A and g-valerolactone (6 leads to the formation of alkinone 7 in 67% yield. Subsequently, compound 7 was subjected to a ketalization reaction using the same feldspar catalyst. Ketal 8 was formed under concomitant removal of the THP group. The product of this reaction (8 was then submitted to a reduction reaction of the triple bond to form olefin 9 with E configuration. Currently, the conditions for obtaining 10 by oxidation using Jones reagent, are being optimized. Compound 10,    obtained as described, is being subjected to a macrolactonization reaction. Various conditions including the use of enzymes are being studied. In addition, a study involving the enantioselective synthesis of (R,R-(--pyrenophorin, using enzymatic kinetic resolution of the racemic mixture of compound 8, is in progress in the group

  6. Biomimetic synthesis of modified calcium phosphate fine powders and their in vitro studies

    Energy Technology Data Exchange (ETDEWEB)

    Gergulova, R., E-mail: rumigg@yahoo.com; Tepavitcharova, S., E-mail: rumigg@yahoo.com; Rabadjieva, D., E-mail: rumigg@yahoo.com; Sezanova, K., E-mail: rumigg@yahoo.com; Ilieva, R., E-mail: rumigg@yahoo.com [Institute of General and Inorganic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 11, 1113 Sofia (Bulgaria); Alexandrova, R.; Andonova-Lilova, B. [Institute of Experimental Morphology, Pathology and Anthropology with Museum, BAS, Acad. G. Bonchev Str., Bl. 25, Sofia (Bulgaria)

    2013-12-16

    Biomimetic approach and subsequent high-temperature treatment were used to synthesize ion modified calcium phosphate fine powders. Thus, using Simulated Body Fluid (SBF) as an ion modifier, a bi-phase mixture of ion modified β-tricalcium phosphate and hydroxyapatite (β-TCP + HA) was prepared. The use of SBF electrolyte solution enriched with Mg{sup 2+} or Zn{sup 2+} yielded monophase β-tricalcium phosphate additionally modified with Mg{sup 2+} or Zn{sup 2+} (Mg-β-TCP or Zn-β-TCP). The in vitro behavior of the prepared powders on cell viability and proliferation of murine BALB/c 3T3 fibroblasts and of human Lep 3 cells was studied by MTT test assays and Mosmann method after 72 h incubation. The relative cell viability was calculated.

  7. Total synthesis: Towards artificial terpene cyclases

    Science.gov (United States)

    Willot, Matthieu; Christmann, Mathias

    2010-07-01

    The plant-derived sesquiterpene englerin A is a potent inhibitor of several renal cancer cell lines. Two recent total syntheses have utilized cationic gold(I)-complexes to coax readily available open-chain precursors into englerin's challenging oxotricyclic core with enzyme-like precision.

  8. Biomimetic Synthesis of Oiigostilbenes%二苯乙烯类低聚物的仿生合成

    Institute of Scientific and Technical Information of China (English)

    李文玲; 臧鹏; 李洪福; 杨世霞

    2012-01-01

    天然二苯乙烯低聚物是一类自然界分布广泛的多酚化合物,因其结构复杂且生物活性多样而受到密切关注,但此类化合物天然资源的稀少极大限制了其构效关系的调查及活性药物的筛选。近年来许多化学家对此类低聚物的仿生合成方法做了广泛而深入的研究,已形成一个新的研究热点。本文详尽综述了迄今三十多年来二苯乙烯类低聚物的仿生合成研究进展,包括在不同介质中的酶催化或金属氧化剂催化的氧化偶联方法、光催化的异构化及强酸催化下的环合反应,由不同的二苯乙烯前体通过仿生合成途径,构建出结构多样的二苯乙烯低聚物。此外,本文对该类低聚物的仿生合成研究前景做了展望。%Natural oligostilbenes are a class of plant polyphenols widely distributed in nature, and have received considerable attention in the chemical and biological fields because of their structural complexity as well as their diverse bioactivities. These oligomers and their derivatives are potentially useful leading compounds for drug development. Further investigations of structure-activity of oligostilbenes to screen active drugs were limited for their scarce availability in natural raw materials. Biosynthetic strategies towards these oligomers are studied widely and intensively by a number of chemists in recent years and has been a hot research topic. In this paper, the progress in the studies on the biomimetic synthesis of oligostilbenes over the past thirty years is reviewed in detail, including oxidative coupling reactions catalyzed by enzymes or metallic oxidants in various reaction mediums, isomerization under UV irradiation and cyclization induced by several strong acids. Diverse complex molecular architectures of oligostilbenes are thus constructed from a wide array of stilbene precursors through biomimetic routes. The future synthetic trend of oligostilbenes is also prospected.

  9. First total synthesis of (±)-abyssinoflavanone V

    Institute of Scientific and Technical Information of China (English)

    Jin Hui Yang; Yan Min Zhao; Cong Bin Ji

    2008-01-01

    The total synthesis of (±)-abyssinoflavanone V was first achieved through C-prenylation, selective protection of phenolic hydroxyl group, aldol condensation, cyclization and deprotection starting from cheap 4-hydroxybenzaldehyde and 2,4,6-trihydroxyacetophenone, with total yield 24%. All structures of new compounds were confirmed by IR, 1H NMR and MS.

  10. First total synthesis of (±)-sepicanin A

    Institute of Scientific and Technical Information of China (English)

    Jin Hui Yang; Wen Qian Huang; Jun Shan Luo; Dong Dong Guo; Yu Heng Zhang; Hong Jun Li

    2012-01-01

    A facile approach for the first total synthesis of naturally occurring geranylated flavanoids sepicanin A has been obtained with total yield 16% starting from 2,4,6-trihydroxyacetophenone after four steps.The key step was the protic acids (HCl or p-TsOH)-catalyzed benzopyrone formation in a protic polar solvent by deprotection and cyclization of chalcone in one step.

  11. Total synthesis and stereochemical revision of (+)-aeruginosin 298-A.

    Science.gov (United States)

    Wipf, P; Methot, J L

    2000-12-28

    [structure:see text] Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor. PMID:11150202

  12. Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

    Directory of Open Access Journals (Sweden)

    Hiroaki Miyaoka

    2009-11-01

    Full Text Available Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis.

  13. Biomimetic synthesis of enamel-like hydroxyapatite on self-assembled monolayers

    Energy Technology Data Exchange (ETDEWEB)

    Li Hong [Department of Materials Science and Engineering, Jinan University, Guangzhou, 510632 (China); Huang Weiya [Department of Chemistry, Jinan University, Guangzhou, 510632 (China); Zhang Yuanming [Department of Chemistry, Jinan University, Guangzhou, 510632 (China)]. E-mail: tzhangym@jnu.edu.cn; Zhong Mei [Department of Stomatology, Affiliated Hospital of Jinan University, Guangzhou, 510632 (China)

    2007-05-16

    Hydroxyapatite (HAp) crystals mimicking tooth enamel in chemical composition and morphology were formed on sulfonic-terminated self-assembled monolayer (SAM) in 1.5SBF with F{sup -} at 50 {sup o}C for 7 days. F{sup -} ions showed a marked effect on the composition and morphology of deposited HAp crystals. In the absence of F{sup -} ions, HAp containing CO{sub 3} {sup 2-} were formed on SAM, and worm-like crystals of 200-300 nm in length aggregated to form a spherical morphology. When F{sup -} was added, HAp crystals containing both CO{sub 3} {sup 2-} and F{sup -} were formed on SAM. Needle-shaped crystals of high aspect ratio and 1-2 {mu}m in length grew elongated along the c-axial direction. In addition, these needle-shaped crystals grew in bundles, mimicking HAp crystals in tooth enamel. After the process of ripening, the needles in bundle grew to large size of up to 10 {mu}m in length, and still kept no crystal-crystal fusion like enamel HAp crystals. The formation of enamel-like HAp can be attributed to the substitute of F{sup -} for OH{sup -} by disturbing the normal progress of HAp formation on SAM. The results suggest potential applications in preparing a novel dental material by a simple method. -- Graphical abstract: Hydroxyapatite (HAp) crystals mimicking tooth enamel in chemical composition and morphology were formed on self-assembled monolayer (SAM) by a biomimetic process. The needle-shaped crystals grew in bundles, mimicking HAp crystals in tooth enamel. Display Omitted.

  14. Biomimetic synthesis of enamel-like hydroxyapatite on self-assembled monolayers

    International Nuclear Information System (INIS)

    Hydroxyapatite (HAp) crystals mimicking tooth enamel in chemical composition and morphology were formed on sulfonic-terminated self-assembled monolayer (SAM) in 1.5SBF with F- at 50 oC for 7 days. F- ions showed a marked effect on the composition and morphology of deposited HAp crystals. In the absence of F- ions, HAp containing CO32- were formed on SAM, and worm-like crystals of 200-300 nm in length aggregated to form a spherical morphology. When F- was added, HAp crystals containing both CO32- and F- were formed on SAM. Needle-shaped crystals of high aspect ratio and 1-2 μm in length grew elongated along the c-axial direction. In addition, these needle-shaped crystals grew in bundles, mimicking HAp crystals in tooth enamel. After the process of ripening, the needles in bundle grew to large size of up to 10 μm in length, and still kept no crystal-crystal fusion like enamel HAp crystals. The formation of enamel-like HAp can be attributed to the substitute of F- for OH- by disturbing the normal progress of HAp formation on SAM. The results suggest potential applications in preparing a novel dental material by a simple method. -- Graphical abstract: Hydroxyapatite (HAp) crystals mimicking tooth enamel in chemical composition and morphology were formed on self-assembled monolayer (SAM) by a biomimetic process. The needle-shaped crystals grew in bundles, mimicking HAp crystals in tooth enamel. Display Omitted

  15. Amine-catalyzed direct aldol reactions of hydroxy- and dihydroxyacetone: biomimetic synthesis of carbohydrates.

    Science.gov (United States)

    Popik, Oskar; Pasternak-Suder, Monika; Leśniak, Katarzyna; Jawiczuk, Magdalena; Górecki, Marcin; Frelek, Jadwiga; Mlynarski, Jacek

    2014-06-20

    This article presents comprehensive studies on the application of primary, secondary, and tertiary amines as efficient organocatalysts for the de novo synthesis of ketoses and deoxyketoses. Mimicking the actions of aldolase enzymes, the synthesis of selected carbohydrates was accomplished in aqueous media by using proline- and serine-based organocatalysts. The presented methodology also provides direct access to unnatural L-carbohydrates from the (S)-glyceraldehyde precursor. Determination of the absolute configuration of all obtained sugars was feasible using a methodology consisting of concerted ECD and VCD spectroscopy.

  16. Synthesis and Characterization of Biomimetic High Density Lipoprotein Nanoparticles To Treat Lymphoma

    Science.gov (United States)

    Damiano, Marina Giacoma

    High density lipoproteins (HDLs), natural nanoparticles that function as vehicles for cholesterol transport, have enhanced uptake by several human cancers. This uptake is mediated, in part, by the high affinity HDL receptor, scavenger receptor B-1 (SR-B1). More specifically, studies show that the rate of cellular proliferation of lymphoma, a cancer of the lymphocytes, is directly proportional to the amount of HDL-cholesterol available. Thus, targeting of HDL-cholesterol uptake by these cells could be an effective therapeutic approach that may have lower toxicity to healthy cells compared to conventional therapies. Biomimetic HDL can be synthesized using a gold nanoparticle template (HDL-AuNPs), which provides control over size, shape, and surface chemistry. Like their natural counterparts, HDL-AuNPs sequester cholesterol. However, since the gold nanoparticle replaces the cholesterol core of natural HDL, HDL-AuNPs inherently deliver less cholesterol. We show that HDL-AuNPs are able to induce dose dependent apoptosis in B cell lymphoma cell lines and reduce tumor volume following systemic administration to mice bearing B cell lymphoma tumors. Furthermore, HDL-AuNPs are neither toxic to healthy human lymphocytes (SR-B1-), nor to hepatocytes and macrophages (SR-B1+), which are cells naturally encountered by HDLs. Manipulation of cholesterol flux and targeting of SR-B1 are responsible for the efficacy of HDL-AuNPs against B cell lymphoma. HDL-AuNPs could be used to treat B cell lymphomas and other diseases that involve pathologic accumulation of cholesterol. Titanium dioxide nanoparticle (TiO2 NP) core HDLs (HDL-TiO 2 NPs) have been synthesized for high resolution cellular localization studies and for future use as a therapeutic and imaging agent. In initial studies, HDL-TiO(2 NPs display maximum uptake in B cell lymphoma cell lines. X-ray fluorescence microscopy studies show interaction between HDL-TiO2 NPs and cells 10 minutes after treatment and internalization after

  17. Synthesis of nanogranular Fe3O4/biomimetic hydroxyapatite for potential applications in nanomedicine: structural and magnetic characterization

    Science.gov (United States)

    Del Bianco, L.; Lesci, I. G.; Fracasso, G.; Barucca, G.; Spizzo, F.; Tamisari, M.; Scotti, R.; Ciocca, L.

    2015-06-01

    We realized the synthesis of a novel nanogranular system consisting of magnetite nanoparticles embedded in biomimetic carbonate hydroxyapatite (HA), for prospective uses in bone tissue engineering. An original two-step method was implemented: in the first step, magnetite nanoparticles are prepared by refluxing an aqueous solution of Fe(SO4) and Fe2(SO4)3 in an excess of tetrabutilammonium hydroxide acting as surfactant; then, the magnetite nanoparticles are coated with a Ca(OH)2 layer, to induce the growth of HA directly on their surface, by reaction of Ca(OH)2 with HPO42-. Two nanogranular samples were collected with magnetite content ˜0.8 and ˜4 wt%. The magnetite nanoparticles and the composite material were investigated by x-ray diffraction, Fourier transform infrared spectroscopy and transmission electron microscopy. These analyses provided information on the structure of the nanoparticles (mean size ˜6 nm) and revealed the presence of surface hydroxyl groups, which promoted the subsequent growth of the HA phase, featuring a nanocrystalline lamellar structure. The magnetic study, by a superconducting quantum interference device magnetometer, has shown that both the as-prepared and the HA-coated magnetite nanoparticles are superparamagnetic at T = 300 K, but the magnetization relaxation process is dominated by dipolar magnetic interactions of comparable strength. In the three samples, a collective frozen magnetic regime is established below T ˜ 20 K. These results indicate that the magnetite nanoparticles tend to form agglomerates in the as-prepared state, which are not substantially altered by the HA growth, coherently with the creation of electrostatic hydrogen bonds among the surface hydroxyl groups.

  18. Biomimetic magnetic nanoparticles

    Directory of Open Access Journals (Sweden)

    Michael T. Klem

    2005-09-01

    Full Text Available Magnetic nanoparticles are of considerable interest because of their potential use in high-density memory devices, spintronics, and applications in diagnostic medicine. The conditions for synthesis of these materials are often complicated by their high reaction temperatures, costly reagents, and post-processing requirements. Practical applications of magnetic nanoparticles will require the development of alternate synthetic strategies that can overcome these impediments. Biomimetic approaches to materials chemistry have provided a new avenue for the synthesis and assembly of magnetic nanomaterials that has great potential for overcoming these obstacles.

  19. Total Synthesis of Three New Dihydrostilbenes from Bulbophllum odoratissimum

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    A total synthesis of three new dihydrostilbenes, 1, 2 and 3, which were isolated from Bulbophyllum odoratissimum Lindl. with significant cytotoxicity toward human cancer cell lines,was developed via Horner reaction etc. The natural products 1, 2 and 3 were obtained in 5.8%,6.6% and 5.9%, respectively.

  20. The First Total Synthesis of Triprenylquinone and Hydroquinones

    Institute of Scientific and Technical Information of China (English)

    Chun Hong LI; Xue Song CHEN; Guang Lian ZHOU; Zhi Xiang XIE; Ying LI

    2005-01-01

    First total synthesis of triprenylquinone and hydroquinones, three naturally occurring compound 1, 2 and (±) 3, have been achieved from readily available 2-bromo-5-methyl-1,4-dimethoxybenzene 4 and geranyl bromide. The triprenylquinone and hydroquinones precursor were readily prepared with use of a Julia reaction.

  1. Expedient total synthesis of pyrrothine natural products and analogs

    DEFF Research Database (Denmark)

    Hjelmgaard, Thomas; Givskov, Michael Christian; Nielsen, John

    2007-01-01

    This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride...

  2. Enantioselective Total Synthesis of the (+) Antipode of Zeylenone

    Institute of Scientific and Technical Information of China (English)

    An LIU; Zhan Zhu LIU; Zhong Mei ZOU; Shi Zhi CHEN; Li Zhen XU; Shi Lin YANG

    2004-01-01

    Starting from shikimic acid, the total synthesis of zeylenone was studied. The product was proved to be the (+)antipode of zeylenone through analysis and comparison of their respective spectra (including NMR, MS, IR and CD) and optical data. The absolute configuration of the natural product was thus determined to be (1 S,2S,3R).

  3. The total synthesis of 3b-hydroxynagilactone F

    NARCIS (Netherlands)

    Reuvers, J.T.A.

    1985-01-01

    The investigations described in this thesis deal with the total synthesis of physiologically active nor- and bisnorditerpenoid dilactones (fig.1).The goal was to design a synthetic route for this class of natural products and its derivatives. From a retrosynthe

  4. Biomimetic, Mild Chemical Synthesis of CdTe-GSH Quantum Dots with Improved Biocompatibility

    OpenAIRE

    Pérez-Donoso, José M.; Monrás, Juan P; Denisse Bravo; Adam Aguirre; Quest, Andrew F.; Igor O Osorio-Román; Aroca, Ricardo F.; Chasteen, Thomas G.; Vásquez, Claudio C.

    2012-01-01

    Multiple applications of nanotechnology, especially those involving highly fluorescent nanoparticles (NPs) or quantum dots (QDs) have stimulated the research to develop simple, rapid and environmentally friendly protocols for synthesizing NPs exhibiting novel properties and increased biocompatibility. In this study, a simple protocol for the chemical synthesis of glutathione (GSH)-capped CdTe QDs (CdTe-GSH) resembling conditions found in biological systems is described. Using only CdCl(2), K(...

  5. Biomimetic synthesis of high-t{sub c}, type-II superconductor nanowires

    Energy Technology Data Exchange (ETDEWEB)

    Hall, S.R. [Centre for Organized Matter Chemistry, School of Chemistry, University of Bristol, Cantock' s Close, Bristol BS8 1TS (United Kingdom)

    2006-02-17

    Chitosan from crab shells is used to control the synthesis of superconductors. The morphological control over crystallization provided by the chitosan matrix during calcination allows the production of nanowires of the high-T{sub c} superconductor Y124 (YBa{sub 2}Cu{sub 4}O{sub 8}). SQUID magnetometry of these nanowires indicates that the high T{sub c} is successfully retained in this highly anisotropic and technologically important morphology. (Abstract Copyright [2006], Wiley Periodicals, Inc.)

  6. Asymmetric Total Synthesis of a Diastereisomer A of Tuxpanolide

    Institute of Scientific and Technical Information of China (English)

    WANG,Jin-Xin; ZHANG,Chao-Xin; LI,Ying

    2004-01-01

    @@ α-Alkylidene-β-hydroxy butyrolactones have been attractive and challenging targets for organic synthesis in various laboratories because that not only they are rich in skeletal diversity and stereochemistry complexity but also many of them possess quite intriguing and wide biological activities.[1] A novel class of the phytane-type diterpenoid named Tuxpanolide, bearing α-alkylidene-β-hydroxy-γ-butyrolactone skeleton, was isolated from Perymenium hintonii in Central Mexico by Maldonado and co-wokers in 1998.[2] Now we firstly report the efficient strategy of the stereocontrolled total synthesis of a diastereisomer A of Tuxpanolide.

  7. Concise total synthesis and structural revision of (+)-pestalazine B.

    Science.gov (United States)

    Pérez-Balado, Carlos; de Lera, Angel R

    2010-11-21

    A convergent synthesis of the proposed structure of (+)-pestalazine B has been achieved in 4 steps using the N-alkylation of an unprotected tryptophan diketopiperazine with a 3a-bromopyrrolidinoindoline as the key step. Although its structure was confirmed by X-ray analysis, the spectroscopic data did not match those of the natural product. The versatility of the methodology allowed the preparation of several diastereomers, and the database generated led to the proposal of an isomeric structure for the natural alkaloid where the d-leucine and d-phenylalanine residues exchanged positions, which was corroborated by total synthesis. PMID:20848034

  8. Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon.

    Science.gov (United States)

    Kolleth, Amandine; Gebauer, Julian; ElMarrouni, Abdelatif; Lebeuf, Raphael; Prévost, Céline; Brohan, Eric; Arseniyadis, Stellios; Cossy, Janine

    2016-01-01

    We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure. PMID:27556024

  9. Catalytic Asymmetric Total Synthesis of Hedyosumins A, B, and C.

    Science.gov (United States)

    Sun, Wang-Bin; Wang, Xuan; Sun, Bing-Feng; Zou, Jian-Ping; Lin, Guo-Qiang

    2016-03-18

    The first and asymmetric total synthesis of hedyosumins A, B, and C was accomplished in 13-14 steps from simple starting materials. The essential tools that allow us to access the tetracyclic skeleton include an organocatalytic [4 + 3] cycloaddition reaction, an intramolecular aldol condensation, and an intramolecular carboxymercuration/demercuration enabled lactonization. A CBS-catalyzed asymmetric reduction was employed to boost the ee of the synthetic natural products to an excellent level. This synthesis established the absolute configurations of hedyosumins A, B, and C. PMID:26925758

  10. Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon

    Science.gov (United States)

    Kolleth, Amandine; Gebauer, Julian; ElMarrouni, Abdelatif; Lebeuf, Raphael; Prévost, Céline; Brohan, Eric; Arseniyadis, Stellios; Cossy, Janine

    2016-01-01

    We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure. PMID:27556024

  11. Total Synthesis of Six 3,4-Unsubstituted Coumarins

    Directory of Open Access Journals (Sweden)

    Wenqing Gao

    2013-12-01

    Full Text Available In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins—7-hydroxy-6,8-dimethoxy-coumarin (isofraxidin, 7-hydroxy-6-methoxycoumarin (scopoletin, 6,7,8-trimethoxy-coumarin, 6,7-dimethoxycoumarin (scoparone, and 7,8-dihydroxycoumarin (daphnetin and one synthetic coumarin, 7-hydroxy-6-ethoxycoumarin. Moreover, five important o-hydroxybenzaldehyde intermediates were also obtained, namely 2,4-dihydroxy-3,5-dimethoxybenzaldehyde, 2,4-dihydroxy-5-methoxybenzaldehyde, 5-ethoxy-2,4-dihydroxy-benzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxy-benzaldehyde. The method developed herein involves just three or four steps and allows for the rapid synthesis of these important molecules in excellent yields. This is the first synthesis of 6,7,8-trimethoxycoumarin and 7-hydroxy-6-ethoxycoumarin.

  12. Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.

    Science.gov (United States)

    Yuan, Changxia; Jin, Yehua; Wilde, Nathan C; Baran, Phil S

    2016-07-11

    In the realm of natural product chemistry, few isolates have risen to the level of fame justifiably accorded to Taxol (1) and its chemical siblings. This report describes the most concise route to date for accessing the highly oxidized members of this family. As representative members of taxanes containing five oxygen atoms, decinnamoyltaxinine E (2) and taxabaccatin III (3), have succumbed to enantioselective total synthesis for the first time in only 18 steps from a simple olefin starting material. The strategy holistically mimics nature's approach (two-phase synthesis) and features a carefully choreographed sequence of stereoselective oxidations and a remarkable redox-isomerization to set the key trans-diol present in 2 and 3. This work lays the critical groundwork necessary to access even higher oxidized taxanes such as 1 in a more practical fashion, thus empowering a medicinal chemistry campaign that is not wedded to semi-synthesis. PMID:27240325

  13. Xenicane Natural Products: Biological Activity and Total Synthesis.

    Science.gov (United States)

    Betschart, Leo; Altmann, Karl-Heinz

    2015-01-01

    The xenicanes are a large class of mostly bicyclic marine diterpenoids featuring a cyclononane ring as a common structural denominator. After a brief introduction into the characteristic structural features of xenicanes and some biogenetic considerations, the major focus of this review will be on the various biological activities that have been reported for xenicanes and on efforts towards the total synthesis of these structures. Several xenicanes have been shown to be potent antiproliferative agents in vitro, but activities have also been reported in relation to inflammatory processes. However, so far, data on the possible in vivo activity of xenicanes are lacking. The major challenge in the total synthesis of xenicanes is the construction of the nine-membered ring. Different strategies have been pursued to establish this crucial substructure, including Grob fragmentation, ring-closing olefin metathesis, or Suzuki cross coupling as the enabling transformations. PMID:26429717

  14. Total synthesis of an oxepine natural product, (±)-janoxepin.

    Science.gov (United States)

    Doveston, Richard G; Steendam, René; Jones, Stuart; Taylor, Richard J K

    2012-02-17

    The total synthesis of (±)-janoxepin, a novel antiplasmodial d-leucine derived oxepine-pyrimidinone-ketopiperazine isolated from the fungus Aspergillus janus, is described. The cornerstones of the synthetic route are pyrimidinone preparation, ring-closing metathesis, aldol introduction of the enamide, and dihydro-oxepine elaboration. This synthetic route proved very efficient for the formation of a number of janoxepin analogues, including dihydro-janoxepin and tetrahydro-janoxepin. PMID:22288766

  15. Total synthesis and development of bioactive natural products

    OpenAIRE

    TATSUTA, Kuniaki

    2008-01-01

    The first total synthesis and development of a variety of bioactive natural products have been accomplished by using carbohydrates as a chiral source. In addition, practically useful intermediates have been created, analogs of natural products have been prepared, their structure-activity relationships studied, and the large-scale preparations of medicinally useful compounds established. The key target molecules have been the “Big Four” antibiotics (macrolides, aminoglycosides, β-lactams and t...

  16. First total synthesis of two nematicidal prenylated flavanones

    Institute of Scientific and Technical Information of China (English)

    Jin Hui Yang; Shi Zhi Jiang; Yan Min Zhao; Yun Feng Li; Cong Bin Ji; Wan Yi Liu

    2009-01-01

    The total synthesis of(±)-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one and(±)-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one was first achieved through C-prenylation,protection of phenolic hydroxyl group,aldol condensation,cyclization and deprotection starting from cheap benzaldehyde,4-hydroxybenzaldehyde and 2-hydroxyacetophenone,with total yield of 20 and 16.3%.All structures of new compounds were confirmed by IR,1H NMR and MS.

  17. [Biomimetic sensors in biomedical research].

    Science.gov (United States)

    Gayet, Landry; Lenormand, Jean-Luc

    2015-01-01

    The recent research on both the synthesis of membrane proteins by cell-free systems and the reconstruction of planar lipid membranes, has led to the development of a cross-technology to produce biosensors or filters. Numerous biomimetic membranes are currently being standardized and used by the industry, such as filters containing aquaporin for water desalination, or used in routine at the laboratory scale, for example the bacteriorhodopsin as a light sensor. In the medical area, several fields of application of these biomimetic membranes are under consideration today, particularly for the screening of therapeutic molecules and for the developing of new tools in diagnosis, patient monitoring and personalized medicine. PMID:26152170

  18. Synthesis of derivatives of tetronic acid and pulvinic acid. Total synthesis of norbadione A

    International Nuclear Information System (INIS)

    When vegetables like mushrooms are contaminated by radioactive caesium 137, this radioactive caesium is associated to norbadione A, a natural pigment present in two mushroom species and which can be used as a caesium decorporation agent or maybe as protection agent against ionizing radiations. Within this perspective, this research report describes the biosynthesis and the structure and properties of the norbadione A and of pulvinic acids (physicochemical properties, anti-oxidizing properties). Then, it presents the various tetronic acids (3-acyl-, 3-alkyl-, 3-alkoxy-, 3-aryl-tetronic acids and non 3-substituted tetronic acids), their synthesis path as they are described in the literature, and presents a new synthesis approach using a tandem reaction (with different esters or hydroxy esters) and the synthesis of tetronic acids. The author also proposes a new synthesis way for methyl pulvinates, and finally reports the work on the development of a total synthesis of the norbadione A

  19. Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

    Science.gov (United States)

    Bai, Yu; Shen, Xingyu; Li, Yong; Dai, Mingji

    2016-08-31

    Spinosyn A (1), a complex natural product featuring a unique 5,6,5,12-fused tetracyclic core structure, is the major component of spinosad, an organic insecticide and an FDA-approved agent used worldwide. Herein, we report an efficient total synthesis of (-)-spinosyn A with 15 steps in the longest linear sequence and 23 steps total from readily available compounds 14 and 23. The synthetic approach features several important catalytic transformations including a chiral amine-catalyzed intramolecular Diels-Alder reaction to afford 22 in excellent diastereoselectivity, a one-step gold-catalyzed propargylic acetate rearrangement to convert 28 to α-iodoenone 31, an unprecedented palladium-catalyzed carbonylative Heck macrolactonization to form the 5,12-fused macrolactone in one step, and a gold-catalyzed Yu glycosylation to install the challenging β-forosamine. This total synthesis is highly convergent and modular, thus offering opportunities to synthesize spinosyn analogues in order to address the emerging cross-resistance problems. PMID:27510806

  20. First total synthesis of four natural prenylated flavonoids

    Institute of Scientific and Technical Information of China (English)

    Jin Hui Yang; Wu Biao Zuo; Dong Dong Guo; Jun Shan Luo; Wen Qian Huang

    2012-01-01

    A facile approach for the first total synthesis of prenylated flavonoids,(±)-abyssinone-Ⅵ-4-O-methyl ether 1,(±)-abyssinone-Ⅳ-4'-O-methyl ether 2,(±)-abyssinone-Ⅴ-4'-O-methyl ether 3 and (±)-sigmoidin E 4 has been described.The key intermediate 4-hydroxy-3,5-di-(3-methylbut-2-enyl)benzaldehyde 6 was also first synthesized that features regioselective prenylation of 4-hydroxybenzaldehyde and crystallizing with petroleum ether from the reaction mixture by freeze-out effect.

  1. Total Synthesis and Biological Assessment of Mandelalide A.

    Science.gov (United States)

    Brütsch, Tobias Michael; Bucher, Pascal; Altmann, Karl-Heinz

    2016-01-22

    A new convergent total synthesis of the marine macrolide mandelalide A (1) has been developed that is based on macrocyclic ring closure by a Shiina-type macrolactonization and the construction of the requisite precursor seco acid by a highly efficient Sonogashira cross-coupling reaction between two fragments of comparable complexity. Key steps in the elaboration of the acid building block were the enantioselective, catalytic addition of a protected acetylene to crotonaldehyde and the construction of the tetrahydropyran unit that is embedded in the macrocycle by means of an acid-catalyzed Prins reaction. The synthesis of the alcohol fragment features the formation of the trisubstituted tetrahydrofuran ring through an acetal cleavage/epoxide opening cascade reaction and a rarely used radical alkynylation of a primary alkyl iodide. Intriguingly, the dihydroxylation of a terminal double bond as part of the synthesis of this building block gave the same major product for both the α- and β-AD-mix reagents, albeit with moderate or low selectivity. Synthetic mandelalide A (1) was a potent proliferation inhibitor of A549, HT460, and H1299 human lung cancer cells in vitro, but not of SK-N-SH neuroblastoma cells. However, in no case did we observe complete cell kill even at the highest compound concentration tested (5 μm). PMID:26639765

  2. Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?

    Directory of Open Access Journals (Sweden)

    Stefan Matile

    2001-10-01

    Full Text Available We report that a subtle balance of carbanion reactivity, leaving group activation, and pKa of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshida (Tetrahedron Lett. 1978, 19, 367.

  3. Cobalt-catalyzed diastereoselective synthesis of C-furanosides. Total synthesis of (-)-isoaltholactone.

    Science.gov (United States)

    Nicolas, Lionel; Izquierdo, Eva; Angibaud, Patrick; Stansfield, Ian; Meerpoel, Lieven; Reymond, Sébastien; Cossy, Janine

    2013-12-01

    An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (-)-isoaltholactone. PMID:24127819

  4. Sustainable Biomimetic Approach to Nanomaterials and Applications of Nano-Catalysts in Green Synthesis and Environmental Remediation.

    Science.gov (United States)

    The presentation summarizes our sustainable chemical synthesis activity involving benign alternatives, such as the use of supported reagents, and greener reaction medium in aqueous or solvent-free conditions. The synthesis of heterocyclic compounds, coupling reactions, and a vari...

  5. Total synthesis of discodermolide: optimization of the effective synthetic route.

    Science.gov (United States)

    de Lemos, Elsa; Porée, François-Hugues; Bourin, Arnaud; Barbion, Julien; Agouridas, Evangelos; Lannou, Marie-Isabelle; Commerçon, Alain; Betzer, Jean-François; Pancrazi, Ange; Ardisson, Janick

    2008-01-01

    An efficient and modulable total synthesis of discodermolide (DDM), a unique marine anticancer polyketide is described including related alternative synthetic approaches. Particularly notable is the repeated application of a crotyltitanation reaction to yield homoallylic (Z)-O-ene-carbamate alcohols with excellent selectivity. Advantage was taken of this reaction not only for the stereocontrolled building of the syn-anti methyl-hydroxy-methyl triads of DDM, but also for the direct construction of the terminal (Z)-diene. Of particular interest is also the installation of the C13=C14 (Z)-double bond through a highly selective dyotropic rearrangement. The preparation of the middle C8-C14 fragment in two sequential stages and its coupling to the C1-C7 moiety was a real challenge and required careful optimization. Several synthetic routes were explored to allow high and reliable yields. Due to the flexibility and robust character of this approach, it might enable a systematic structural variation of DDM and, therefore, the elaboration and exploration of novel discodermolide structural analogues.

  6. Total Synthesis of Natural Products Using Hypervalent Iodine Reagents

    Science.gov (United States)

    Maertens, Gaetan; L'homme, Chloe; Canesi, Sylvain

    2014-12-01

    We present a review of natural product syntheses accomplished in our laboratory during the last five years. Each synthetic route features a phenol dearomatization promoted by an environmentally benign hypervalent iodine reagent. The dearomatizations demonstrate the “aromatic ring umpolung” concept, and involve stereoselective remodeling of the inert unsaturations of a phenol into a highly functionalized key intermediate that may contain a quaternary carbon center and a prochiral dienone system. Several new oxidative strategies were employed, including transpositions (1,3-alkyl shift and Prins-pinacol), a polycyclization, an ipso rearrangement, and direct nucleophilic additions at the phenol para position. Several alkaloids, heterocyclic compounds, and a polycyclic core have been achieved, including sceletenone (a serotonin reuptake inhibitor), acetylaspidoalbidine (an antitumor agent), fortucine (antiviral and antitumor), erysotramidine (curare-like effect), platensimycin (an antibiotic), and the main core of a kaurane diterpene (immunosuppressive agent and stimulator of apoptosis). These concise and in some cases enantioselective syntheses effectively demonstrate the importance of hypervalent iodine reagents in the total synthesis of bioactive natural products.

  7. Total Synthesis of Natural Products Using Hypervalent Iodine Reagents

    Directory of Open Access Journals (Sweden)

    Gaetan eMaertens

    2015-01-01

    Full Text Available We present a review of natural product syntheses accomplished in our laboratory during the last five years. Each synthetic route features a phenol dearomatization promoted by an environmentally benign hypervalent iodine reagent. The dearomatizations demonstrate the aromatic ring umpolung concept, and involve stereoselective remodeling of the inert unsaturations of a phenol into a highly functionalized key intermediate that may contain a quaternary carbon center and a prochiral dienone system. Several new oxidative strategies were employed, including transpositions (1,3-alkyl shift and Prins-pinacol, a polycyclization, an ipso rearrangement, and direct nucleophilic additions at the phenol para position. Several alkaloids, heterocyclic compounds, and a polycyclic core have been achieved, including sceletenone (a serotonin reuptake inhibitor, acetylaspidoalbidine (an antitumor agent, fortucine (antiviral and antitumor, erysotramidine (curare-like effect, platensimycin (an antibiotic, and the main core of a kaurane diterpene (immunosuppressive agent and stimulator of apoptosis. These concise and in some cases enantioselective syntheses effectively demonstrate the importance of hypervalent iodine reagents in the total synthesis of bioactive natural products.

  8. Bioorganometallic chemistry: biocatalytic oxidation reactions with biomimetic nad+/nadh co-factors and [cp*rh(bpy)h]+ for selective organic synthesis

    Energy Technology Data Exchange (ETDEWEB)

    Lutz, Jochen; Hollman, Frank; Ho, The Vinh; Schnyder, Adrian; Fish, Richard H.; Schmid, Andreas

    2004-03-09

    The biocatalytic, regioselective hydroxylation of 2-hydroxybiphenyl to the corresponding catechol was accomplished utilizing the monooxygenase 2-hydroxybiphenyl 3-monooxygenase (HbpA). The necessary natural nicotinamide adenine dinucleotide (NAD{sup +}) co-factor for this biocatalytic process was replaced by a biomimetic co-factor, N-benzylnicotinamide bromide, 1a. The interaction between the flavin (FAD) containing HbpA enzyme and the corresponding biomimetic NADH compound, N-benzyl-1,4-dihdronicotinamide, 1b, for hydride transfers, was shown to readily occur. The in situ recycling of the reduced NADH biomimic 1b from 1a was accomplished with [Cp*Rh(bpy)H](Cl); however, productive coupling of this regeneration reaction to the enzymatic hydroxylation reaction was not totally successful, due to a deactivation process concerning the HbpA enzyme peripheral groups; i.e., -SH or -NH{sub 2} possibly reacting with the precatalyst, [Cp*Rh(bpy)(H{sub 2}O)](Cl){sub 2}, and thus inhibiting the co-factor regeneration process. The deactivation mechanism was studied, and a promising strategy of derivatizing these peripheral -SH or -NH{sub 2} groups with a polymer containing epoxide was successful in circumventing the undesired interaction between HbpA and the precatalyst. This latter strategy allowed tandem co-factor regeneration using 1a or 2a, [Cp*Rh(bpy)(H2O)](Cl){sub 2}, and formate ion, in conjunction with the polymer bound, FAD containing HbpA enzyme to provide the catechol product.

  9. First total synthesis and stereochemical revision of laxaphycin B and its extension to lyngbyacyclamide A.

    Science.gov (United States)

    Boyaud, France; Mahiout, Zahia; Lenoir, Christine; Tang, Shoubin; Wdzieczak-Bakala, Joanna; Witczak, Anne; Bonnard, Isabelle; Banaigs, Bernard; Ye, Tao; Inguimbert, Nicolas

    2013-08-01

    The first total synthesis of laxaphycin B was accomplished through stepwise automated Solid Phase Peptide Synthesis (SPPS), leading to the structural revision of its stereochemistry especially with regard to the configuration of one of the two 3-hydroxyleucines of this cyclic dodecapeptide of marine origin. The analogous Lyngbyacyclamide A was obtained by an extension of this synthesis.

  10. Aloe vera Induced Biomimetic Assemblage of Nucleobase into Nanosized Particles

    OpenAIRE

    Chauhan, Arun; Zubair, Swaleha; Sherwani, Asif; Owais, Mohammad

    2012-01-01

    Aim Biomimetic nano-assembly formation offers a convenient and bio friendly approach to fabricate complex structures from simple components with sub-nanometer precision. Recently, biomimetic (employing microorganism/plants) synthesis of metal and inorganic materials nano-particles has emerged as a simple and viable strategy. In the present study, we have extended biological synthesis of nano-particles to organic molecules, namely the anticancer agent 5-fluorouracil (5-FU), using Aloe vera lea...

  11. Substrate-Controlled Asymmetric Total Synthesis and Structure Revision of (-)-Bisezakyne A.

    Science.gov (United States)

    Shin, Iljin; Lee, Dongjoo; Kim, Hyoungsu

    2016-09-01

    The first asymmetric total synthesis and subsequent structure revision of (-)-bisezakyne A, a Laurencia C15 acetogenin from Alpysia oculifera, has been accomplished. Our substrate-controlled synthesis of this oxolane natural product features a highly stereoselective "protecting-group-dependent" intramolecular amide enolate alkylation strategy for the synthesis of the key 9,10-trans-9,12-cis-10-hydroxytetrahydrofuran intermediate through "nonchelate" control. In addition, our synthesis determined the absolute configuration of the halogenated marine natural product. PMID:27551943

  12. Raw Materials Synthesis from Heavy Metal Industry Effluents with Bioremediation and Phytomining: A Biomimetic Resource Management Approach

    Directory of Open Access Journals (Sweden)

    Salmah B. Karman

    2015-01-01

    Full Text Available Heavy metal wastewater poses a threat to human life and causes significant environmental problems. Bioremediation provides a sustainable waste management technique that uses organisms to remove heavy metals from contaminated water through a variety of different processes. Biosorption involves the use of biomass, such as plant extracts and microorganisms (bacteria, fungi, algae, yeast, and represents a low-cost and environmentally friendly method of bioremediation and resource management. Biosorption-based biosynthesis is proposed as a means of removing heavy metals from wastewaters and soils as it aids the development of heavy metal nanoparticles that may have an application within the technology industry. Phytomining provides a further green method of managing the metal content of wastewater. These approaches represent a viable means of removing toxic chemicals from the effluent produced during the process of manufacturing, and the bioremediation process, furthermore, has the potential to save metal resources from depletion. Biomimetic resource management comprises bioremediation, biosorption, biosynthesis, phytomining, and further methods that provide innovative ways of interpreting waste and pollutants as raw materials for research and industry, inspired by materials, structures, and processes in living nature.

  13. Biomimetic synthesis of poly(lactic-co-glycolic acid/multi-walled carbon nanotubes/apatite composite membranes

    Directory of Open Access Journals (Sweden)

    H. L. Zhang

    2012-08-01

    Full Text Available Bioactive guided tissue regeneration (GTR membrane has had some success for periodontal therapy. In this study, poly(lactic-co-glycolic acid (PLGA/multi-walled carbon nanotubes (MWNTs composite membranes were incubated in three supersaturated calcification solutions (SCS of different pH values for 21 days to prepare a PLGA/MWNTs/apatite composite. Scanning electron microscope (SEM, X-ray diffraction (XRD, Fourier transform infrared spectroscopy (FTIR, energy dispersive spectroscopy (EDS, water contact angle measurement and mechanical testing were used for characterization. It was found that after 21 days incubation, apatite with low crystallite size and crystallinity was formed on the PLGA/MWNTs composite membranes. The Ca-poor carbapatite was similar in morphology and composition to that of natural bone. The size and shape of the apatite crystals immersed in three SCS were different from each other. The hydrophilicity and mechanical properties of the PLGA/MWNTs composite membranes were significantly enhanced after mineralization. This indicated that biomimetic mineralization may be an effective method to improve the biocompatibility and bone inductivity of certain materials. The PLGA/MWNTs/apatite composites may be potentially useful in GTR applications, particularly as GTR membranes for periodontal tissue regeneration.

  14. Synthesis of 1-Substituted Isoquinolines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Cassiarin A.

    Science.gov (United States)

    Gutiérrez, Sara; Coppola, Anna; Sucunza, David; Burgos, Carolina; Vaquero, Juan J

    2016-07-15

    A new method for the synthesis of 1-substituted isoquinolines by a heterocyclization that involves α-benzyl TosMIC derivatives and different electrophiles has been developed. This methodology has been successfully applied to a total synthesis of cassiarin A, an alkaloid with potent antiplasmodial activity against Plasmodium falciparum. PMID:27351205

  15. The CP molecule labyrinth: a paradigm of how endeavors in total synthesis lead to discoveries and inventions in organic synthesis.

    Science.gov (United States)

    Nicolaou, K C; Baran, Phil S

    2002-08-01

    Imagine an artist carving a sculpture from a marble slab and finding gold nuggets in the process. This thought is not a far-fetched description of the work of a synthetic chemist pursuing the total synthesis of a natural product. At the end of the day, he or she will be judged by the artistry of the final work and the weight of the gold discovered in the process. However, as colorful as this description of total synthesis may be, it does not entirely capture the essence of the endeavor, for there is much more to be told, especially with regard to the contrast of frustrating failures and exhilarating moments of discovery. To fully appreciate the often Herculean nature of the task and the rewards that accompany it, one must sense the details of the enterprise behind the scenes. A more vivid description of total synthesis as a struggle against a tough opponent is perhaps appropriate to dramatize these elements of the experience. In this article we describe one such endeavor of total synthesis which, in addition to reaching the target molecule, resulted in a wealth of new synthetic strategies and technologies for chemical synthesis. The total synthesis of the CP molecules is compared to Theseus' most celebrated athlos (Greek for exploit, accomplishment): the conquest of the dreaded Minotaur, which he accomplished through brilliance, skill, and bravery having traversed the famous labyrinth with the help of Ariadne. This story from Greek mythology comes alive in modern synthetic expeditions toward natural products as exemplified by the total synthesis of the CP molecules which serve as a paradigm for modern total synthesis endeavors, where the objectives are discovery and invention in the broader sense of organic synthesis. PMID:12203464

  16. Total synthesis and evaluation of [18F]MHMZ

    DEFF Research Database (Denmark)

    Herth, Matthias M; Debus, Fabian; Piel, Markus;

    2008-01-01

    Radiochemical labeling of MDL 105725 using the secondary labeling precursor 2-[(18)F]fluoroethyltosylate ([(18)F]FETos) was carried out in yields of approximately 90% synthesizing [(18)F]MHMZ in a specific activity of approximately 50MBq/nmol with a starting activity of approximately 3GBq. Overall...... radiochemical yield including [(18)F]FETos synthon synthesis, [(18)F]fluoroalkylation and preparing the injectable [(18)F]MHMZ solution was 42% within a synthesis time of approximately 100 min. The novel compound showed excellent specific binding to the 5-HT(2A) receptor (K(i)=9.0 nM) in vitro and promising in...

  17. Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.

    Science.gov (United States)

    Sharpe, Robert J; Johnson, Jeffrey S

    2015-10-01

    An enantioselective synthesis of the indole diterpenoid natural product paspaline is disclosed. Critical to this approach was the implementation of stereoselective desymmetrization reactions to assemble key stereocenters of the molecule. The design and execution of these tactics are described in detail, and a thorough analysis of observed outcomes is presented, ultimately providing the title compound in high stereopurity. This synthesis provides a novel template for preparing key stereocenters in this family of molecules, and the reactions developed en route to paspaline present a series of new synthetic disconnections in preparing steroidal natural products.

  18. A Concise Total Synthesis of S-(+)-Tylophorine

    Institute of Scientific and Technical Information of China (English)

    JIN,Zhong; WANG,Qing-Min; LI,Hao; LIU,Yu-Xiu; LI,Shi-Pu; HUANG,Run-Qiu

    2004-01-01

    @@ Phenanthroindolizidine alkaloids, which exhibit extensively biological properties, are widely present at various plants of the Asclepiadaceae family.[1] The significantly biological importance of these natural products has attracted considerable synthetic efforts.[2] We herein report an efficiently asyinmetric synthesis of S-(+)-tylophorine (1), as a typically representative alkaloids.

  19. The Catalytic Enantioselective Total Synthesis of (+)‐Liphagal

    DEFF Research Database (Denmark)

    Day, Joshua J.; McFadden, Ryan M.; Virgil, Scott C.;

    2011-01-01

    catalysis, and an intramolecular aryne capture cyclization reaction. Pivotal to the successful completion of the synthesis was a sequence involving ring expansion from a [6-5-4] tricycle to a [6-7] bicyclic core followed by stereoselective hydrogenation of a sterically occluded tri-substituted olefin...

  20. The total chemical synthesis of polymer/graphene nanocomposite films.

    Science.gov (United States)

    Salvatierra, Rodrigo V; Cava, Carlos E; Roman, Lucimara S; Oliveira, Marcela M; Zarbin, Aldo J G

    2016-01-28

    A versatile and room temperature synthesis of thin films of polymer/graphene is reported. Drastically differing from other methods, not only the polymer but also the graphene are completely built from their simplest monomers (thiophene and benzene) in a one-pot polymerization reaction at a liquid-liquid interface. The materials were characterized and electronic properties are presented. PMID:26658554

  1. Lepadiformine: a case study of the value of total synthesis in natural product structure elucidation.

    Science.gov (United States)

    Weinreb, Steven M

    2003-01-01

    Since the emergence of routine X-ray crystallography and high-field FT NMR in the mid-twentieth century, the importance of total synthesis in structure elucidation has become underappreciated by most organic chemists. However, the limitations and fallibility of spectral methodology has recently been highlighted by the mischaracterization of a number of complex natural products, the correct structures of which were all ultimately assigned by total synthesis. This account describes how total synthesis was not only instrumental in disproving the erroneously assigned structure of the marine alkaloid, lepadiformine, but also was also pivotal in establishing the correct structure and absolute configuration.

  2. Progress Toward the Total Synthesis of Vinigrol and Hibarimicin B

    OpenAIRE

    Milgram, Benjamin Charles

    2013-01-01

    Vinigrol is a structurally unique diterpenoid natural product featuring a tricyclo[4.4.4.0.4a,8a]tetradecene carbon skeleton containing eight contiguous stereocenters and a challenging oxygenation pattern. Vinigrol has been demonstrated to possess a wide array of biological activities including tumor necrosis factor (TNF) antagonism, antihypertensive activity, and platelet aggregation inhibitory activity. Our first-generation plan for the synthesis of vinigrol utilized a cascade reaction sequ...

  3. Total Synthesis of Nominal Cyclocinamide B and Investigation into the Identity of the Cyclocinamides

    OpenAIRE

    Curzon, Stephanie S.; Garcia, Jessica M.; Konopelski, Joseph P.

    2014-01-01

    The total synthesis of nominal cyclocinamide B, a cyclic peptide marine natural product, is reported together with an isomer of nominal cyclocinamide A. Initial attempts at the synthesis of the title compounds by inclusion of a turn inducer failed. However, direct synthesis succeeded in formation of the 14-membered cyclic peptide structure. Comparison of the data from all synthetic cyclocinamide A and B compounds with those of the natural products leads to the conclusion that the two natural ...

  4. A strategy for complex dimer formation when biomimicry fails: total synthesis of ten coccinellid alkaloids.

    Science.gov (United States)

    Sherwood, Trevor C; Trotta, Adam H; Snyder, Scott A

    2014-07-01

    Although dimeric natural products can often be synthesized in the laboratory by directly merging advanced monomers, these approaches sometimes fail, leading instead to non-natural architectures via incorrect unions. Such a situation arose during our studies of the coccinellid alkaloids, when attempts to directly dimerize Nature's presumed monomeric precursors in a putative biomimetic sequence afforded only a non-natural analogue through improper regiocontrol. Herein, we outline a unique strategy for dimer formation that obviates these difficulties, one which rapidly constructs the coccinellid dimers psylloborine A and isopsylloborine A through a terminating sequence of two reaction cascades that generate five bonds, five rings, and four stereocenters. In addition, a common synthetic intermediate is identified which allows for the rapid, asymmetric formal or complete total syntheses of eight monomeric members of the class. PMID:24959981

  5. Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel-Crafts type cyclization.

    Science.gov (United States)

    Chen, Dong; Xu, Wen-Dan; Liu, Hao-Miao; Li, Ming-Ming; Yan, Yong-Min; Li, Xiao-Nian; Li, Yan; Cheng, Yong-Xian; Qin, Hong-Bo

    2016-06-30

    Enantioselective total synthesis of (+)-Lingzhiol has been achieved. It is the first example of in tandem semipinacol rearrangement reactions, the migrated aryl group further reacting with the carbonyl oxonium electrophile to furnish a polycyclic skeleton. Our synthesis involves 13 steps and proceeds in 6% overall yield. PMID:27321202

  6. Total synthesis and allelopathic activity of cytosporones A-C

    Energy Technology Data Exchange (ETDEWEB)

    Zamberlam, Charles E.M.; Meza, Alisson; Lima, Denis P. de; Beatriz, Adilson [Centro de Ciencias Exatas e Tecnologia, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS (Brazil); Leite, Carla Braga; Marques, Maria Rita [Centro de Ciencias Biologicas e da Saude, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS (Brazil)

    2012-07-01

    The search for efficient, environmentally friendly herbicides has been the focus of numerous studies on the organic synthesis of compounds isolated from natural sources. Cytosporones, which are phenolic lipids isolated from fungi, exhibit noteworthy biological properties. This paper reports the preparation of cytosporones A-C from the same starting material through a short synthetic route, with good yields. All compounds were tested for allelopathic activity on lettuce (Lactuca sativa L) seeds. Cytosporone A and its methylated precursor showed remarkable allelopathic activity, inhibiting seed germination and plantule growth. (author)

  7. Remarkable Stereoelectronic Effect of the Methylenedioxy Phenyl System in the Total Synthesis of Cephalotaxine

    Institute of Scientific and Technical Information of China (English)

    Hua YANG; Yong Qiang WANG; Wei DongZ. LI

    2005-01-01

    Methylenedioxyphenyl unit displays a significant stereoelectronic effect in some key transformations in the total synthesis of cephalotaxine. The ring-strain of methylenedioxy ring may account for some important facile ring-skeleton rearrangements.

  8. Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A

    DEFF Research Database (Denmark)

    Jepsen, Tue Heesgaard; Thomas, Stephen; Yunqing, lin;

    2014-01-01

    Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer...

  9. A carbohydrate approach for the formal total synthesis of (−-aspergillide C

    Directory of Open Access Journals (Sweden)

    Pabbaraja Srihari

    2014-12-01

    Full Text Available An enantioselective formal total synthesis of aspergillide C is accomplished using commercially available tri-O-acetyl-D-galactal employing a Ferrier-type C-glycosylation, utilizing a Trost hydrosilylation and protodesilylation as key reactions.

  10. Biomimetic Flow Sensors

    NARCIS (Netherlands)

    Casas, J.; Liu, Chang; Krijnen, G.J.M.

    2012-01-01

    Biomimetic flow sensors are biologically inspired devices that measure the speed and direction of fluids. This survey starts by describing the role and functioning of airflow-sensing hairs in arthropods and in fishes, carries on with the biomimetic MEMS implementations, both for air and water flow s

  11. Total Synthesis of Sporolide B and 9-epi-Sporolide B

    OpenAIRE

    Nicolaou, K. C.; Wang, Jianhua; Tang, Yefeng; Botta, Lorenzo

    2010-01-01

    The total synthesis of the structurally unique secondary metabolite sporolide B (1b, Figure 1) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system toward a number of indene derivatives as dienophiles, first in intermolecular and thence intramolecular settings. Thus, substrates were devised (37, Scheme 5; 75, Scheme 11) that underwent exquisite intramolecular [4+2] cycloaddition rea...

  12. Biomimetic High-Density Lipoproteins from a Gold Nanoparticle Template

    Science.gov (United States)

    Luthi, Andrea Jane

    For hundreds of years the field of chemistry has looked to nature for inspiration and insight to develop novel solutions for the treatment of human diseases. The ability of chemists to identify, mimic, and modifiy small molecules found in nature has led to the discovery and development of many important therapeutics. Chemistry on the nanoscale has made it possible to mimic natural, macromolecular structures that may also be useful for understanding and treating diseases. One example of such a structure is high-density lipoprotein (HDL). The goal of this work is to use a gold nanoparticle (Au NP) as a template to synthesize functional mimics of HDL and characterize their structure and function. Chapter 1 details the structure and function of natural HDL and how chemistry on the nanoscale provides new strategies for mimicking HDL. This Chapter also describes the first examples of using nanoparticles to mimic HDL. Chapter 2 reports the synthesis and characterization of biomimetic HDL using different sizes of Au NPs and different surface chemistries and how these variables can be used to tailor the properties of biomimetic HDL. From these studies the optimal strategy for synthesizing biomimetic HDL was determined. In Chapter 3, the optimization of the synthesis of biomimetic HDL is discussed as well as a full characterization of its structure. In addition, the work in this chapter shows that biomimetic HDL can be synthesized on a large scale without alterations to its structure or function. Chapter 4 focuses on understanding the pathways by which biomimetic HDL accepts cholesterol from macrophage cells. The results of these studies demonstrate that biomimetic HDL is able to accept cholesterol by both active and passive pathways of cholesterol efflux. In Chapter 5 the preliminary results of in vivo studies to characterize the pharmacokinetics and pharmacodynamics of biomimetic HDL are presented. These studies suggest that biomimetic HDL traffics through tissues prone to

  13. Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis.

    Science.gov (United States)

    Mann, Stéphane; Carillon, Sophie; Breyne, Olivier; Marquet, Andrée

    2002-01-18

    We describe the first synthesis of amiclenomycin, a natural product that has been found to inhibit biotin biosynthesis and, as a consequence, to exhibit antibiotic properties. Structure 1, with a trans relationship between the ring substituents. had previously been proposed for amiclenomycin on the basis of its 1H NMR spectrum. We have prepared the trans and cis isomers 1 and 2 by unequivocal routes and we conclude that the natural product is in fact the cis isomer 2. The properly substituted cyclohexadienyl rings were constructed first. A cycloaddition reaction between 1,2-di(phenylsulfonyl)ethylene and the N-allyloxycarbonyl diene 13, followed by reductive elimination of the phenylsulfinyl groups, gave the cis isomer 15. To obtain the trans isomer, the O-trimethylsilyl diene was used to give the cis hydroxylated Diels-Alder adduct 33, which was transformed into the corresponding trans amino derivative by means of a Mitsunobu reaction. The L-alpha-amino acid functionality was introduced by means of a Strecker reaction on the aldehydes 16 and 42, followed by enzymatic hydrolysis with immobilised pronase. PMID:11843156

  14. Biomimetic Production of Hydrogen

    Science.gov (United States)

    Gust, Devens

    2004-03-01

    The basic reaction for hydrogen generation is formation of molecular hydrogen from two electrons and two protons. Although there are many possible sources for the protons and electrons, and a variety of mechanisms for providing the requisite energy for hydrogen synthesis, the most abundant and readily available source of protons and electrons is water, and the most attractive source of energy for powering the process is sunlight. Not surprisingly, living systems have evolved to take advantage of these sources for materials and energy. Thus, biology provides paradigms for carrying out the reactions necessary for hydrogen production. Photosynthesis in green plants uses sunlight as the source of energy for the oxidation of water to give molecular oxygen, protons, and reduction potential. Some photosynthetic organisms are capable of using this reduction potential, in the form of the reduced redox protein ferredoxin, to reduce protons and produce molecular hydrogen via the action of an hydrogenase enzyme. A variety of other organisms metabolize the reduced carbon compounds that are ultimately the major products of photosynthesis to produce molecular hydrogen. These facts suggest that it might be possible to use light energy to make molecular hydrogen via biomimetic constructs that employ principles similar to those used by natural organisms, or perhaps with hybrid "bionic" systems that combine biomimetic materials with natural enzymes. It is now possible to construct artificial photosynthetic systems that mimic some of the major steps in the natural process.(1) Artificial antennas based on porphyrins, carotenoids and other chromophores absorb light at various wavelengths in the solar spectrum and transfer the harvested excitation energy to artificial photosynthetic reaction centers.(2) In these centers, photoinduced electron transfer uses the energy from light to move an electron from a donor to an acceptor moiety, generating a high-energy charge-separated state

  15. The Total Synthesis Problem of linear multivariable control. II - Unity feedback and the design morphism

    Science.gov (United States)

    Sain, M. K.; Antsaklis, P. J.; Gejji, R. R.; Wyman, B. F.; Peczkowski, J. L.

    1981-01-01

    Zames (1981) has observed that there is, in general, no 'separation principle' to guarantee optimality of a division between control law design and filtering of plant uncertainty. Peczkowski and Sain (1978) have solved a model matching problem using transfer functions. Taking into consideration this investigation, Peczkowski et al. (1979) proposed the Total Synthesis Problem (TSP), wherein both the command/output-response and command/control-response are to be synthesized, subject to the plant constraint. The TSP concept can be subdivided into a Nominal Design Problem (NDP), which is not dependent upon specific controller structures, and a Feedback Synthesis Problem (FSP), which is. Gejji (1980) found that NDP was characterized in terms of the plant structural matrices and a single, 'good' transfer function matrix. Sain et al. (1981) have extended this NDP work. The present investigation is concerned with a study of FSP for the unity feedback case. NDP, together with feedback synthesis, is understood as a Total Synthesis Problem.

  16. Total synthesis of microcin B17 via a fragment condensation approach.

    Science.gov (United States)

    Thompson, Robert E; Jolliffe, Katrina A; Payne, Richard J

    2011-02-18

    The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.

  17. Total synthesis of furospongolide and related furanolipid analogues as potential anti-tumour agents

    OpenAIRE

    Harrold, Donal Patrick

    2014-01-01

    This thesis details the design, development and execution of innovative methodology in the total synthesis of the terpene-derived marine natural product, furospongolide. It also outlines the synthetic routes used to prepare a novel range of furanolipids derivatives and subsequent evaluation of their potential as antitumour agents. The first chapter is a review of the literature describing efforts undertaken towards the synthesis of biologically active furanosesterterpenoid marine natural prod...

  18. Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin

    Energy Technology Data Exchange (ETDEWEB)

    Frederico, Daniel; Constantino, Mauricio G.; Donate, Paulo M. [Universidade de Sao Paulo (USP), Ribeirao Preto, SP (Brazil). Faculdade de Filosofia, Ciencias e Letras. Dept. de Quimica

    2009-07-01

    The total synthesis of enantiomerically enriched (3S, 5R, 3'S, 5'R)-capsorubin (1) by aldol condensation of (1R, 4S)-1-(4-hydroxy-1,2,2-trimethyl-cyclopentyl)ethanone (2a) and crocetindial (3) is described. An alternative, short eight-step synthesis of the optically active compound 2a (ee 89%) is also reported. (author)

  19. Stereoselective total synthesis of the potent anti-asthmatic compound CMI-977 (LDP-977)

    Energy Technology Data Exchange (ETDEWEB)

    Dias, Luiz Carlos; Farina, Lui Strambi; Ferreira, Marco Antonio Barbosa, E-mail: ldias@iqm.unicamp.br [Universidade de Campinas (UNICAMP), SP (Brazil). Instituto de Quimica

    2013-02-15

    A short and efficient stereoselective total synthesis of CMI-977 (LDP-977), a potent and orally active anti-asthmatic compound, was developed. The key steps involve a highly diastereoselective Mukaiyama oxidative cyclization, which provides the trans-THF (tetrahydrofuran) unit and a Seyferth-Gilbert homologation to construct the triple bond in the target molecule. The synthesis of the key chiral building block was performed using Jacobsen hydrolytic kinetic resolution. (author)

  20. Total Synthesis of Ionic Liquid Systems for Dissolution of Lunar Simulant

    Science.gov (United States)

    Sharpe, Robert J.; Karr, Laurel J.; Paley, Mark S.

    2010-01-01

    For purposes of Space Resource Utilization, work in the total synthesis of a new ionic liquid system for the extraction of oxygen and metals from lunar soil is studied and described. Reactions were carried out according to procedures found in the chemical literature, analyzed via Thin-Layer Chromatography and 1H Nuclear Magnetic Resonance Spectroscopy and purified via vacuum distillation and rotary evaporation. Upon final analysis via 1H NMR, it was found that while the intermediates of the synthesis had been achieved, unexpected side products were also present. The mechanisms and constraints of the synthesis are described as well as the final results of the project and recommendations for continued study

  1. Biomimetically inspired short access to the 2-aminoimidazole-fused tetracyclic core of (+/-)-dibromoagelaspongin.

    Science.gov (United States)

    Picon, Sylvain; Tran, Huu Dau Elise; Martin, Marie-Thérèse; Retailleau, Pascal; Zaparucha, Anne; Al-Mourabit, Ali

    2009-06-18

    A six-step synthesis of the tetracyclic core of the natural compound (+/-)-dibromoagelaspongin, isolated from Agelas sp. Sponge, was achieved from the commercially available 5-aminopentan-1-ol, 2-trichloroacetylpyrrole, and 2-aminopyrimidine. Following a biomimetic inspired approach, successive oxidative reactions including the final DMDO biomimetic oxidation gave the interesting triaminomethane-fused core. PMID:19445491

  2. Streamlined Total Synthesis of Uncialamycin and Its Application to the Synthesis of Designed Analogues for Biological Investigations.

    Science.gov (United States)

    Nicolaou, K C; Wang, Yanping; Lu, Min; Mandal, Debashis; Pattanayak, Manas R; Yu, Ruocheng; Shah, Akshay A; Chen, Jason S; Zhang, Hongjun; Crawford, James J; Pasunoori, Laxman; Poudel, Yam B; Chowdari, Naidu S; Pan, Chin; Nazeer, Ayesha; Gangwar, Sanjeev; Vite, Gregory; Pitsinos, Emmanuel N

    2016-07-01

    From the enediyne class of antitumor antibiotics, uncialamycin is among the rarest and most potent, yet one of the structurally simpler, making it attractive for chemical synthesis and potential applications in biology and medicine. In this article we describe a streamlined and practical enantioselective total synthesis of uncialamycin that is amenable to the synthesis of novel analogues and renders the natural product readily available for biological and drug development studies. Starting from hydroxy- or methoxyisatin, the synthesis features a Noyori enantioselective reduction, a Yamaguchi acetylide-pyridinium coupling, a stereoselective acetylide-aldehyde cyclization, and a newly developed annulation reaction that allows efficient coupling of a cyanophthalide and a p-methoxy semiquinone aminal to forge the anthraquinone moiety of the molecule. Overall, the developed streamlined synthesis proceeds in 22 linear steps (14 chromatographic separations) and 11% overall yield. The developed synthetic strategies and technologies were applied to the synthesis of a series of designed uncialamycin analogues equipped with suitable functional groups for conjugation to antibodies and other delivery systems. Biological evaluation of a select number of these analogues led to the identification of compounds with low picomolar potencies against certain cancer cell lines. These compounds and others like them may serve as powerful payloads for the development of antibody drug conjugates (ADCs) intended for personalized targeted cancer therapy. PMID:27266267

  3. Enantioselective Total Synthesis of (+)-Steenkrotin A and Determination of Its Absolute Configuration.

    Science.gov (United States)

    Pan, Saiyong; Gao, Beiling; Hu, Jialei; Xuan, Jun; Xie, Hujun; Ding, Hanfeng

    2016-01-18

    The first enantioselective total synthesis of (+)-steenkrotin A has been achieved in 18 steps and 4.2 % overall yield. The key features of the strategy entail a Rh-catalyzed O-H bond insertion followed by an intramolecular carbonyl-ene reaction, two sequential SmI2 -mediated Ueno-Stork and ketyl-olefin cyclizations, and a cascade intramolecular aldol condensation/vinylogous retro-aldol/aldol process with inversion of the relative configuration at the C7 position. The absolute configuration of (+)-steenkrotin A was determined based on the stepwise construction of the stereocenters during the total synthesis. PMID:26660855

  4. Synthesis of biomimetic poly[2-(methacryloyloxy)ethyl phosphorycholine]-coated magnetite nanoparticles via surface-initiated atom transfer radical polymerization.

    Science.gov (United States)

    Sui, Jie-He; Cao, Chang-Yan; Cai, Wei

    2011-10-01

    Modification of magnetite nanoparticles with biomimetic poly[2-(methacryloyloxy)ethyl phosphorycholine] (poly(MPC)) via surface-initiated atom transfer radical polymerization (ATRP) was carried out. Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analyses (TGA) and zeta potential studies indicated that well defined poly (MPC) was successfully grafted on the surface of magnetite nanoparticles. X-ray diffraction results showed the structure of magnetite nanoparticles after surface modification was not changed. The poly (MPC)-coated magnetite nanoparticles had a mean transmission electron microscopy (TEM) diameter of 11 +/- 1.5 nm. The resulting nanomaterials were superparamagnetic at room temperature, exhibited good colloidal stability in aqueous media and good responsibility to magnetic field. Such magnetite nanoparticles with biomimetic surface have potential application in prolonging circulation time in vivo.

  5. Chemistry of Renieramycins. Part 14: Total Synthesis of Renieramycin I and Practical Synthesis of Cribrostatin 4 (Renieramycin H

    Directory of Open Access Journals (Sweden)

    Masashi Yokoya

    2015-08-01

    Full Text Available The first total synthesis of (±-renieramycin I, which was isolated from the Indian bright blue sponge Haliclona cribricutis, is described. The key step is the selenium oxide oxidation of pentacyclic bis-p-quinone derivative (3 stereo- and regioselectively. We also report a large-scale synthesis of cribrostatin 4 (renieramycin H via the C3-C4 double bond formation in an early stage based on the Avendaño’s protocol, from readily available 1-acetyl-3-(3-methyl-2,4,5-trimethylphenylmethyl-piperazine-2,5-dione (8 in 18 steps (8.3% overall yield. The synthesis provides unambiguous evidence supporting the original structure of renieramycin I.

  6. Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement.

    Science.gov (United States)

    David, Nadège; Pasceri, Raffaele; Kitson, Russell R A; Pradal, Alexandre; Moody, Christopher J

    2016-07-25

    A short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors. The final route proceeds from 7-bromoindole by sequential palladium-catalysed couplings of an oxazole fragment at C-2, followed by a tyrosine fragment at C-3. With the key 2,3-disubstituted indole readily in hand, formation of a macrocyclic lactam set the stage for the crucial oxidative rearrangement to a 3,3-disubstituted oxindole. Notwithstanding the concomitant formation of the unwanted indoxyl isomer, the synthesis successfully delivered, after deprotection, the key oxindole intermediate, thereby completing a formal total synthesis of diazonamide A. PMID:27346186

  7. Catalytic Macrocyclization Strategies Using Continuous Flow: Formal Total Synthesis of Ivorenolide A.

    Science.gov (United States)

    de Léséleuc, Mylène; Godin, Éric; Parisien-Collette, Shawn; Lévesque, Alexandre; Collins, Shawn K

    2016-08-01

    A formal total synthesis of ivorenolide A has been accomplished employing a Z-selective olefin cross metathesis and a macrocyclic Glaser-Hay coupling as key steps. The macrocyclization protocol employed a phase separation/continuous flow manifold whose advantages include catalysis, fast reaction times, high concentrations, and facile scale-up. PMID:27404899

  8. The first total synthesis of the novel triquinane natural products pleurotellol and pleurotellic acid

    OpenAIRE

    Mehta, Goverdhan; Murthy, Sai Krishna A

    2003-01-01

    The first total synthesis of the triquinane based sesquiterpenoid antibiotics (±)-pleurotellol and (±)-pleurotellic acid isolated from the fermentation broth of Pleurotellus hypnophilus have been accomplished. The triquinane based bis-enone system obtained via photo-thermal metathesis in a caged pentacyclic dione has been elaborated to the natural products through carefully crafted functional group transformations.

  9. First total synthesis of yanuthones: novel farnesylated epoxycyclohexenoid marine natural products

    OpenAIRE

    Mehta, Goverdhan; Pan, Subhas Chandra

    2005-01-01

    The total synthesis of the recently isolated marine natural products of mixed biosynthetic origin, yanuthones A, 13 C and 22-deacylyanuthone A,has been accomplished following a short regio- and stereocontrolled approach involving the key intermediacy of 2-farnesyl-p-benzoquinone.

  10. Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene

    Science.gov (United States)

    Seidl, Frederick J

    2016-01-01

    Summary The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene. PMID:27559385

  11. First Total Synthesis of an Analogue of (±)—Hypargenin B

    Institute of Scientific and Technical Information of China (English)

    AnPaiLI; HuiWANG; 等

    2002-01-01

    First total synthesis of (±)-hypargenin B methyl ether 2 was accomplished via a strategy of AC→ABC,in which CrO3/H2O/NaOAc/HOAc system was utilized for introducing 7-keto group in order to aviod dehydration of benzyl tertiary alcohol.

  12. Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (-)-Lyngbyaloside B.

    Science.gov (United States)

    Fuwa, Haruhiko; Yamagata, Naoya; Okuaki, Yuta; Ogata, Yuya; Saito, Asami; Sasaki, Makoto

    2016-05-10

    We have described in detail the total synthesis of both the proposed and correct structures of (-)-lyngbyaloside B, which facilitated the elucidation of the complete stereostructure of this natural product. Our study began with the total synthesis of 13-demethyllyngbyaloside B, in which an esterification/ring-closing metathesis (RCM) strategy was successfully used for the efficient construction of the macrocycle. We also established reliable methods for the introduction of the conjugated diene side chain and the l-rhamnose residue onto the macrocyclic framework. However, the esterification/RCM strategy proved ineffective for the parent natural product because of the difficulties in acylating the sterically encumbered C-13 tertiary alcohol; macrolactionization of a seco-acid was also extensively investigated under various conditions without success. We finally completed the total synthesis of the proposed structure of (-)-lyngbyaloside B by means of a macrolactonization that involves an acyl ketene as the reactive species. However, the NMR spectroscopic data of our synthetic material did not match those of the authentic material, which indicated that the proposed structure must be re-examined. Inspection of the NMR spectroscopic data of the natural product and molecular mechanics calculations led us to postulate that the configuration of the C-10, C-11, and C-13 stereogenic centers had been incorrectly assigned in the proposed structure. Finally, our revised structure of (-)-lyngbyaloside B was unambiguously verified through total synthesis. PMID:27112323

  13. Buchner and Beyond: Arene Cyclopropanation as Applied to Natural Product Total Synthesis

    OpenAIRE

    Reisman, Sarah E.; Nani, Roger R.; Levin, Sergiy

    2011-01-01

    Buchner and Curtius first reported the cyclopropanation of arenes in 1885. Since the initial discovery, the Buchner reaction has been the subject of significant research by both physical and synthetic organic chemists. Described herein is a brief overview of the Buchner reaction and related arene cyclopropanation processes, with an emphasis on their application to natural product total synthesis.

  14. First Total Synthesis of an Analogue of (±)-Hypargenin B

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    First total synthesis of (±)-hypargenin B methyl ether 2 was accomplished via a  strategy of AC→ABC, in which CrO3/H2O/NaOAc/HOAc system was utilized for introducing  7-keto group in order to avoid dehydration of benzyl tertiary alcohol.

  15. First Total Synthesis of (±)-Abieta-8, 11, 13-trien-7β-ol

    Institute of Scientific and Technical Information of China (English)

    2003-01-01

    The first total synthesis of (±)-abieta-8, 11, 13-trien-7β-ol (7) was accomplished via a strategy of AC→ABC, in which the reduction of the ketone 6 with LiAlH4 gave exclusively the title compound.

  16. Total synthesis of exiguamines A and B inspired by catecholamine chemistry.

    Science.gov (United States)

    Sofiyev, Vladimir; Lumb, Jean-Philip; Volgraf, Matthew; Trauner, Dirk

    2012-04-16

    The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine-2,3-dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross-coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.

  17. Cu-Mediated Stille Reactions of Sterically Congested Fragments: Towards the Total Synthesis of Zoanthamine

    DEFF Research Database (Denmark)

    Nielsen, Thomas E.; Le Quement, Sebastian; Juhl, Martin;

    2005-01-01

    A study on the Stille reaction of alkenyl iodides and starmanes with structural resemblance to retrosynthetic fragments of a projected total synthesis of the marine alkaloid zoanthamine was carried out. A range of reaction conditions was examined, and a protocol developed by Corey utilizing exces...

  18. Crotylsilane reagents in the synthesis of complex polyketide natural products: total synthesis of (+)-discodermolide.

    Science.gov (United States)

    Arefolov, Alexander; Panek, James S

    2005-04-20

    An efficient, highly convergent stereocontrolled synthesis of (+)-discodermolide has been achieved with 2.1% overall yield (27 steps longest linear sequence). The absolute stereochemistry of the C1-C6 (12), C7-C14 (13), and C15-C24 (11) subunits was introduced using asymmetric crotylation methodology. Key elements of the synthesis include the use of hydrozirconation-cross-coupling methodology for the construction of C13-C14 (Z)-olefin, acetate aldol reaction to construct the C6-C7 bond and install the C7 stereocenter with high levels of 1,5-anti stereoinduction, and the use of palladium-mediated sp(2)-sp(3) cross-coupling reaction to join the advanced fragments, which assembled the carbon framework of discodermolide.

  19. Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product

    Science.gov (United States)

    Fuwa, Haruhiko

    2016-01-01

    Tetrahydropyrans are structural motifs that are abundantly present in a range of biologically important marine natural products. As such, significant efforts have been paid to the development of efficient and versatile methods for the synthesis of tetrahydropyran derivatives. Neopeltolide, a potent antiproliferative marine natural product, has been an attractive target compound for synthetic chemists because of its complex structure comprised of a 14-membered macrolactone embedded with a tetrahydropyran ring, and twenty total and formal syntheses of this natural product have been reported so far. This review summarizes the total and formal syntheses of neopeltolide and its analogues, highlighting the synthetic strategies exploited for constructing the tetrahydropyran ring. PMID:27023567

  20. A Pot-Economical Approach to the Total Synthesis of Sch-725674.

    Science.gov (United States)

    Bodugam, Mahipal; Javed, Salim; Ganguly, Arghya; Torres, Jessica; Hanson, Paul R

    2016-02-01

    A pot-economical total synthesis of antifungal Sch-725674, 1, is reported. The approach takes advantage of a number of one-pot, sequential transformations, including a phosphate tether-mediated one-pot, sequential RCM/CM/chemoselective hydrogenation protocol, a one-pot tosylation/acrylation sequence, and a one-pot, sequential Finkelstein reaction/Boord olefination/acetonide deprotection procedure to streamline the synthesis route by reducing isolation and purification procedures, thus saving time. Overall, an asymmetric route has been developed that is efficiently accomplished in seven pots from phosphate (S,S)-triene and with minimal purification. PMID:26760683

  1. The Total Synthesis of Insect Antifeedant (-)-Dihydroclerodin Starting from R-(-)-Carvone

    OpenAIRE

    Meulemans, T.M.

    2000-01-01

    The first total synthesis of the natural enantiomer of the insect-antifeedant dihydroclerodin ( 1 ) and lupulin C ( 268 ) has been achieved in 18 and 17 steps respectively starting from R-(-)-carvone ( 2 ). A new strategy was developed in which the hexahydrofuro[2,3- b ]furan fragment was introduced in the beginning of the synthesis, via a remarkably diastereoselective Mukaiyama reaction of silyl enol ether 135 with 2-methoxy-hexahydrofuro[2,3- b ]furan ( 156 ), which gave only two of the pos...

  2. Effective Length Design of Humanoid Robot Fingers Using Biomimetic Optimization

    OpenAIRE

    Byoung-Ho Kim

    2015-01-01

    In this study, we propose an effective design method for the phalangeal parameters and the total size of humanoid robot fingers based on a biomimetic optimization. For the optimization, an interphalangeal joint coordination parameter and the length constraints inherent in human fingers are considered from a biomimetic perspective. A reasonable grasp formulation is also taken into account from the viewpoint of power grasping, where the grasp space of a humanoid robot finger is importantly cons...

  3. The background of the total synthesis of yeast alanine transfer RNA

    Institute of Scientific and Technical Information of China (English)

    QI GuoRong

    2010-01-01

    @@ The research findings concerning the total synthesis of yeast alanine transfer RNA (yeast alanine tRNA) were successively published in Chinese Science Bulletin (1982) and Science in China (1983) [1].The research work started in 1968 and was finished in November 1981.It was the first artificial synthesis of a nucleic acid molecule, which followed the first artificial synthesis of protein, crystalline bovine insulin, in China in 1965, both scientific milestones occurring in China.The composition, sequence and biological functions of the synthesized nucleic acid were identical to those of the natural yeast alanine tRNA.The research lasted for 13 years.From 1982 to 1984, one of the investigators in charge of the research Prof.

  4. Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E.

    Science.gov (United States)

    Reddy, D Kumar; Shekhar, V; Prabhakar, P; Babu, D Chanti; Ramesh, D; Siddhardha, B; Murthy, U S N; Venkateswarlu, Y

    2011-02-01

    A simple, first stereoselective total synthesis of botryolide-E has been described. The synthesis started from propylene oxide employing Jacobsen's hydrolytic kinetic resolution (HKR), selective epoxide opening, sharpless asymmetric dihydroxylation, one pot acetonide deprotection and lactonization as key steps. Further, the synthesis confirms the absolute configuration of the natural product botryolide-E and we evaluated the biological behavior of natural product botryolide-E against a panel of bacteria and fungi. Botryolide-E exhibits significant potent activity against Staphylococcus aureus (MTCC 96) (6.25 μg/ml), good against Escherichia coli (MTCC 443) (12.5 μg/ml), Bacillus subtilis (MTCC 441) (25 μg/ml) and compound 1 exhibited good to moderate antifungal activity. PMID:21211971

  5. Hierarcially biomimetic bone materials: from nanometer to millimeter

    Institute of Scientific and Technical Information of China (English)

    ZHANG W.; CUI F. Z.; LIAO S. S.

    2001-01-01

    @@ The bone composite was produced by biomimetic synthesis. It shows some features of natural bone in both composition and microstructure. And the collagen moleculars and the nano-crystal hydroxyapatite assemble into ultrastructure similar to natural bone. It possesses porous structure with porosity from 100μm to 500μm after mixed with PLA (poly lactic acid).

  6. A Laboratory Exercise to Introduce Inorganic Biomimetic Compounds.

    Science.gov (United States)

    Baird, Donald M.

    1985-01-01

    Biomimetic chemistry is concerned with the synthesis of small, molecular weight molecules which mimic the properties of metal-containing sites within certain biologically significant species. A series of experiments for an advanced undergraduate laboratory is described as a way to introduce this area into the chemistry curriculum. (JN)

  7. Total synthesis of (+)-gelsemine via an organocatalytic Diels-Alder approach.

    Science.gov (United States)

    Chen, Xiaoming; Duan, Shengguo; Tao, Cheng; Zhai, Hongbin; Qiu, Fayang G

    2015-01-01

    The structurally complex alkaloid gelsemine was previously thought to have no significant biological activities, but a recent study has shown that it has potent and specific antinociception in chronic pain. While this molecule has attracted significant interests from the synthetic community, an efficient synthetic strategy is still the goal of many synthetic chemists. Here we report the asymmetric total synthesis of (+)-gelsemine, including a highly diastereoselective and enantioselective organocatalytic Diels-Alder reaction, an efficient intramolecular trans-annular aldol condensation furnishing the prolidine ring and establishing the configuration of the C20 quaternary carbon stereochemical centre. The entire gelsemine skeleton was constructed through a late-stage intramolecular SN2 substitution. The enantiomeric excess of this total synthesis is over 99%, and the overall yield is around 5%. PMID:25995149

  8. Studies towards the total synthesis of eleutherobin and other marine natural products

    OpenAIRE

    Mowat, Jeffrey Stuart

    2012-01-01

    The primary focus of the research described in this document relates to the development and application of new synthetic methodologies relevant for the concise construction of four natural products. In Chapter 2, a discussion of our investigation of the total synthesis of eleutherobin (1) is disclosed. Eleutherobin (1), first isolated in 1997 from the rare soft coral Eleutherobia sp., is a member of a class of microtubule stabilising natural products. Although it displays potent cytotoxicity,...

  9. Recent Advances in the Total Synthesis of Tetramic Acid-Containing Natural Products

    OpenAIRE

    Wen-Ju Bai; Chen Lu; Xiqing Wang

    2016-01-01

    With incredible bioactivities and fascinating structural complexities, tetramic acid- (TA-) containing natural products have attracted favorable attention among the organic chemistry community. Although the construction of the TA core is usually straightforward, the intricate C3-side chain sometimes asks for some deliberative strategy so as to fulfill an elegant total synthesis. This review mainly covers some exceptional synthetic examples for each type of natural product in recent years, sho...

  10. Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

    OpenAIRE

    John Li; May May Leong; Alastair Stewart; Mark A. Rizzacasa

    2013-01-01

    The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashira coupling between this compound and enyne 3 provided alkyne 18. Acetonide deprotection, partial red...

  11. Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach.

    Science.gov (United States)

    Smith, Amos B; Freeze, B Scott; Xian, Ming; Hirose, Tomoyasu

    2005-04-28

    [structure: see text] A highly convergent, fourth-generation total synthesis of (+)-discodermolide (1), with a longest linear sequence of 17 steps and an overall yield of 9.0%, has been achieved. Highlighting the strategy is the efficient construction and sequential, bidirectional union of a linchpin comprising the C(9)-C(14) Wittig salt-vinyl iodide (-)-18. Importantly, Wittig salt generation proceeded in excellent yield under ambient pressure.

  12. Design, total synthesis, and evaluation of C13-C14 cyclopropane analogues of (+)-discodermolide.

    Science.gov (United States)

    Smith, Amos B; Xian, Ming; Liu, Fenghua

    2005-10-13

    [structure: see text] The design, total synthesis, and biological evaluation of two C13-C14-cyclopropyl analogues [(+)-1 and (+)-2] of (+)-discodermolide have been achieved. Key features of the syntheses include highly stereoselective, hydroxyl-directed cyclopropanations of vinyl iodides and higher order cuprate-mediated cross-coupling reactions between cyclopropyl iodides and alkyl iodides. Biological evaluation revealed that neither orientation of the cyclopropyl methylene completely substitutes for the C14 methyl found in (+)-discodermolide (3).

  13. First total synthesis of the marine natural products clavulolactones II and III.

    Science.gov (United States)

    Miller, Charlotte M; Benneche, Tore; Tius, Marcus A

    2015-04-01

    The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate. Key steps involve selective TBDMS deprotection, selective reduction of the β-side chain and aldol condensation. Clavulolactones II and III were successfully prepared from (S)-4-((tert-butyldimethylsilyl)oxy) cyclopent-2-en-1-one over nine steps, in overall yields of 21 and 7% respectively. PMID:25733336

  14. Total Synthesis of (±)-Paroxetine by Diastereoconvergent Cobalt-Catalysed Arylation

    OpenAIRE

    Despiau, Carole F; Dominey, Andrew P; Harrowven, David C.; Linclau, Bruno

    2014-01-01

    A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp3–sp2 coupling reaction involving a 3-substituted 4-bromo-N-Boc-piperidine (Boc = tert-butoxycarbonyl) substrate as a key step. A 9:1 diastereoselectivity was obtained, while a control experiment involving a conformationally locked 3-substituted 4-bromo-tert-butyl cyclohexane ring proceeded with essentially complete stereoselectivity.

  15. Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), a Potent 5-Lipoxygenase Inhibitor from Honeybee Hives

    Science.gov (United States)

    Touaibia, Mohamed; Guay, Michel

    2011-01-01

    Natural products play a critical role in modern organic synthesis and learning synthetic techniques is an important component of the organic laboratory experience. In addition to traditional one-step organic synthesis laboratories, a multistep natural product synthesis is an interesting experiment to challenge students. The proposed three-step…

  16. Biomimetic synthesis of needle-like fluorescent calcium phosphate/carbon dot hybrid composites for cell labeling and copper ion detection.

    Science.gov (United States)

    Guo, Shanshan; Lu, Shousi; Xu, Pingxiang; Ma, Yi; Zhao, Liang; Zhao, Yuming; Gu, Wei; Xue, Ming

    2016-05-01

    Herein, we report a biomimetic method to synthesize needle-like calcium phosphate (CaP) with dimensions of ∼130 nm length and ∼30 nm width using carbon dots (CDs) and sodium carboxymethylcellulose as dual templates. In addition to acting as the template, the CDs enable the CaP/CDs hybrid composites to emit blue fluorescence under UV excitation. Moreover, the prepared CaP/CDs exhibited a negligible cytotoxicity towards HeLa cells. The potential of these CaP/CDs as a fluorescent probe for cell labeling was tested. In addition, it was demonstrated that the CaP/CDs were capable of selective detection of copper ions in drinking water. PMID:27052495

  17. Total Synthesis, Structure Revision, and Absolute Configuration of (−)-Brevenal

    Science.gov (United States)

    Fuwa, Haruhiko; Ebine, Makoto; Bourdelais, Andrea J.; Baden, Daniel G.; Sasaki, Makoto

    2008-01-01

    Total synthesis of structure 1 originally proposed for brevenal, a nontoxic polycyclic ether natural product isolated from the Florida red tide dinoflagellate, Karenia brevis, was accomplished. The key features of the synthesis involved (i) convergent assembly of the pentacyclic polyether skeleton based on our developed Suzuki–Miyaura coupling chemistry and (ii) stereoselective construction of the multi-substituted (E,E)-dienal side chain by using copper(I) thiophen-2-carboxylate (CuTC)-promoted modified Stille coupling. The disparity of NMR spectra between the synthetic material and the natural product required a revision of the proposed structure. Detailed spectroscopic comparison of synthetic 1 with natural brevenal, coupled with the postulated biosynthetic pathway for marine polyether natural products, suggested that the natural product was most likely represented by 2, the C26 epimer of the proposed structure 1. The revised structure was finally validated by completing the first total synthesis of (−)-2, which also unambiguously established the absolute configuration of the natural product. PMID:17177450

  18. Biomimetic sensor design

    Science.gov (United States)

    Lee, Ju Hun; Jin, Hyo-Eon; Desai, Malav S.; Ren, Shuo; Kim, Soyoun; Lee, Seung-Wuk

    2015-11-01

    Detection of desired target chemicals in a sensitive and selective manner is critically important to protect human health, environment and national security. Nature has been a great source of inspiration for the design of sensitive and selective sensors. In this mini-review, we overview the recent developments in bio-inspired sensor development. There are four major components of sensor design: design of receptors for specific targets; coating materials to integrate receptors to transducing machinery; sensitive transducing of signals; and decision making based on the sensing results. We discuss the biomimetic methods to discover specific receptors followed by a discussion about bio-inspired nanocoating material design. We then review the recent developments in phage-based bioinspired transducing systems followed by a discussion of biomimetic pattern recognition-based decision making systems. Our review will be helpful to understand recent approaches to reverse-engineer natural systems to design specific and sensitive sensors.

  19. Biomimetic hydrogel materials

    Science.gov (United States)

    Bertozzi, Carolyn; Mukkamala, Ravindranath; Chen, Qing; Hu, Hopin; Baude, Dominique

    2000-01-01

    Novel biomimetic hydrogel materials and methods for their preparation. Hydrogels containing acrylamide-functionalized carbohydrate, sulfoxide, sulfide or sulfone copolymerized with a hydrophilic or hydrophobic copolymerizing material selected from the group consisting of an acrylamide, methacrylamide, acrylate, methacrylate, vinyl and a derivative thereof present in concentration from about 1 to about 99 wt %. and methods for their preparation. The method of use of the new hydrogels for fabrication of soft contact lenses and biomedical implants.

  20. Toward the Enantioselective Total Synthesis of Lyngbyatoxin A: On the Stereocontrolled Introduction of the Quaternary Stereogenic Centre

    DEFF Research Database (Denmark)

    Tønder, Janne Ejrnæs; Tanner, David Ackland

    2003-01-01

    This paper deals with an approach to the enantioselective total synthesis of Lyngbyatoxin A, with focus on the stereocontrolled introduction of the quaternary stereogenic centre. The key step in the synthesis involves an enantiospecific Lewis-acid mediated rearrangement of chiral vinyl epoxides c...

  1. Recent Advances in the Total Synthesis of Tetramic Acid-Containing Natural Products

    Directory of Open Access Journals (Sweden)

    Wen-Ju Bai

    2016-01-01

    Full Text Available With incredible bioactivities and fascinating structural complexities, tetramic acid- (TA- containing natural products have attracted favorable attention among the organic chemistry community. Although the construction of the TA core is usually straightforward, the intricate C3-side chain sometimes asks for some deliberative strategy so as to fulfill an elegant total synthesis. This review mainly covers some exceptional synthetic examples for each type of natural product in recent years, showcasing the great achievements as well as unsettled obstacles in this area, in the hope of accelerating the synthetic and biological investigations for this unique type of natural product.

  2. Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

    Science.gov (United States)

    Dhavan, Atul A; Kaduskar, Rahul D; Musso, Loana; Scaglioni, Leonardo; Martino, Piera Anna

    2016-01-01

    Summary The first total synthesis of leopolic acid A, a fungal metabolite with a rare 2,3-pyrrolidinedione nucleus linked to an ureido dipeptide, was designed and carried out. Crucial steps for the strategy include a Dieckmann cyclization to obtain the 2,3-pyrrolidinedione ring and a Wittig olefination to install the polymethylene chain. An oxazolidinone-containing leopolic acid A analogue was also synthesized. The antibacterial activity showed by both compounds suggests that they could be considered as promising candidates for future developments. PMID:27559415

  3. Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D

    Directory of Open Access Journals (Sweden)

    Richard J. Payne

    2013-07-01

    Full Text Available The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.

  4. An approach to seco-prezizaane sesquiterpenoids: enantioselective total synthesis of (+)-1S-minwanenone.

    Science.gov (United States)

    Mehta, Goverdhan; Shinde, Harish M

    2012-09-21

    A strategy of general applicability toward seco-prezizaane sesquiterpenes, from a chiral, tricyclic synthon, readily available via an enzymatic resolution step from the Diels-Alder adduct of cyclopentadiene and p-benzoquinone, has been devised. Our approach enables harnessing of the stereochemical proclivities of the norbornyl system to install the desired stereochemistry at the key stereogenic centers. Recourse to an interesting stratagem to realign a stereochemical divergence into stereoreconvergence forms the cornerstone of our successful approach. The first total synthesis of (+)-1S-minwanenone, a prototypical member of seco-prezizaane subclass, has been accomplished. PMID:22897237

  5. Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

    Directory of Open Access Journals (Sweden)

    John Li

    2013-12-01

    Full Text Available The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1 is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashira coupling between this compound and enyne 3 provided alkyne 18. Acetonide deprotection, partial reduction and ester hydrolysis then gave resolvin D2 (1.

  6. Total Synthesis and the Biological Activities of (±-Norannuradhapurine

    Directory of Open Access Journals (Sweden)

    Surachai Nimgirawath

    2008-12-01

    Full Text Available The structure previously assigned to the phenolic noraporphine alkaloid, (--norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±-norannuradhapurine inhibits the production of NO, PGE2, TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro.

  7. Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

    Science.gov (United States)

    Dhavan, Atul A; Kaduskar, Rahul D; Musso, Loana; Scaglioni, Leonardo; Martino, Piera Anna

    2016-01-01

    Summary The first total synthesis of leopolic acid A, a fungal metabolite with a rare 2,3-pyrrolidinedione nucleus linked to an ureido dipeptide, was designed and carried out. Crucial steps for the strategy include a Dieckmann cyclization to obtain the 2,3-pyrrolidinedione ring and a Wittig olefination to install the polymethylene chain. An oxazolidinone-containing leopolic acid A analogue was also synthesized. The antibacterial activity showed by both compounds suggests that they could be considered as promising candidates for future developments.

  8. First total synthesis of 10α-hydroxy-4-muurolen-3-one and its C10-isomer

    Institute of Scientific and Technical Information of China (English)

    Fu Qiang Bi; Li Jing Fang; Chen Xi Zhang; Yu Lin Li

    2008-01-01

    An efficient synthetic route to muurolane type sesquiterpenes starting from (R)-carvone,employing allylic diazene rearrange-ment and the ring closing methesis (RCM) reaction as key steps,is described.The first asymmetric total synthesis of (-)-10α-hydroxy-4-muurolen-3-one B and (-)-10β-hydroxy-4-muurolen-3-one C was accomplished.Through the total synthesis,the absolute configurations of the natural products A,B and C were established.

  9. Tris(triazolyl)borate ligands of intermediate steric bulk for the synthesis of biomimetic structures with hydrogen bonding and solubility in hydrophilic solvents.

    Science.gov (United States)

    Gardner, Sean R; Papish, Elizabeth T; Monillas, Wesley H; Yap, Glenn P A

    2008-12-01

    Tris(triazolyl)borate ligands (Ttz) of intermediate steric bulk were synthesized to investigate their potential for hydrogen bonding and improved solubility in hydrophilic solvents as applied to biomimetic chemistry. The crystal structure of 3-phenyl-5-methyl-1,2,4-triazole (Htz(Ph,Me)) revealed hydrogen bonding and pi stacking interactions. The new ligand salt, potassium tris(3-phenyl-5-methyl-1,2,4-triazolyl)borate (KTtz(Ph,Me)) was synthesized as the first example of a Ttz ligand of intermediate steric bulk. Metathesis between KTtz(Ph,Me) and NaCl followed by recrystallization produced [NaTtz(Ph,Me)].6CH3OH in which the geometry around the sodium is octahedral with an unusual N(3)O(3) donor set; this structure also shows that a hydrogen bonding network is formed by methanol molecules and triazole nitrogens. (Ttz(Ph,Me))ZnCl was synthesized and characterized crystallographically as [(Ttz(Ph,Me))ZnCl].0.5CH3OH in which the zinc is tetrahedral and the triazole rings are within hydrogen bonding distance of CH(3)OH. All of these new compounds are methanol soluble to varying degrees and Htz(Ph,Me) and KTtz(Ph,Me) are soluble in methanol/water mixtures. PMID:18848725

  10. Biomimetic synthesis and characterization of semiconducting hybrid organic–inorganic composite materials based on polyaniline–polyethylene glycol–CdS system

    Indian Academy of Sciences (India)

    A Singh; N P Singh; R A Singh

    2011-07-01

    Triple hybrid materials based on polyaniline-polyethylene glycol and cadmium sulphide have been prepared by the duffusion–limited biomimetic route and characterized by a number of spectroscopic, XRD, SEM, thermal and electrical measurements. These hybrid materials have been prepared by controlled precipitation of cadmium sulphide by passing H2S gas and mixing the resultant colloid with the acidic solution of aniline. in situ polymerization of adsorbed anilinium ions on anionic surface of CdS resulted in hybrids. Water–soluble polyethylene glycol led to diffusion–limited growth of polyaniline and CdS resulting in a nanosized hybrid material as indicated by UV-visible spectra, X-ray diffraction (XRD) and scanning electron microscopy (SEM). AC impedance spectroscopic studies on binary and ternary nanocomposites of polyaniline with polyethylene glycol and cadmium sulphide separately and triple hybrid system have been reported. Equivalent circuits were determined and discussed in the light of contributions made from different sources such as grain, grain boundary and electrode.

  11. Synthesis of derivatives of tetronic acid and pulvinic acid. Total synthesis of norbadione A; Synthese de derives de l'acide tetronique et de l'acide pulvinique. Synthese totale de la norbadione A

    Energy Technology Data Exchange (ETDEWEB)

    Mallinger, A

    2008-11-15

    When vegetables like mushrooms are contaminated by radioactive caesium 137, this radioactive caesium is associated to norbadione A, a natural pigment present in two mushroom species and which can be used as a caesium decorporation agent or maybe as protection agent against ionizing radiations. Within this perspective, this research report describes the biosynthesis and the structure and properties of the norbadione A and of pulvinic acids (physicochemical properties, anti-oxidizing properties). Then, it presents the various tetronic acids (3-acyl-, 3-alkyl-, 3-alkoxy-, 3-aryl-tetronic acids and non 3-substituted tetronic acids), their synthesis path as they are described in the literature, and presents a new synthesis approach using a tandem reaction (with different esters or hydroxy esters) and the synthesis of tetronic acids. The author also proposes a new synthesis way for methyl pulvinates, and finally reports the work on the development of a total synthesis of the norbadione A.

  12. MIPs and Aptamers for Recognition of Proteins in Biomimetic Sensing.

    Science.gov (United States)

    Menger, Marcus; Yarman, Aysu; Erdőssy, Júlia; Yildiz, Huseyin Bekir; Gyurcsányi, Róbert E; Scheller, Frieder W

    2016-01-01

    Biomimetic binders and catalysts have been generated in order to substitute the biological pendants in separation techniques and bioanalysis. The two major approaches use either "evolution in the test tube" of nucleotides for the preparation of aptamers or total chemical synthesis for molecularly imprinted polymers (MIPs). The reproducible production of aptamers is a clear advantage, whilst the preparation of MIPs typically leads to a population of polymers with different binding sites. The realization of binding sites in the total bulk of the MIPs results in a higher binding capacity, however, on the expense of the accessibility and exchange rate. Furthermore, the readout of the bound analyte is easier for aptamers since the integration of signal generating labels is well established. On the other hand, the overall negative charge of the nucleotides makes aptamers prone to non-specific adsorption of positively charged constituents of the sample and the "biological" degradation of non-modified aptamers and ionic strength-dependent changes of conformation may be challenging in some application. PMID:27438862

  13. On the synthesis of tailored biomimetic hydroxyapatite nanoplates through a bioinspired approach in the presence of collagen or chitosan and L-arginine

    International Nuclear Information System (INIS)

    Controlling the structure of hydroxyapatite nanocrystals is vital for acquiring a consistent product. In an effort to synthesize crystals mimicking the morphology of natural bone's apatite, a bioinspired process was developed based on the use of a natural biomacromolecule, collagen or chitosan, in conjunction with L-arginine to direct the formation of hydroxyapatite from H3PO4 and Ca(OH)2. Different cases were investigated by employing various concentrations of the precursors and two molar ratios of Ca/P 1/1 and 10/6. The reaction was carried out at basic pH conditions and at biomimetic temperature (40 °C). The resulting aqueous suspensions were characterized in terms of their rheological behavior, whereas the derived powders were fully evaluated by transmission electron microscopy, Fourier transform infrared spectroscopy, X-ray diffraction analysis and Raman spectroscopy. The analysis showed that in all cases, the only phase detected was hydroxyapatite of a plate-like morphology very similar to that of natural apatite. The homogeneity of the morphology and the crystal size distribution depend on the precursors' final concentration with the mean size ranging from 5 nm up to 20 nm. The powder that demonstrated the best characteristics in terms of homogeneity was that produced in the presence of collagen for molar ratio of Ca/P 1/1. - Highlights: • Hydroxyapatite nanoplates similar to those of bone's apatite were developed. • A novel approach simulating the biomineralization environment was developed. • L-Arginine was combined with collagen or chitosan to direct HAp nucleation. • Depending on reaction conditions a very homogeneous nanostructure is attained

  14. Decision-making regarding total knee replacement surgery: A qualitative meta-synthesis

    Directory of Open Access Journals (Sweden)

    Ong Bie

    2007-04-01

    Full Text Available Abstract Background Knee osteoarthritis is a highly prevalent condition that can result in disability and reduced quality of life. The evidence suggests that total knee replacement surgery (TKR is an effective intervention for patients with severe knee problems, but there is also an unmet need for this treatment in the UK. To help understand the reason for this unmet need, the aim of this study was to explore the factors that influence the decision-making process of TKR surgery by synthesising the available evidence from qualitative research on this topic. Methods A meta-synthesis was undertaken. This involved sevens steps: getting started, deciding what is relevant to the initial interest, reading the studies, determining how the studies are related, translating the studies into one another, synthesising translations, and finally, expressing the synthesis. Second-order and third-order interpretations regarding decision-making in TKR surgery were drawn from the literature. Results Ten qualitative studies were found and are included in the synthesis. The evidence suggests that social and cultural categories of aging have shaped the expectation of knee osteoarthritis, and this in turn shapes patients' expectations of treatment options. The role of the health care professional was the strongest theme to emerge across all ten studies. Coping strategies and life context determine short and longer-term outcomes of TKR. Conclusion The decision-making process regarding TKR surgery is extremely complex, as patients have weigh up numerous considerations before they can make a decision about surgery. By synthesising ten qualitative studies, we have illuminated the importance of the health care professional during this process.

  15. Biomimetics in Tribology

    Science.gov (United States)

    Gebeshuber, I. C.; Majlis, B. Y.; Stachelberger, H.

    Science currently goes through a major change. Biology is evolving as new Leitwissenschaft, with more and more causation and natural laws being uncovered. The term `technoscience' denotes the field where science and technology are inseparably interconnected, the trend goes from papers to patents, and the scientific `search for truth' is increasingly replaced by search for applications with a potential economic value. Biomimetics, i.e. knowledge transfer from biology to technology, is a field that has the potential to drive major technical advances. The biomimetic approach might change the research landscape and the engineering culture dramatically, by the blending of disciplines. It might substantially support successful mastering of current tribological challenges: friction, adhesion, lubrication and wear in devices and systems from the meter to the nanometer scale. A highly successful method in biomimectics, the biomimicry innovation method, is applied in this chapter to identify nature's best practices regarding two key issues in tribology: maintenance of the physical integrity of a system, and permanent as well as temporary attachment. The best practices identified comprise highly diverse organisms and processes and are presented in a number of tables with detailed references.

  16. Biomimetic Cilia Based on MEMS Technology

    Institute of Scientific and Technical Information of China (English)

    Zhi-guo Zhou; Zhi-wen Liu

    2008-01-01

    A review on the research of Micro Electromechanical Systems (MEMS) technology based biomimetic cilia is presented. Biomimetic cilia, enabled by the advancement of MEMS technology, have been under dynamic development for the past decade. After a brief description of the background of cilia and MEMS technology, different biomimetic cilia applications are reviewed. Biomimetic cilia micro-actuators, including micromachined polyimide bimorph biomimetic cilia micro-actuator, electro-statically actuated polymer biomimetic cilia micro-actuator, and magnetically actuated nanorod array biomimetic cilia micro-actuator, are presented. Subsequently micromachined underwater flow biomimetic cilia micro-sensor is studied, followed by acoustic flow micro-sensor. The fabrication of these MEMS-based biomimetic cilia devices, characterization of their physical properties, and the results of their application experiments are discussed.

  17. Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products

    Directory of Open Access Journals (Sweden)

    Mankil Jung

    2012-02-01

    Full Text Available The total synthesis and structure determination of cis- and trans-flocoumafen was described. The key synthetic steps involve Knoevenagel condensation with p-methoxybenzaldehyde, in situ decarboxylation and intramolecular ring cyclization to construct the tetralone skeleton. Stereospecific reduction of the O-alkylated ketone 13 afforded good yield of precusor alcohol 5. Final coupling of alcohol 5 with 4-hydroxy-coumarin yielded flocoumafen (1. Separation and structure determination of cis- and trans-flocoumafen through 2D NMR analyses-assisted computer simulation techniques for the evaluation of anticoagulant activities are reported for the first time. This method is useful for generating the core tetralone skeleton of 4-hydroxycoumarin derivatives and provides a generalized access to various warfarin type anticoagulants.

  18. Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues.

    Science.gov (United States)

    Wang, Ruina; Liu, Guoyue; Yang, Mingyan; Wang, Mingan; Zhou, Ligang

    2016-01-01

    Total synthesis of naturally occurring spirobisnaphthalene palmarumycin CP17 and its methoxy analogues was first achieved through Friedel-Crafts acylation, Wolff-Kishner reduction, intramolecular cyclization, ketalization, benzylic oxidation, and demethylation using the inexpensive and readily available methoxybenzene, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene and 1,8-dihydroxynaphthalene as raw materials. Demethylation with (CH₃)₃SiI at ambient temperature resulted in ring A aromatization and acetal cleavage to give rise to binaphthyl ethers. The antifungal activities of these spirobisnaphthalene derivatives were evaluated, and the results revealed that 5 and 9b exhibit EC50 values of 9.34 µg/mL and 12.35 µg/mL, respectively, against P. piricola. PMID:27164077

  19. Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues

    Directory of Open Access Journals (Sweden)

    Ruina Wang

    2016-05-01

    Full Text Available Total synthesis of naturally occurring spirobisnaphthalene palmarumycin CP17 and its methoxy analogues was first achieved through Friedel-Crafts acylation, Wolff-Kishner reduction, intramolecular cyclization, ketalization, benzylic oxidation, and demethylation using the inexpensive and readily available methoxybenzene, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene and 1,8-dihydroxynaphthalene as raw materials. Demethylation with (CH33SiI at ambient temperature resulted in ring A aromatization and acetal cleavage to give rise to binaphthyl ethers. The antifungal activities of these spirobisnaphthalene derivatives were evaluated, and the results revealed that 5 and 9b exhibit EC50 values of 9.34 µg/mL and 12.35 µg/mL, respectively, against P. piricola.

  20. Total Synthesis and Anti-Viral Activities of an Extract of Radix isatidis

    Directory of Open Access Journals (Sweden)

    Li-Wei He

    2014-12-01

    Full Text Available Radix isatidis (Banlangen, a famous traditional Chinese medicine, has been used for thousands of years in China due to its anti-viral activity. Through our research, we inferred that the anti-viral activity of Radix isatidis depended on the water-soluble part. Among the components of this extract, the isoquinoline derivative 1 was isolated for the first time and has shown better anti-viral activity than other constituents. In this study, to solve the problem of sourcing sufficient quantities of compound 1, a total synthesis route is described, and several analogues are also evaluated for their anti-viral activities. Among them, compound 8 shown potent anti-viral activity with an IC50 value of 15.3 µg/mL. The results suggested that isoquinoline derivatives possessed potent anti-viral activity and are worthy further development.

  1. Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne.

    Science.gov (United States)

    Schmidt, Bernd; Audörsch, Stephan

    2016-03-01

    The first total synthesis of the polyacetylene natural product atractylodemayne A is reported. Stereoselective construction of the conjugated 8(Z),10(E)-diene moiety was achieved through a tethered ring-closing metathesis approach, comprising a Ru-catalyzed RCM followed by a base-induced elimination. A Pd-catalyzed Cadiot-Chodkiewicz coupling was used for the synthesis of the diyne. Overall, atractylodemayne A was synthesized in nine steps for the longest linear sequence. PMID:26886865

  2. Peloruside B, a Potent Antitumor Macrolide from the New Zealand Marine Sponge Mycale hentscheli: Isolation, Structure, Total Synthesis and Bioactivity

    OpenAIRE

    Singh, A. Jonathan; Xu, Chun-Xiao; Xu, Xiaoming; West, Lyndon M.; Wilmes, Anja; Chan, Ariane; Hamel, Ernest; John H Miller; Peter T. Northcote; Ghosh, Arun K.

    2010-01-01

    Peloruside B (2), a natural congener of peloruside A (1), was isolated in sub-milligram quantities from the New Zealand marine sponge Mycale hentscheli. Peloruside B promotes microtubule polymerization and arrests cells in the G2M phase of mitosis similar to paclitaxel, and its bioactivity was comparable to that of peloruside A. NMR-directed isolation, structure elucidation, structure confirmation by total synthesis and bioactivity of peloruside B are described in this article. The synthesis ...

  3. "Common synthetic scaffolds" in the synthesis of structurally diverse natural products.

    Science.gov (United States)

    Anagnostaki, Elissavet E; Zografos, Alexandros L

    2012-09-01

    Selected natural products have long been considered as desirable targets for total synthesis due to their unique biological properties and their challenging structural complexity. Laboratory synthesis of natural compounds usually relies on target-oriented synthesis, involving the production, isolation and purification of successive intermediates, requiring multiple steps to arrive to the final product. A far more economical approach using common synthetic scaffolds that can be readily transformed through biomimetic-like pathways to a range of structurally diverse natural products has been evolved in the last decade, leading synthesis to new directions. This tutorial review critically presents the hallmarks in this field.

  4. Total synthesis and structural revision of vannusals A and B: synthesis of the originally assigned structure of vannusal B.

    Science.gov (United States)

    Nicolaou, K C; Ortiz, Adrian; Zhang, Hongjun; Dagneau, Philippe; Lanver, Andreas; Jennings, Michael P; Arseniyadis, Stellios; Faraoni, Raffaella; Lizos, Dimitrios E

    2010-05-26

    The total synthesis of the originally assigned structure of vannusal B (2) and its diastereomer (d-2) are described. Initial forays into these structures with model systems revealed the viability of a metathesis-based approach and a SmI(2)-mediated strategy for the key cyclization to forge the central region of the molecule, ring C. The former approach was abandoned in favor of the latter when more functionalized substrates failed to enter the cyclization process. The successful, devised convergent strategy based on the SmI(2)-mediated ring closure utilized vinyl iodide (-)-26 and aldehyde fragment (+/-)-86 as key building blocks, whose lithium-mediated coupling led to isomeric coupling products (+)-87 and (-)-88 (as shown in Scheme 17 in the article). Intermediate (-)-88 was converted, via (-)-89 and (-)-90/(+)-91, to vannusal B structure 2 (as shown in Scheme 18 in the article), whose spectroscopic data did not match those reported for the natural product. Similarly, intermediate (+)-25, obtained through coupling of vinyl iodide (-)-26 and aldehyde (+/-)-27 (as shown in Scheme 13 in the article) was transformed via intermediates (-)-97 and (+)-98 (as shown in Scheme 19 in the article) to diastereomeric vannusal B structure (+)-d-2 (as shown in Scheme 19 in the article) which was also proven spectroscopically to be non-identical to the naturally occurring substance. These investigations led to the discovery and development of a number of new synthetic technologies that set the stage for the solution of the vannusal structural conundrum. PMID:20443561

  5. Effective Length Design of Humanoid Robot Fingers Using Biomimetic Optimization

    Directory of Open Access Journals (Sweden)

    Byoung-Ho Kim

    2015-10-01

    Full Text Available In this study, we propose an effective design method for the phalangeal parameters and the total size of humanoid robot fingers based on a biomimetic optimization. For the optimization, an interphalangeal joint coordination parameter and the length constraints inherent in human fingers are considered from a biomimetic perspective. A reasonable grasp formulation is also taken into account from the viewpoint of power grasping, where the grasp space of a humanoid robot finger is importantly considered to determine the phalangeal length parameters. The usefulness of the devised biomimetic optimization method is shown through the design examples of various humanoid robot fingers. In fact, the optimization-based finger design method enables us to determine effectively the proper phalangeal size of humanoid robot fingers for human-like object handling tasks. In addition, we discuss its contribution to the structural configuration and coordinated motion of a humanoid robot finger, and address its practical availability in terms of effective finger design.

  6. A Biomimetic Haptic Sensor

    Directory of Open Access Journals (Sweden)

    Ben Mitchinson

    2008-11-01

    Full Text Available The design and implementation of the periphery of an artificial whisker sensory system is presented. It has been developed by adopting a biomimetic approach to model the structure and function of rodent facial vibrissae. The artificial vibrissae have been formed using composite materials and have the ability to be actively moved or whisked. The sensory structures at the root of real vibrissae has been modelled and implemented using micro strain gauges and Digital Signal Processors. The primary afferents and vibrissal trigeminal ganglion have been modelled using empirical data taken from electrophysiological measurements, and implemented in real-time using a Field Programmable Gate Array. Pipelining techniques were employed to maximise the utility of the FPGA hardware. The system is to be integrated into a more complete whisker sensory model, including neural structures within the central nervous system, which can be used to orient a mobile robot.

  7. Biomimetic thin film deposition

    Energy Technology Data Exchange (ETDEWEB)

    Rieke, P.R.; Graff, G.E.; Campbell, A.A.; Bunker, B.C.; Baskaran, S.; Song, L.; Tarasevich, B.J.; Fryxell, G.E.

    1995-09-01

    Biological mineral deposition for the formation of bone, mollusk shell and other hard tissues provides materials scientists with illustrative materials processing strategies. This presentation will review the key features of biomineralization and how these features can be of technical importance. We have adapted existing knowledge of biomineralization to develop a unique method of depositing inorganic thin films and coating. Our approach to thin film deposition is to modify substrate surfaces to imitate the proteins found in nature that are responsible for controlling mineral deposition. These biomimetic surfaces control the nucleation and growth of the mineral from a supersaturated aqueous solution. This has many processing advantages including simple processing equipment, environmentally benign reagents, uniform coating of highly complex shapes, and enhanced adherence of coating. Many different types of metal oxide, hydroxide, sulfide and phosphate materials with useful mechanical, optical, electronic and biomedical properties can be deposited.

  8. Biotechnologies and biomimetics for civil engineering

    CERN Document Server

    Labrincha, J; Diamanti, M; Yu, C-P; Lee, H

    2015-01-01

    Putting forward an innovative approach to solving current technological problems faced by human society, this book encompasses a holistic way of perceiving the potential of natural systems. Nature has developed several materials and processes which both maintain an optimal performance and are also totally biodegradable, properties which can be used in civil engineering. Delivering the latest research findings to building industry professionals and other practitioners, as well as containing information useful to the public, ‘Biotechnologies and Biomimetics for Civil Engineering’ serves as an important tool to tackle the challenges of a more sustainable construction industry and the future of buildings.

  9. Total synthesis, structural, and biological evaluation of stylissatin A and related analogs.

    Science.gov (United States)

    Shaheen, Farzana; Jabeen, Almas; Ashraf, Samreen; Nadeem-Ul-Haque, Muhammad; Shah, Zafar Ali; Ziaee, Muhammad Asad; Dastagir, Nida; Ganesan, A

    2016-09-01

    The natural product cyclic peptide stylissatin A (1a) was reported to inhibit nitric oxide production in LPS-stimulated murine macrophage RAW 264.7 cells. In the current study, solid-phase total synthesis of stylissatin A was performed by using a safety-catch linker and yielded the peptide with a trans-Phe(7) -Pro(6) linkage, whereas the natural product is the cis rotamer at this position as evidenced by a marked difference in NMR chemical shifts. In order to preclude the possibility of 1b being an epimer of the natural product, we repeated the synthesis using d-allo-Ile in place of l-Ile and a different site for macrocyclization. The resulting product (d-allo-Ile(2) )-stylissatin A (1c) was also found to have the trans-Phe(7) -Pro(6) peptide conformations like rotamer 1b. Applying the second route to the synthesis of stylissatin A itself, we obtained stylissatin A natural rotamer 1a accompanied by rotamer 1b as the major product. Rotamers 1a, 1b, and the epimer 1c were separable by HPLC, and 1a was found to match the natural product in structure and biological activity. Six related analogs 2-7 of stylissatin A were synthesized on Wang resin and characterized by spectral analysis. The natural product (1a), the rotamer (1b), and (d-allo-Ile(2) )-stylissatin A (1c) exhibited significant inhibition of NO(.) . Further investigations were focused on 1b, which also inhibited proliferation of T-cells and inflammatory cytokine IL-2 production. The analogs 2-7 weakly inhibited NO(.) production, but strongly inhibited IL-2 cytokine production compared with synthetic peptide 1b. All analogs inhibited the proliferation of T-cells, with analog 7 having the strongest effect. In the analogs, the Pro(6) residue was replaced by Glu/Ala, and the SAR indicates that the nature of this residue plays a role in the biological function of these peptides. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd. PMID:27526945

  10. Concise synthetic approaches to naturally occurring β-hydroxyphenylarsonic: first total synthesis of papanerine, its derivative, and praecansone B

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Xue; Lee, Yong Rok [Yeungnam Univ., Gyeongsan (Korea, Republic of); Kim, Sung Hong [Korea Basic Science Institute, Daegu (Korea, Republic of)

    2012-04-15

    The total synthesis of biologically interesting β-hydroxyphenylarsonic, papanerine (1), its derivative 2, praecansone B (3), and pongapinone A (4) has been accomplished starting from commercially available 2,4-dihydroxyacetophenone or 6-methoxy-2,4-dihydroxyacetophenone in 3 steps by a convergent strategy through ben zopyran formations, O-methylation, and coupling reactions.

  11. Total synthesis and structural confirmation of the marine natural product Dysinosin A: a novel inhibitor of thrombin and Factor VIIa.

    Science.gov (United States)

    Hanessian, Stephen; Margarita, Roberto; Hall, Adrian; Johnstone, Shawn; Tremblay, Martin; Parlanti, Luca

    2002-11-13

    The structure and absolute configuration of the marine antithrombotic product dysinosin A was confirmed by total synthesis. The strategy involved disconnections to three subunits, of which two were synthesized from the readily available l-glutamic acid, d-leucine, and d-mannitol. The Grubbs olefin metathesis carbocyclization reaction was utilized to prepare two intermediates. PMID:12418860

  12. A Convergent Enantioselective Total Synthesis of (-)-Perhydrohistrionicotoxin with an Intramolecular Imino Ene-type Reaction as a Key Step

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Hagberg, Lars

    1998-01-01

    A convergent enantioselective total synthesis of the neurotoxic spirocyclic alkaloid (-)-perhydrohistrionicotoxin (2) is described. A Lewis acid-mediated intramolecular imine ene-type reaction was used for the key spirocyclisation step (14 to 3, with 3 being obtained as a single diastereoisomer)....

  13. A new isochroman-4-one derivative from the peel of Musa sapientum L. and its total synthesis

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A new isochroman-4-one, 7,8-dihydroxy-3-methylisochroman-4-one was isolated from water soluble fraction of Musa sapientum L. Its structure was determined by spectroscopic evidences and its total synthesis has also been reported. The compound showed potent antihypertensive activity.

  14. First total synthesis of a guanidine alkaloid Nitensidine D using immobilized ionic liquid, microwaves and formamidinesulfinic acid

    Indian Academy of Sciences (India)

    Shallu; M L Sharma; Jasvinder Singh

    2014-11-01

    An efficient first total synthesis of a naturally occurring guanidine alkaloid, Nitensidine D isolated from ethanol extract of Pterogyne nitens has been described. Geraniol has been used as the starting material. N-alkylation of phthalimide has been achieved using immobilized ionic liquid and formamidinesulfinic acid acts as the guanylating reagent.

  15. Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

    OpenAIRE

    Thilo Focken; Stephen Hanessian

    2014-01-01

    A review of the synthesis of natural products and bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be summarized, as well as an overview of the synthesis of the employed phosphonamide reagents.

  16. Concise Asymmetric Construction of C2 -symmetric 1,9-Diarylnonanoids Using a Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone.

    Science.gov (United States)

    Kotani, Shunsuke; Kai, Kosuke; Shimoda, Yasushi; Hu, Hao; Gao, Shen; Sugiura, Masaharu; Ogasawara, Masamichi; Nakajima, Makoto

    2016-02-01

    By using a phosphine oxide-catalyzed enantioselective double aldol reaction, we achieved the concise construction of C2 -symmetric 1,9-diarylnonanoids, enabling the synthesis of (-)-ericanone from p-hydroxybenzaldehyde in 6 steps with 65 % overall yield. The enantioselective double aldol reaction is useful for establishing C2 -symmetric 1,9-diaryl-3,7-dihydroxy-5-nonanones with a single operation. Furthermore, the use of o-nosyl-protected p-hydroxybenzaldehyde and a 4,4'-disubstituted BINAP dioxide catalyst dramatically improved the reactivity and selectivity in the double aldol reaction, enabling the total synthesis of (-)-ericanone with high yield and with excellent enantiopurity.

  17. Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone.

    Science.gov (United States)

    Aussedat, Baptiste; Fasching, Bernhard; Johnston, Eric; Sane, Neeraj; Nagorny, Pavel; Danishefsky, Samuel J

    2012-02-22

    Described herein is the first total chemical synthesis of the unique α-subunit of the human glycoprotein hormone (α-hGPH). Unlike the biologically derived glycoprotein hormones, which are isolated as highly complex mixtures of glycoforms, α-hGPH obtained by chemical synthesis contains discrete homogeneous glycoforms. Two such systems have been prepared. One contains the disaccharide chitobiose at the natural N-glycosylation sites. The other contains dodecamer oligosaccharides at these same sites. The dodecamer sugar is a consensus sequence incorporating the key features associated with human glycoproteins.

  18. Biomimetic strengthening polylactide scaffold materials for bone tissue engineering

    Institute of Scientific and Technical Information of China (English)

    XU Guofu; MOU Shenzhou; ZHOU Lingping; LIAO Susan; YIN Zhimin; CUI Fuzhai

    2007-01-01

    In this paper,a new polylactide(PLA)-based scaffold composite by biomimetic synthesis was designed.The novel composite mainly consists ofnano-hydroxyapatite (n-HA),which is the main inorganic content in natural bone tissue for the PLA.The crystal degree of the n-HA in the composite is low and the crystal size is very small,which is similar to that of natural bone.The compressive strength of the composite is higher than that of the PLA scaffold.Using the osteoblast culture technique,we detected cell behaviors on the biomaterial in vitro by SEM,and the cell affinity of the composite was found to be higher than that of the PLA scaffold.The biomimetic three-dimensional porous composite can serve as a kind of excellent scaffold material for bone tissue engineering because of its microstructure and properties.

  19. Biomimetic synthesis of raspberry-like hybrid polymer-silica core-shell nanoparticles by templating colloidal particles with hairy polyamine shell.

    Science.gov (United States)

    Pi, Mengwei; Yang, Tingting; Yuan, Jianjun; Fujii, Syuji; Kakigi, Yuichi; Nakamura, Yoshinobu; Cheng, Shiyuan

    2010-07-01

    The nanoparticles composed of polystyrene core and poly[2-(diethylamino)ethyl methacrylate] (PDEA) hairy shell were used as colloidal templates for in situ silica mineralization, allowing the well-controlled synthesis of hybrid silica core-shell nanoparticles with raspberry-like morphology and hollow silica nanoparticles by subsequent calcination. Silica deposition was performed by simply stirring a mixture of the polymeric core-shell particles in isopropanol, tetramethyl orthosilicate (TMOS) and water at 25 degrees C for 2.5h. No experimental evidence was found for nontemplated silica formation, which indicated that silica deposition occurred exclusively in the PDEA shell and formed PDEA-silica hybrid shell. The resulting hybrid silica core-shell particles were characterized by transmission electron microscopy (TEM), thermogravimetry, aqueous electrophoresis, and X-ray photoelectron spectroscopy. TEM studies indicated that the hybrid particles have well-defined core-shell structure with raspberry morphology after silica deposition. We found that the surface nanostructure of hybrid nanoparticles and the composition distribution of PDEA-silica hybrid shell could be well controlled by adjusting the silicification conditions. These new hybrid core-shell nanoparticles and hollow silica nanoparticles would have potential applications for high-performance coatings, encapsulation and delivery of active organic molecules. PMID:20347275

  20. Biomimetic synthesis of raspberry-like hybrid polymer-silica core-shell nanoparticles by templating colloidal particles with hairy polyamine shell.

    Science.gov (United States)

    Pi, Mengwei; Yang, Tingting; Yuan, Jianjun; Fujii, Syuji; Kakigi, Yuichi; Nakamura, Yoshinobu; Cheng, Shiyuan

    2010-07-01

    The nanoparticles composed of polystyrene core and poly[2-(diethylamino)ethyl methacrylate] (PDEA) hairy shell were used as colloidal templates for in situ silica mineralization, allowing the well-controlled synthesis of hybrid silica core-shell nanoparticles with raspberry-like morphology and hollow silica nanoparticles by subsequent calcination. Silica deposition was performed by simply stirring a mixture of the polymeric core-shell particles in isopropanol, tetramethyl orthosilicate (TMOS) and water at 25 degrees C for 2.5h. No experimental evidence was found for nontemplated silica formation, which indicated that silica deposition occurred exclusively in the PDEA shell and formed PDEA-silica hybrid shell. The resulting hybrid silica core-shell particles were characterized by transmission electron microscopy (TEM), thermogravimetry, aqueous electrophoresis, and X-ray photoelectron spectroscopy. TEM studies indicated that the hybrid particles have well-defined core-shell structure with raspberry morphology after silica deposition. We found that the surface nanostructure of hybrid nanoparticles and the composition distribution of PDEA-silica hybrid shell could be well controlled by adjusting the silicification conditions. These new hybrid core-shell nanoparticles and hollow silica nanoparticles would have potential applications for high-performance coatings, encapsulation and delivery of active organic molecules.

  1. An Improved Method of Total Synthesis of 2-Methoxypodocarpane-8,11,13-triene

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    12-Methoxypodocarpane-8,11,13-triene 1, the key intermediate in the synthesis of some important diterpenes, was synthesized in an efficient way, which has the characteristics of short route, simple operation and high yield.

  2. Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction

    Science.gov (United States)

    Baker, Joseph B.; Kim, Hyoungsu; Hong, Jiyong

    2015-01-01

    The tandem allylic oxidation/oxa-conjugate addition reaction promoted by the gem-disubstituent effect in conjunction with the NHC-mediated oxidative esterification was explored for the facile synthesis of clavosolide A. PMID:26236051

  3. Total Synthesis of ( - )-Kaerophyllin, ( - )-Hinokinin and (±)-Iso-hinokinin

    Institute of Scientific and Technical Information of China (English)

    夏亚穆; 梁其任; 王小龙; 曹小平; 潘鑫复

    2003-01-01

    A convenient and rapid approach for the syntheses of (-)-kaerophyllin (1), (-)-hinokinin (2) and (±)-isohinokinin (3) was described. The key steps were involved in condensation of aromatic aldehyde and alkylation of the resulting ester to give the complete skeleton of dibenzylbutyrolactone-lignan. Hydrolysis, followed by resolution with quinine, reduction and when appropriate, oxidation gave the title compound. The asynunetric total synthesis of the kaerophyllin (1) was reported for the first tlme.

  4. 1,6-asymmetric induction in boron-mediated aldol reactions: application to a practical total synthesis of (+)-discodermolide.

    Science.gov (United States)

    Paterson, Ian; Delgado, Oscar; Florence, Gordon J; Lyothier, Isabelle; Scott, Jeremy P; Sereinig, Natascha

    2003-01-01

    By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C(1)-C(5), C(9)-C(16), and C(17)-C(24) subunits. [reaction--see text

  5. Bio-mimetic Flow Control

    Science.gov (United States)

    Choi, Haecheon

    2009-11-01

    Bio-mimetic engineering or bio-mimetics is the application of biological methods and systems found in nature to the study and design of engineering systems and modern technology (from Wikipedia). The concept itself is old, but successful developments have been made recently, especially in the research field of flow control. The objective of flow control based on the bio-mimetic approach is to develop novel concepts for reducing drag, increasing lift and enhancing aerodynamic performance. For skin friction reduction, a few ideas have been suggested such as the riblet from shark, compliant surface from dolphin, microbubble injection and multiple front-body curvature from penguin, and V-shaped protrusion from sailfish. For form drag reduction, several new attempts have been also made recently. Examples include the V-shaped spanwise grooves from saguaro cactus, overall shape of box fish, longitudinal grooves on scallop shell, bill of swordfish, hooked comb on owl wing, trailing-edge protrusion on dragonfly wing, and fillet. For the enhancement of aerodynamic performance, focuses have been made on the birds, fish and insects: e.g., double layered feather of landing bird, leading-edge serration of humpback-whale flipper, pectoral fin of flying fish, long tail on swallowtail-butterfly wing, wing flapping motion of dragonfly, and alula in birds. Living animals adapt their bodies to better performance in multi purposes, but engineering requires single purpose in most cases. Therefore, bio-mimetic approaches often produce excellent results more than expected. However, they are sometimes based on people's wrong understanding of nature and produce unwanted results. Successes and failures from bio-mimetic approaches in flow control will be discussed in the presentation.

  6. Biomimetic fabrication of a three-level hierarchical calcium phosphate/collagen/hydroxyapatite scaffold for bone tissue engineering

    International Nuclear Information System (INIS)

    A three-level hierarchical calcium phosphate/collagen/hydroxyapatite (CaP/Col/HAp) scaffold for bone tissue engineering was developed using biomimetic synthesis. Porous CaP ceramics were first prepared as substrate materials to mimic the porous bone structure. A second-level Col network was then composited into porous CaP ceramics by vacuum infusion. Finally, a third-level HAp layer was achieved by biomimetic mineralization. The three-level hierarchical biomimetic scaffold was characterized using scanning electron microscopy, energy-dispersive x-ray spectra, x-ray diffraction and Fourier transform infrared spectroscopy, and the mechanical properties of the scaffold were evaluated using dynamic mechanical analysis. The results show that this scaffold exhibits a similar structure and composition to natural bone tissues. Furthermore, this three-level hierarchical biomimetic scaffold showed enhanced mechanical strength compared with pure porous CaP scaffolds. The biocompatibility and osteoinductivity of the biomimetic scaffolds were evaluated using in vitro and in vivo tests. Cell culture results indicated the good biocompatibility of this biomimetic scaffold. Faster and increased bone formation was observed in these scaffolds following a six-month implantation in the dorsal muscles of rabbits, indicating that this biomimetic scaffold exhibits better osteoinductivity than common CaP scaffolds. (papers)

  7. Total Chemical Synthesis,Assembly of Human Torque Teno Virus Genome

    Institute of Scientific and Technical Information of China (English)

    Zheng Hou; Gengfu Xiao

    2011-01-01

    Torque teno virus(TTV)is a nonenveloped virus containing a single-stranded,circular DNA genome of approximately 3.8kb.We completely synthesized the 3808 nucleotides of the TTV(SANBAN isolate)genome,which contains a hairpin structure and a GC-rich region.More than 100 overlapping oligonucleotides were chemically synthesized and assembled by polymerise chain assembly reaction(PCA),and the synthesis was completed with splicing by overlap extension(SOEing).This study establishes the methodological basis of the chemical synthesis of a viral genome for use as a live attenuated vaccine or gene therapy vector.

  8. Total Synthesis and Structure-Activity Relationship of Glycoglycerolipids from Marine Organisms

    Directory of Open Access Journals (Sweden)

    Jun Zhang

    2014-06-01

    Full Text Available Glycoglycerolipids occur widely in natural products, especially in the marine species. Glycoglycerolipids have been shown to possess a variety of bioactivities. This paper will review the different methodologies and strategies for the synthesis of biological glycoglycerolipids and their analogs for bioactivity assay. In addition, the bioactivities and structure-activity relationship of the glycoglycerolipids are also briefly outlined.

  9. Total synthesis of desoxycyclomarin C and the cyclomarazines A and B.

    Science.gov (United States)

    Barbie, Philipp; Kazmaier, Uli

    2016-07-01

    Removing the β-hydroxy group from the prenylated tryptophan moiety of cyclomarins simplifies the synthesis of these interesting natural products significantly, without having a noteworthy effect on the anti-tuberculosis activity of the cyclomarins. In contrast, cyclomarazines did not show biological activity. PMID:27241664

  10. Biosynthesis and Total Synthesis Studies on The Jadomycin Family of Natural Products

    OpenAIRE

    Sharif, Ehesan U.; O’Doherty, George A.

    2012-01-01

    Jadomycins are unique angucycline polyketides, which are produced by soil bacteria Streptomyces venezuelae under specific nutrient and environmental conditions. Their unique structural complexity and biological activities have engendered extensive study of the jadomycin class of natural compounds in terms of biological activity, biosynthesis, and synthesis.

  11. Total Synthesis of the Antimicrotubule Agent (+)-Discodermolide Using Boron-Mediated Aldol Reactions of Chiral Ketones.

    Science.gov (United States)

    Paterson; Florence; Gerlach; Scott

    2000-01-01

    With a similar mechanism of action to taxol, the title compound 1 is a particularly promising candidate for development in cancer chemotherapy. This efficient synthesis, based on stereocontrolled aldol reactions, should help to overcome the scarce natural supply of 1 from the rare sponge source.

  12. Biomimetic membranes for sensor and separation applications

    DEFF Research Database (Denmark)

    Helix Nielsen, Claus

    2009-01-01

    membrane-based sensor and/or separation devices? In the development of biomimetic sensor/separation technology, both channels (ion and water channels) and carriers (transporters) are important. Generally, each class of transport proteins conducts specific molecular species in and out of the cell while...... generally have a lower turnover but are capable of transport against gradients. For both classes of proteins, their unique flux-properties make them interesting as candidates in biomimetic sensor/separation devices. An ideal sensor/separation device requires the supporting biomimetic matrix to be virtually...... current developments of biomimetic sensor/separation devices....

  13. Total Synthesis of Two 4, 5-Dioxo-seco-eudesmane Sesquiterpenes

    Institute of Scientific and Technical Information of China (English)

    Li Jing FANG; Chen Xi ZHANG; Jin Chun CHEN; Guo Jun ZHENG; Yu Lin LI

    2005-01-01

    A facile synthetic route to two seco-eudesmane, 4, 5-dioxo-10-epi-4, 5-seco-γeudesmane (1) and 4, 5-dioxo-10-epi-4, 5-seco-γ-eudesmol (2) from (+)-dihydrocarvone has been described. Avoiding expensive reagents, this highly economic method especially suits for the synthesis of 4, 5-seco-eudesman-type and ophianon-type sesquiterpenes with a double bond at position 11 and 12.

  14. The Efficient and Enantiospecific Total Synthesis of Cyclopenta[b]phenanthrenes Structurally-related to Neurosteroids

    OpenAIRE

    Qian, Mingxing; Covey, Douglas F.

    2010-01-01

    We report an efficient synthesis of cyclopenta[b]phenanthrenes functionalized at C-3 and C-8 from an optically pure Hajos-Parrish ketone. The key step is a neutral alumina catalyzed Michael addition of a Hajos-Parrish ketone derivative (4) to 1,7-octadien-3-one (2) in 98% yield. This Michael addition product went through Krapcho decarbomethoxylation, aldol condensation, lithium liquid ammonia reduction, Wacker oxidation and acid catalyzed cyclization to form cyclopenta[b]phenanthrene (1a) in ...

  15. Biological and Biomimetic Comb Polyelectrolytes

    Directory of Open Access Journals (Sweden)

    Aristeidis Papagiannopoulos

    2010-05-01

    Full Text Available Some new phenomena involved in the physical properties of comb polyelectrolyte solutions are reviewed. Special emphasis is given to synthetic biomimetic materials, and the structures formed by these molecules are compared with those of naturally occurring glycoprotein and proteoglycan solutions. Developments in the determination of the structure and dynamics (viscoelasticity of comb polymers in solution are also covered. Specifically the appearance of multi-globular structures, helical instabilities, liquid crystalline phases, and the self-assembly of the materials to produce hierarchical comb morphologies is examined. Comb polyelectrolytes are surface active and a short review is made of some recent experiments in this area that relate to their morphology when suspended in solution. We hope to emphasize the wide variety of phenomena demonstrated by the vast range of naturally occurring comb polyelectrolytes and the challenges presented to synthetic chemists designing biomimetic materials.

  16. Total synthesis of the aristolochic acids, their major metabolites, and related compounds.

    Science.gov (United States)

    Attaluri, Sivaprasad; Iden, Charles R; Bonala, Radha R; Johnson, Francis

    2014-07-21

    Plants from the Aristolochia genus have been recommended for the treatment of a variety of human ailments since the time of Hippocrates. However, many species produce the highly toxic aristolochic acids (AAs), which are both nephrotoxic and carcinogenic. For the purposes of extensive biological studies, a versatile approach to the synthesis of the AAs and their major metabolites was devised based primarily on a Suzuki-Miyaura coupling reaction. The key to success lies in the preparation of a common ring-A precursor, namely, the tetrahydropyranyl ether of 2-nitromethyl-3-iodo-4,5-methylendioxybenzyl alcohol (27), which was generated in excellent yield by oxidation of the aldoxime precursor 26. Suzuki-Miyaura coupling of 27 with a variety of benzaldehyde 2-boronates was accompanied by an aldol condensation/elimination reaction to give the desired phenanthrene intermediate directly. Deprotection of the benzyl alcohol followed by two sequential oxidation steps gave the desired phenanthrene nitrocarboxylic acids. This approach was used to synthesize AAs I-IV and several other related compounds, including AA I and AA II bearing an aminopropyloxy group at position-6, which were required for further conversion to fluorescent biological probes. Further successful application of the Suzuki-Miyaura coupling reaction to the synthesis of the N-hydroxyaristolactams of AA I and AA II then allowed the synthesis of the putative, but until now elusive, N-acetoxy- and N-sulfonyloxy-aristolactam metabolites. PMID:24877584

  17. Design, synthesis, and characterization of biomimetic oligomers

    DEFF Research Database (Denmark)

    Laursen, Jonas Striegler

    . Using NMR spectroscopy, X-ray crystallographic analysis, and density functional theory (DFT) calculations, we found evidence for the presence of thioamide–aromatic interactions through Csp2-H···Samide hydrogen bonding. Based on these studies we designed a ß-peptoid oligomer from residues prone to fit......Peptides and proteins made from the 20 canonical amino acids are responsible for many processes necessary for organisms to function. Beside their composition, proteins obtain their activity and unique selectivity through an ability to display functionalities accurately in the three......, for their ability to mimic the structural elements seen in proteins. Two prominent peptidomimetics are ß-peptides and a-peptoids (N-alkylglycines), which have been shown to fold into helical and sheet-like arrangements. To expand the chemical space available for mimicking protein structure their features have been...

  18. Influence of the Total Gas Flow at Different Reaction Times for CVD-Graphene Synthesis on Polycrystalline Nickel

    Directory of Open Access Journals (Sweden)

    M. P. Lavin-Lopez

    2016-01-01

    Full Text Available Optimization of the total gas flow (CH4+H2 during the reaction step for different reaction times for CVD-graphene synthesis on polycrystalline nickel foil using an atmospheric pressure set-up is reported. A thickness value related to number of graphene layers in each of the synthesized samples was determined using an Excel-VBA application. This method assigned a thickness value between 1 and 1000 and provided information on the percentage of each type of graphene (monolayer, bilayer, and multilayer deposited onto the polycrystalline nickel sheet. The influence of the total gas flow during the reaction step and the reaction time was studied in detail. Optical microscopy showed that samples were covered with different types of graphene, such as multilayer, few-layer, bilayer, and monolayer graphene. The synthesis variables were optimized according to the thickness value and the results were verified by Raman spectroscopy. The best conditions were obtained with a reaction temperature of 980°C, a CH4/H2 flow rate ratio of 0.07 v/v, a reaction time of 1 minute, and a total gas flow of 80 NmL/min. In the sample obtained under the optimized conditions, 80% of the area was covered with monolayer graphene and less than 1% with multilayer graphene.

  19. Total Synthesis of Plakilactones C, B and des-Hydroxyplakilactone B by the Oxidative Cleavage of Gracilioether Furanylidenes.

    Science.gov (United States)

    Norris, Matthew D; Perkins, Michael V

    2016-08-01

    A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl4. PMID:27359169

  20. Reactivity umpolung in intramolecular ring closure of 3,4-disubstituted butenolides: diastereoselective total synthesis of paeonilide.

    Science.gov (United States)

    Deore, Prashant S; Argade, Narshinha P

    2013-11-15

    Remarkable reactivity reversal stratagem in 3,4-disubstituted butenolides under acidic conditions is described. Design of a suitably substituted multifunctional butenolide followed by an acid-catalyzed chemo- and diastereoselective intramolecular ring closure via the reactivity umpolung has been demonstrated to accomplish a concise total synthesis of paeonilide. Overall, the present protocol involves one-pot reduction of an α,β-unsaturated carbon-carbon double bond and intramolecular nucleophilic insertion of oxygen function at the electron-rich γ-position of butenolide. The involved mechanistic aspects have also been discussed. PMID:24175675

  1. Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf formosa. Isolation and Total Synthesis

    Directory of Open Access Journals (Sweden)

    Carmen Murcia

    2014-02-01

    Full Text Available Tanjungides A (1 (Z isomer and B (2 (E isomer, two novel dibrominated indole enamides, have been isolated from the tunicate Diazona cf formosa. Their structures were determined by spectroscopic methods including HRMS, and extensive 1D and 2D NMR. The stereochemistry of the cyclised cystine present in both compounds was determined by Marfey’s analysis after chemical degradation and hydrolysis. We also report the first total synthesis of these compounds using methyl 1H-indole-3-carboxylate as starting material and a linear sequence of 11 chemical steps. Tanjungides A and B exhibit significant cytotoxicity against human tumor cell lines.

  2. Tanjungides A and B: new antitumoral bromoindole derived compounds from Diazona cf formosa. isolation and total synthesis.

    Science.gov (United States)

    Murcia, Carmen; Coello, Laura; Fernández, Rogelio; Martín, María Jesús; Reyes, Fernando; Francesch, Andrés; Munt, Simon; Cuevas, Carmen

    2014-02-21

    Tanjungides A (1) (Z isomer) and B (2) (E isomer), two novel dibrominated indole enamides, have been isolated from the tunicate Diazona cf formosa. Their structures were determined by spectroscopic methods including HRMS, and extensive 1D and 2D NMR. The stereochemistry of the cyclised cystine present in both compounds was determined by Marfey's analysis after chemical degradation and hydrolysis. We also report the first total synthesis of these compounds using methyl 1H-indole-3-carboxylate as starting material and a linear sequence of 11 chemical steps. Tanjungides A and B exhibit significant cytotoxicity against human tumor cell lines.

  3. The first protein ever synthesized in vitro——a personal reminiscence of the total synthesis of crystalline insulin

    Institute of Scientific and Technical Information of China (English)

    ZHANG YouShang

    2010-01-01

    @@ The total synthesis of crystalline bovine insulin started in 1958 was fully accomplished in 1965.This formidable task was a collaboration of the Institute of Biochemistry in Shanghai, the Institute of Organic Chemistry in Shanghai and the Department of Chemistry in Beijing University.It is difficult to say exactly how many people were involved in this project, as many contributors, e.g.Director Wang YingLai and Deputy Director Cao TianQin of the Institute of Biochemistry, were not included in the author list of the published papers.

  4. Functional Biomimetic Architectures

    Science.gov (United States)

    Levine, Paul M.

    N-substituted glycine oligomers, or 'peptoids,' are a class of sequence--specific foldamers composed of tertiary amide linkages, engendering proteolytic stability and enhanced cellular permeability. Peptoids are notable for their facile synthesis, sequence diversity, and ability to fold into distinct secondary structures. In an effort to establish new functional peptoid architectures, we utilize the copper-catalyzed azide-alkyne [3+2] cycloaddition (CuAAC) reaction to generate peptidomimetic assemblies bearing bioactive ligands that specifically target and modulate Androgen Receptor (AR) activity, a major therapeutic target for prostate cancer. Additionally, we explore chemical ligation protocols to generate semi-synthetic hybrid biomacromolecules capable of exhibiting novel structures and functions not accessible to fully biosynthesized proteins.

  5. Enantioselective total synthesis of (−)-epoxyquinols A and B. Novel, convenient access to chiral epoxyquinone building blocks through enzymatic desymmetrization

    OpenAIRE

    Mehta, Goverdhan; Islam, Kabirul

    2004-01-01

    Following our recent total synthesis of the biologically potent natural products epoxyquinols A and B in racemic form, we have now accomplished the total synthesis of the (−)-epoxyquinols A and B, anti-podes of the angiogenesis inhibiting natural products, through a protocol that involves enzymatic desymmetrization of a versatile epoxyquinone derivative, readily available from the Diels–Alder adduct of cyclopentadiene and p-benzoquinone.

  6. The First Total Synthesis of 4,4′-Biisofraxidin

    Institute of Scientific and Technical Information of China (English)

    LEi,Jiang-Guang(雷建光); LIN,Gu-Qiang(林国强)

    2002-01-01

    The 4,4′- biisofraxidin, isolated from balsamina L. was synthesized for the first time in the total yield of 7% by 11 steps, in which the key step was the cyclization and Ni(0)- catalyzed coupling reaction.

  7. Total synthesis and biochemical evaluation of azumamides A–E and analogs

    DEFF Research Database (Denmark)

    Villadsen, Jesper

    structures. The key step in this route is a diastereoselective Mannich reaction, which enabled us to prepare two site-specifically edited epimeric azumamide analogs, where the stereochemistry in the unique -amino acid was inverted. The two epimeric homologs were screened together with azumamide A−E against...... the entire panel of recombinant HDAC isoforms. Thus, providing the first full profiling of the azumamides. The epimers were inactive against the full panel of HDAC enzymes and show that the -amino acid scaffold is highly sensitive to modifications in the stereochemistry. The profiling of the natural products...... analogs. Having observed the importance of the aromatic amino acid in the azumamides, a tryptophan-series was also prepared. The synthesis of these compounds underline the broad perspective and flexibility of the developed Mannich strategy. The dimethylated analogs were found to be poor HDAC inhibitors...

  8. Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

    Directory of Open Access Journals (Sweden)

    Jens Schmidt

    2014-05-01

    Full Text Available The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423 in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

  9. Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursors.

    Science.gov (United States)

    Fang, Hsin Wei; Liao, Yu-Ren; Hwang, Tsong-Long; Shieh, Po-Chuen; Lee, Kuo-Hsiung; Hung, Hsin-Yi; Wu, Tian-Shung

    2015-09-15

    In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC50 4.87 μg/mL) and elastase release (IC50 6.29 μg/mL). PMID:26248804

  10. Biomimetic implant coatings.

    Science.gov (United States)

    Eisenbarth, E; Velten, D; Breme, J

    2007-02-01

    Biomaterials and tissue engineering technologies are becoming increasingly important in biomedical practice, particularly as the population ages. Cellular responses depend on topographical properties of the biomaterial at the nanometer scale. Structures on biomaterial surfaces are used as powerful tools to influence or even control interactions between implants and the biological system [; ]. The influence of nanometer sized surface structures on osteoblastlike cell interactions was tested with niobium oxide coatings on polished titanium slices (cp-Ti grade 2). The aim of the study was to investigate the influence of nanoscopic surface structures on osteoblast interactions in order to support collagen I production and cell adhesion. The coatings were done by means of the sol-gel process. The surface structure was adjusted by annealing of the metaloxide ceramic coatings due to temperature depended crystal growth. The applied annealing temperatures were 450, 550 and 700 degrees C for 1 h, corresponding to Ra-numbers of 7, 15 and 40 nm. The surfaces were characterized by means of AFM, DTA/TG, diffractometry and white light interferometry. The cell reactions were investigated concerning adhesion kinetics, migration, spreading, cell adhesion, and collagen I synthesis. The smooth surface (Ra=7 nm) resulted in the fastest cell anchorage and cell migration. The closest cell adhesion was reached with the surface structure of Ra=15 nm. The roughest surface (Ra=40 nm) impedes the cell migration as well as a proper spreading of the cells. The best results concerning cell adhesion and spreading was reached with an intermediate surface roughness of Ra=15 nm of the niobium oxide coating on cp-titanium slices. PMID:16828342

  11. Biomimetic microenvironments for regenerative endodontics.

    Science.gov (United States)

    Kaushik, Sagar N; Kim, Bogeun; Walma, Alexander M Cruz; Choi, Sung Chul; Wu, Hui; Mao, Jeremy J; Jun, Ho-Wook; Cheon, Kyounga

    2016-01-01

    Regenerative endodontics has been proposed to replace damaged and underdeveloped tooth structures with normal pulp-dentin tissue by providing a natural extracellular matrix (ECM) mimicking environment; stem cells, signaling molecules, and scaffolds. In addition, clinical success of the regenerative endodontic treatments can be evidenced by absence of signs and symptoms; no bony pathology, a disinfected pulp, and the maturation of root dentin in length and thickness. In spite of the various approaches of regenerative endodontics, there are several major challenges that remain to be improved: a) the endodontic root canal is a strong harbor of the endodontic bacterial biofilm and the fundamental etiologic factors of recurrent endodontic diseases, (b) tooth discolorations are caused by antibiotics and filling materials, (c) cervical root fractures are caused by endodontic medicaments, (d) pulp tissue is not vascularized nor innervated, and (e) the dentin matrix is not developed with adequate root thickness and length. Generally, current clinical protocols and recent studies have shown a limited success of the pulp-dentin tissue regeneration. Throughout the various approaches, the construction of biomimetic microenvironments of pulp-dentin tissue is a key concept of the tissue engineering based regenerative endodontics. The biomimetic microenvironments are composed of a synthetic nano-scaled polymeric fiber structure that mimics native pulp ECM and functions as a scaffold of the pulp-dentin tissue complex. They will provide a framework of the pulp ECM, can deliver selective bioactive molecules, and may recruit pluripotent stem cells from the vicinity of the pulp apex. The polymeric nanofibers are produced by methods of self-assembly, electrospinning, and phase separation. In order to be applied to biomedical use, the polymeric nanofibers require biocompatibility, stability, and biodegradability. Therefore, this review focuses on the development and application of the

  12. Biomimetic microenvironments for regenerative endodontics.

    Science.gov (United States)

    Kaushik, Sagar N; Kim, Bogeun; Walma, Alexander M Cruz; Choi, Sung Chul; Wu, Hui; Mao, Jeremy J; Jun, Ho-Wook; Cheon, Kyounga

    2016-01-01

    Regenerative endodontics has been proposed to replace damaged and underdeveloped tooth structures with normal pulp-dentin tissue by providing a natural extracellular matrix (ECM) mimicking environment; stem cells, signaling molecules, and scaffolds. In addition, clinical success of the regenerative endodontic treatments can be evidenced by absence of signs and symptoms; no bony pathology, a disinfected pulp, and the maturation of root dentin in length and thickness. In spite of the various approaches of regenerative endodontics, there are several major challenges that remain to be improved: a) the endodontic root canal is a strong harbor of the endodontic bacterial biofilm and the fundamental etiologic factors of recurrent endodontic diseases, (b) tooth discolorations are caused by antibiotics and filling materials, (c) cervical root fractures are caused by endodontic medicaments, (d) pulp tissue is not vascularized nor innervated, and (e) the dentin matrix is not developed with adequate root thickness and length. Generally, current clinical protocols and recent studies have shown a limited success of the pulp-dentin tissue regeneration. Throughout the various approaches, the construction of biomimetic microenvironments of pulp-dentin tissue is a key concept of the tissue engineering based regenerative endodontics. The biomimetic microenvironments are composed of a synthetic nano-scaled polymeric fiber structure that mimics native pulp ECM and functions as a scaffold of the pulp-dentin tissue complex. They will provide a framework of the pulp ECM, can deliver selective bioactive molecules, and may recruit pluripotent stem cells from the vicinity of the pulp apex. The polymeric nanofibers are produced by methods of self-assembly, electrospinning, and phase separation. In order to be applied to biomedical use, the polymeric nanofibers require biocompatibility, stability, and biodegradability. Therefore, this review focuses on the development and application of the

  13. Total Synthesis of Trimethoprim%甲氧苄啶的全合成

    Institute of Scientific and Technical Information of China (English)

    冀亚飞; 李前荣

    2001-01-01

    对甲酚为起始原料,以总收率40.6%的高收率合成了杀菌增效剂甲氧苄啶.对 甲酚进行溴化、水解反应得到4-羟基-3,5-二溴苯甲醛;该化合物以甲醇钠甲醇溶液 进行甲氧基化反应获得4-羟基-3,5-二甲氧基苯甲醛的酚钠盐,然后直接以硫酸二甲 酯进行甲基化反应得到3,4,5-三甲氧基苯甲醛;用其通过与甲醇钠、丙烯氰的甲醇溶 液反应得到肉桂氰衍生物;该衍生物先经碱催化的1,3-质子转移异构化到烯醚结构, 再与甲醇加成,直接与胍缩合环化,最终得到甲氧苄啶.%Antibacterial synergist trimethoprim was synthesized from p-cresol in an overall yield as high as 40. 6%. p-cresol was brominated and hydrolyzed to give 3, 5-dibromo-4-hydroxyben- zaldehyde, which was methoxylated by methanolic sodium methoxide associated with cuprous chloride and dimethyfformamide(DMF)as catalyst at 125℃ (ca. 0.SMPa)to provide sodium phenolate of 3,5- dimethoxy-4-hydroxybenzaldehyde, from which 3,4,5-trimethoxybenzaldehyde was obtained by methy lation directly with dimethylsuffate in aqueous sodium hydroxide. Efficient synthesis of trimethoprim from 3,4,5-trimethoxybenzaldehyde was accomplished by condensation with methanolic sodium methox ide, methanol and acrylonitrile via prior base-catalyzed 1,3-prototropic isomerization of cinnamonitrile converted into the enol ether, followed by addition with methanol at 90℃ (ca. 0.05MPa)and cyclo condensation directly with guanidine in dimethyl sulfoxide(DMSO)at 110℃ with the removal of methanol. "One-pot" method was used in the synthesis starting from economical, convenient and envi ronmental awareness.

  14. Monitoring the catalytic synthesis of glycerol carbonate by real-time attenuated total reflection FTIR spectroscopy

    NARCIS (Netherlands)

    Calvino-Casilda, V.; Mul, G.; Fernandez, J.F.; Rubio-Marcos, F.; Banares, M.A.

    2011-01-01

    In situ Attenuated Total Reflectance FTIR spectroscopy was used to study the carbonylation of glycerol with urea. Cobalt oxide nanoparticles, Co3O4, hierarchically dispersed on zinc oxide microparticles, ZnO, were used as catalysts. The present work demonstrates that in situ real-time attenuated tot

  15. Biomimetic Nanotubes Based on Cyclodextrins for Ion-Channel Applications.

    Science.gov (United States)

    Mamad-Hemouch, Hajar; Ramoul, Hassen; Abou Taha, Mohammad; Bacri, Laurent; Huin, Cécile; Przybylski, Cédric; Oukhaled, Abdelghani; Thiébot, Bénédicte; Patriarche, Gilles; Jarroux, Nathalie; Pelta, Juan

    2015-11-11

    Biomimetic membrane channels offer a great potential for fundamental studies and applications. Here, we report the fabrication and characterization of short cyclodextrin nanotubes, their insertion into membranes, and cytotoxicity assay. Mass spectrometry and high-resolution transmission electron microscopy were used to confirm the synthesis pathway leading to the formation of short nanotubes and to describe their structural parameters in terms of length, diameter, and number of cyclodextrins. Our results show the control of the number of cyclodextrins threaded on the polyrotaxane leading to nanotube synthesis. Structural parameters obtained by electron microscopy are consistent with the distribution of the number of cyclodextrins evaluated by mass spectrometry from the initial polymer distribution. An electrophysiological study at single molecule level demonstrates the ion channel formation into lipid bilayers, and the energy penalty for the entry of ions into the confined nanotube. In the presence of nanotubes, the cell physiology is not altered.

  16. Sol–gel auto-combustion synthesis of totally immiscible NiAg alloy

    International Nuclear Information System (INIS)

    Highlights: ► Chemically synthesized immiscible NiAg alloy nanoparticles without protecting matrix. ► A chemical method providing both a nonequilibrium thermal process and a good mixing of precursors. ► Observation of extinction planes in NiAg alloy. -- Abstract: Immiscible crystalline NiAg alloy was successfully synthesized by the newly developed sol–gel auto-combustion method. The structure and composition were examined by X-ray diffraction (XRD) and high resolution transmission electron microscope (HRTEM). All evidence supports that homogeneous NiAg alloy with FCC structure was synthesized. The differential thermal analysis and thermogravimetry (DTA–TG) measurement shows that the alloy has a good thermal stability until 315 °C. Unusually some extinction planes are observed in the XRD pattern and HRTEM images. The random distribution of atoms and the large difference between Ni and Ag atom form factors should be regarded as the main reasons for the observation of the extinction planes. The quenching like nonequilibrium thermal process in the combustion is taken as the key factor in the synthesis of immiscible alloy. And the addition of ethylene glycol in the precursors is found to benefit the formation of NiAg alloy.

  17. First Total Synthesis of Hyacinthacine A6 from the Protected Derivative of Polyhydroxylated Pyrrolidine

    Institute of Scientific and Technical Information of China (English)

    ZHANG Tao-xiang; ZHOU Ling; AO Xiao-ping

    2008-01-01

    (1S,2R,3R,5R,7aR)-1,2-Dihydroxy-3-hydroxymethy1-5-methylpyrrolizidine(hyacinthacine A6,1) was synthesized by Wittig's methodology via the reaction of aldehyde 6,prepared from the partially protected derivative of polyhydroxylatcd pyrrolidine,with appropriated ylides,followed by cyclization through the internal reductive amination process of the resulting a,β-unsaturated ketone 7,and total deprotection.

  18. Synthesis,Charactcrization and Antibacterial Property of Strontium Half and Totally Substituted Hydroxyapatite Nanoparticles

    Institute of Scientific and Technical Information of China (English)

    LIN Yingguang; YANG Zhuoru; CHENG Jiang; WANG Lianshi

    2008-01-01

    Nanoparticles of hydroxyapatite(HAP),strontium half substituted hydroxyapatite(SrCaHAP) and strontium totally substituted hydroxyapatite(SrHAP)were prepared by sol-gel-supercritical fluid drying (SCFD) method.The nanoparticles were characterized by element content analysis,FT-IR,XRD and TEM,and the effects of strontium substitution on crystal structure.crystallinity,particle shape and antibacterial propemes of the nanoparticles on Escherichia coli,Staphylococcus aureus,Lactobacillus were researched.Results show that strontium can half and totally substitute for calcium and enter the structure of apatite according to the initial atomic ratios of Sr/[Sr+Ca] as 0.5,1.The substitution decreases the IR wavenumbers of SrCaHAP and SrHAP, and changes the morphology of the nanoparticles from short rod shaped HAP to needle shaped SrCaHAE and back to short rod shaped SrHAP.The crystallinity of HAP is higher than that of SrCaHAP, but is lower thall that of SrHAP.Moreove~the antibacterial property of SrCaHAP and SrHAP are improved after the calcium is half and totally substituted by strontium.

  19. Researches and developments of biomimetics in tribology

    Institute of Scientific and Technical Information of China (English)

    DAI Zhendong; TONG Jin; REN Luquan

    2006-01-01

    Animals and plants have developed optimal geometric structures, smart topological materials and multi-functional surface textures with excellent tribological characteristics through the evolution of thousand millions of years and become models for tribological design. This paper puts forward the definition and fundament of biomimetic tribology, investigates the status of self-cleaning of liquid-solid interface, adhesion between animals' feet and solid surface, wear characteristics of biological surfaces and biomimetic design, as well as the friction and bionic design on liquid-solid interface. The further developments of the tribological biomimetics are discussed.

  20. Challenges in Commercializing Biomimetic Membranes

    Directory of Open Access Journals (Sweden)

    Mark Perry

    2015-11-01

    Full Text Available The discovery of selective water channel proteins—aquaporins—has prompted growing interest in using these proteins, as the building blocks for designing new types of membranes. However, as with any other new and potentially disruptive technology, barriers for successful market entry exist. One category includes customer-related barriers, which can be influenced to some extent. Another category includes market-technical-related barriers, which can be very difficult to overcome by an organization/company aiming at successfully introducing their innovation on the market—in particular if both the organization and the technology are at early stages. Often, one faces barriers from both these categories at the same time, which makes it necessary to gain insight of the particular market when introducing a new innovative product. In this review we present the basic concepts and discuss some of these barriers and challenges associated with introducing biomimetic aquaporin membranes. These include technical issues in membrane production and product testing. Then we discuss possible business models for introducing new technologies in general, followed by a presentation of beach-head market segments relevant for biomimetic aquaporin membranes.

  1. Efficient Total Chemical Synthesis of (13) C=(18) O Isotopomers of Human Insulin for Isotope-Edited FTIR.

    Science.gov (United States)

    Dhayalan, Balamurugan; Fitzpatrick, Ann; Mandal, Kalyaneswar; Whittaker, Jonathan; Weiss, Michael A; Tokmakoff, Andrei; Kent, Stephen B H

    2016-03-01

    Isotope-edited two-dimensional Fourier transform infrared spectroscopy (2 D FTIR) can potentially provide a unique probe of protein structure and dynamics. However, general methods for the site-specific incorporation of stable (13) C=(18) O labels into the polypeptide backbone of the protein molecule have not yet been established. Here we describe, as a prototype for the incorporation of specific arrays of isotope labels, the total chemical synthesis-via a key ester insulin intermediate-of 97 % enriched [(1-(13) C=(18) O)Phe(B24) ] human insulin: stable-isotope labeled at a single backbone amide carbonyl. The amino acid sequence as well as the positions of the disulfide bonds and the correctly folded structure were unambiguously confirmed by the X-ray crystal structure of the synthetic protein molecule. In vitro assays of the isotope labeled [(1-(13) C=(18) O)Phe(B24) ] human insulin showed that it had full insulin receptor binding activity. Linear and 2 D IR spectra revealed a distinct red-shifted amide I carbonyl band peak at 1595 cm(-1) resulting from the (1-(13) C=(18) O)Phe(B24) backbone label. This work illustrates the utility of chemical synthesis to enable the application of advanced physical methods for the elucidation of the molecular basis of protein function. PMID:26715336

  2. Extending the Glucosyl Ceramide Cassette Approach: Application in the Total Synthesis of Ganglioside GalNAc-GM1b

    Directory of Open Access Journals (Sweden)

    Miku Konishi

    2013-12-01

    Full Text Available The development of a novel cyclic glucosyl ceramide cassette acceptor for efficient glycolipid syntheses was investigated. p-Methoxybenzyl (PMB groups were selected as protecting groups at C2 and C3 of the glucose residue with the aim of improving the functionality of the cassette acceptor. The choice of the PMB group resulted in a loss of β-selectivity, which was corrected by using an appropriate tether to control the spatial arrangement and the nitrile solvent effect. To investigate the effect of linker structure on the β-selectivity of intramolecular glycosylation, several linkers for tethering the glucose and ceramide moiety were designed and prepared, namely, succinyl, glutaryl, dimethylmalonyl, and phthaloyl esters. The succinyl ester linker was the best for accessing the cassette form. The newly designed glucosyl ceramide cassette acceptor was then applied in the total synthesis of ganglioside GalNAc-GM1b.

  3. Isolation and Total Synthesis of Stolonines A-C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera.

    Science.gov (United States)

    Tran, Trong D; Pham, Ngoc B; Ekins, Merrick; Hooper, John N A; Quinn, Ronald J

    2015-07-01

    Cnemidocarpa stolonifera is an underexplored marine tunicate that only occurs on the tropical to subtropical East Coast of Australia, with only two pyridoacridine compounds reported previously. Qualitative analysis of the lead-like enhanced fractions of C. stolonifera by LC-MS dual electrospray ionization coupled with PDA and ELSD detectors led to the identification of three new natural products, stolonines A-C (1-3), belonging to the taurine amide structure class. Structures of the new compounds were determined by NMR and MS analyses and later verified by total synthesis. This is the first time that the conjugates of taurine with 3-indoleglyoxylic acid, quinoline-2-carboxylic acid and β-carboline-3-carboxylic acid present in stolonines A-C (1-3), respectively, have been reported. An immunofluorescence assay on PC3 cells indicated that compounds 1 and 3 increased cell size, induced mitochondrial texture elongation, and caused apoptosis in PC3 cells. PMID:26204949

  4. Isolation and Total Synthesis of Stolonines A-C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera.

    Science.gov (United States)

    Tran, Trong D; Pham, Ngoc B; Ekins, Merrick; Hooper, John N A; Quinn, Ronald J

    2015-07-22

    Cnemidocarpa stolonifera is an underexplored marine tunicate that only occurs on the tropical to subtropical East Coast of Australia, with only two pyridoacridine compounds reported previously. Qualitative analysis of the lead-like enhanced fractions of C. stolonifera by LC-MS dual electrospray ionization coupled with PDA and ELSD detectors led to the identification of three new natural products, stolonines A-C (1-3), belonging to the taurine amide structure class. Structures of the new compounds were determined by NMR and MS analyses and later verified by total synthesis. This is the first time that the conjugates of taurine with 3-indoleglyoxylic acid, quinoline-2-carboxylic acid and β-carboline-3-carboxylic acid present in stolonines A-C (1-3), respectively, have been reported. An immunofluorescence assay on PC3 cells indicated that compounds 1 and 3 increased cell size, induced mitochondrial texture elongation, and caused apoptosis in PC3 cells.

  5. Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera

    Directory of Open Access Journals (Sweden)

    Trong D. Tran

    2015-07-01

    Full Text Available Cnemidocarpa stolonifera is an underexplored marine tunicate that only occurs on the tropical to subtropical East Coast of Australia, with only two pyridoacridine compounds reported previously. Qualitative analysis of the lead-like enhanced fractions of C. stolonifera by LC-MS dual electrospray ionization coupled with PDA and ELSD detectors led to the identification of three new natural products, stolonines A–C (1–3, belonging to the taurine amide structure class. Structures of the new compounds were determined by NMR and MS analyses and later verified by total synthesis. This is the first time that the conjugates of taurine with 3-indoleglyoxylic acid, quinoline-2-carboxylic acid and β-carboline-3-carboxylic acid present in stolonines A–C (1–3, respectively, have been reported. An immunofluorescence assay on PC3 cells indicated that compounds 1 and 3 increased cell size, induced mitochondrial texture elongation, and caused apoptosis in PC3 cells.

  6. Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua.

    Science.gov (United States)

    Tanabe, Genzoh; Sugano, Youta; Shirato, Miki; Sonoda, Naoki; Tsutsui, Nozomi; Morikawa, Toshio; Ninomiya, Kiyofumi; Yoshikawa, Masayuki; Muraoka, Osamu

    2015-07-24

    The first total synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an α,α-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported (13)C NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 μM) of 6 was 40 times stronger than that of arbutin (174 μM), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor within this class of compounds. PMID:26135746

  7. Total Synthesis of Purported Cephalosporolides H and I, Penisporolide B, and Their Stereoisomers.

    Science.gov (United States)

    Wang, Jian; Tong, Rongbiao

    2016-05-20

    Development of a unified, bioinspired synthetic strategy to access four possible diastereomers of unique 2,2-dimethyl-[5,5]-spiroacetal-cis-fused-γ-lactone (Me2SAFL) is reported, featuring pyridinium chlorochromate (PCC)-promoted oxidative ring expansion of β-hydroxy cyclic ethers and dehydrative ring-contraction rearrangement of 10-membered lactones. Synthetic utility of this strategy was demonstrated by total syntheses of 12 Me2SAFLs, corresponding to the purported cephalosporolide H (CesH), cephalosporolide I (CesI), and penisporolide B (PenB) and their possible diastereomers. Comprehensive NMR data analysis suggested that the tricyclic Me2SAFL core of CesH, CesI, and PenB should be revised to the same relative (3R*, 4R*, 6S*, 9R*) configuration and that the side chains required an unknown constitutional structure revision. PMID:27137949

  8. Total Observed Organic Carbon (TOOC): A Synthesis of North American Observations

    Science.gov (United States)

    Heald, C. L.; Goldstein, A. H.; Allan, J. D.; Aiken, A. C.; Apel, E.; Atlas, E. L.; Baker, A. K.; Bates, T. S.; Beyersdorf, A. J.; Blake, D. R.; Campos, T.; Coe, H.; Crounse, J. D.; DeCarlo, P. F.; de Gouw, J. A.; Dunlea, E. J.; Flocke, F. M.; Fried, A.; Goldan, P.; Griffin, R. J.; Herndon, S. C.; Holloway, J. S.; Holzinger, R.; Jimenez, J. L.; Junkermann, W.

    2007-01-01

    Measurements of organic carbon compounds in both the gas and particle phases made upwind, over and downwind of North America are synthesized to examine the total observed organic carbon (TOOC) in the atmosphere over this region. These include measurements made aboard the NOAA WP-3 and BAe-146 aircraft, the NOAA research vessel Ronald H. Brown, and at the Thompson Farm and Chebogue Point surface sites during the summer 2004 ICARTT campaign. Both winter and summer 2002 measurements during the Pittsburgh Air Quality Study are also included. Lastly, the spring 2002 observations at Trinidad Head, CA, surface measurements made in March 2006 in Mexico City and coincidentally aboard the C-130 aircraft during the MILAGRO campaign and later during the IMPEX campaign off the northwestern United States are incorporated. Concentrations of TOOC in these datasets span more than two orders of magnitude. The daytime mean TOOC ranges from 4.0 to 456 microg C/cubic m from the cleanest site (Trinidad Head) to the most polluted (Mexico City). Organic aerosol makes up 3-17% of this mean TOOC, with highest fractions reported over the northeastern United States, where organic aerosol can comprise up to 50% of TOOC. Carbon monoxide concentrations explain 46 to 86% of the variability in TOOC, with highest TOOC/CO slopes in regions with fresh anthropogenic influence, where we also expect the highest degree of mass closure for TOOC. Correlation with isoprene, formaldehyde, methyl vinyl ketone and methacrolein also indicates that biogenic activity contributes substantially to the variability of TOOC, yet these tracers of biogenic oxidation sources do not explain the variability in organic aerosol observed over North America. We highlight the critical need to develop measurement techniques to routinely detect total gas phase VOCs, and to deploy comprehensive suites of TOOC instruments in diverse environments to quantify the ambient evolution of organic carbon from source to sink.

  9. Total observed organic carbon (TOOC in the atmosphere: a synthesis of North American observations

    Directory of Open Access Journals (Sweden)

    C. L. Heald

    2008-04-01

    Full Text Available Measurements of organic carbon compounds in both the gas and particle phases made upwind, over and downwind of North America are synthesized to examine the total observed organic carbon (TOOC in the atmosphere over this region. These include measurements made aboard the NOAA WP-3 and BAe-146 aircraft, the NOAA research vessel Ronald H. Brown, and at the Thompson Farm and Chebogue Point surface sites during the summer 2004 ICARTT campaign. Both winter and summer 2002 measurements during the Pittsburgh Air Quality Study are also included. Lastly, the spring 2002 observations at Trinidad Head, CA, surface measurements made in March 2006 in Mexico City and coincidentally aboard the C-130 aircraft during the MILAGRO campaign and later during the IMPEX campaign off the northwestern United States are incorporated. Concentrations of TOOC in these datasets span more than two orders of magnitude. The daytime mean TOOC ranges from 4.0 to 456 μgC m−3 from the cleanest site (Trinidad Head to the most polluted (Mexico City. Organic aerosol makes up 3–17% of this mean TOOC, with highest fractions reported over the northeastern United States, where organic aerosol can comprise up to 50% of TOOC. Carbon monoxide concentrations explain 46 to 86% of the variability in TOOC, with highest TOOC/CO slopes in regions with fresh anthropogenic influence, where we also expect the highest degree of mass closure for TOOC. Correlation with isoprene, formaldehyde, methyl vinyl ketone and methacrolein also indicates that biogenic activity contributes substantially to the variability of TOOC, yet these tracers of biogenic oxidation sources do not explain the variability in organic aerosol observed over North America. We highlight the critical need to develop measurement techniques to routinely detect total gas phase VOCs, and to deploy comprehensive suites of TOOC instruments in diverse environments to quantify the ambient evolution of organic carbon from source

  10. Total Observed Organic Carbon (TOOC: A synthesis of North American observations

    Directory of Open Access Journals (Sweden)

    C. L. Heald

    2007-12-01

    Full Text Available Measurements of organic carbon compounds in both the gas and particle phases measured upwind, over and downwind of North America are synthesized to examine the total observed organic carbon (TOOC over this region. These include measurements made aboard the NOAA WP-3 and BAe-146 aircraft, the NOAA research vessel Ronald H. Brown, and at the Thompson Farm and Chebogue Point surface sites during the summer 2004 ICARTT campaign. Both winter and summer 2002 measurements during the Pittsburgh Air Quality Study are also included. Lastly, the spring 2002 observations at Trinidad Head, CA, surface measurements made in March 2006 in Mexico City and coincidentally aboard the C-130 aircraft during the MILAGRO campaign and later during the IMPEX campaign off the northwestern United States are incorporated. Concentrations of TOOC in these datasets span more than two orders of magnitude. The daytime mean TOOC ranges from 4.0 to 456 μgC m−3 from the cleanest site (Trinidad Head to the most polluted (Mexico City. Organic aerosol makes up 3–17% of this mean TOOC, with highest fractions reported over the northeastern United States, where organic aerosol can comprise up to 50% of TOOC. Carbon monoxide concentrations explain 46 to 86% of the variability in TOOC, with highest TOOC/CO slopes in regions with fresh anthropogenic influence, where we also expect the highest degree of mass closure for TOOC. Correlation with isoprene, formaldehyde, methyl vinyl ketene and methacrolein also indicates that biogenic activity contributes substantially to the variability of TOOC, yet these tracers of biogenic oxidation sources do not explain the variability in organic aerosol observed over North America. We highlight the critical need to develop measurement techniques to routinely detect total gas phase VOCs, and to deploy comprehensive suites of TOOC instruments in diverse environments to quantify the ambient evolution of organic carbon from source to sink.

  11. Molecular motor assembly of a biomimetic system

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    @@ Active biological molecules and functional structures can be fabricated into a bio-mimetic system by using molecular assembly method. Such materials can be used for the drug delivery, disease diagnosis and therapy, and new nanodevice construction.

  12. Biomimetic catalysis: Taking on the turnover challenge

    Science.gov (United States)

    Hooley, Richard J.

    2016-03-01

    Emulating the efficiency with which enzymes catalyse reactions has often been used as inspiration to develop self-assembled cages. Now two studies present approaches to achieving catalyst turnover -- one of the biggest challenges in achieving truly biomimetic catalysis.

  13. Biomimetic membranes for sensor and separation applications

    CERN Document Server

    2012-01-01

    This book addresses the possibilities and challenges in mimicking biological membranes and creating membrane-based sensor and separation devices. It covers recent advances in developing biomimetic membranes for technological applications with a focus on the use of integral membrane protein mediated transport. It describes the fundamentals of biosensing as well as separation and shows how the two processes work together in biological systems. The book provides an overview of the current state of the art, points to areas that need further investigation and anticipates future directions in the field. Biomimetics is a truly cross-disciplinary approach and this is exemplified by the challenges in mimicking osmotic processes as they occur in nature using aquaporin protein water channels as central building blocks. In the development of a biomimetic sensor/separation technology, both channel and carrier proteins are important and examples of how these may be reconstituted and controlled in biomimetic membranes are ...

  14. Solid state NMR method development and studies of biological and biomimetic nanocomposites

    Energy Technology Data Exchange (ETDEWEB)

    Hu, Yanyan

    2011-02-07

    This thesis describes application and development of advanced solid-state nuclear magnetic resonance techniques for complex materials, in particular organic-inorganic nanocomposites and thermoelectric tellurides. The apatite-collagen interface, essential for understanding the biomineralization process in bone and engineering the interface for controlled bio-mimetic synthesis and optimized mechanical properties, is buried within the nanocomposite of bone. We used multinuclear solid-state NMR to study the composition and structure of the interface. Citrate has been identified as the main organic molecule strongly bound to the apatite surface with a density of 1/(2 nm){sup 2}, covering 1/6 of the total surface area in bovine bone. Citrate provides more carboxylate groups, one of the key functional groups found to affect apatite nucleation and growth, than all the non-collagenous proteins all together in bone; thus we propose that citrate stabilizes apatite crystals at a very small thickness of {approx}3 nm (4 unit cells) to increase bone fracture tolerance. The hypothesis has been confirmed in vitro by adding citrate in the bio-mimetic synthesis of polymerhydroxyapatite nanocomposites. The results have shown that the size of hydroxyapatite nanocrystals decreases as increasing citrate concentration. With citrate concentrations comparable to that in body fluids, similar-sized nanocrystals as in bone have been produced. Besides the dimensions of the apatite crystals, the composition of bone also affects its biofunctional and macroscopic mechanical properties; therefore, our team also extended its effort to enhance the inorganic portion in our bio-mimetic synthesis from originally 15 wt% to current 50 wt% compared to 65 wt% in bovine bone, by using Lysine-Leucine hydroxyapatite nucleating diblock co-polypeptide, which forms a gel at very low concentration. In this thesis, various advanced solid state NMR techniques have been employed to characterize nanocomposites

  15. Solid state NMR method development and studies of biological and biomimetic nanocomposites

    Energy Technology Data Exchange (ETDEWEB)

    Hu, Yanyan [Iowa State Univ., Ames, IA (United States)

    2011-01-01

    This thesis describes application and development of advanced solid-state nuclear magnetic resonance techniques for complex materials, in particular organic-inorganic nanocomposites and thermoelectric tellurides. The apatite-collagen interface, essential for understanding the biomineralization process in bone and engineering the interface for controlled bio-mimetic synthesis and optimized mechanical properties, is buried within the nanocomposite of bone. We used multinuclear solid-state NMR to study the composition and structure of the interface. Citrate has been identified as the main organic molecule strongly bound to the apatite surface with a density of 1/(2 nm)2, covering 1/6 of the total surface area in bovine bone. Citrate provides more carboxylate groups, one of the key functional groups found to affect apatite nucleation and growth, than all the non-collagenous proteins all together in bone; thus we propose that citrate stabilizes apatite crystals at a very small thickness of ~3 nm (4 unit cells) to increase bone fracture tolerance. The hypothesis has been confirmed in vitro by adding citrate in the bio-mimetic synthesis of polymerhydroxyapatite nanocomposites. The results have shown that the size of hydroxyapatite nanocrystals decreases as increasing citrate concentration. With citrate concentrations comparable to that in body fluids, similar-sized nanocrystals as in bone have been produced. Besides the dimensions of the apatite crystals, the composition of bone also affects its biofunctional and macroscopic mechanical properties; therefore, our team also extended its effort to enhance the inorganic portion in our bio-mimetic synthesis from originally 15 wt% to current 50 wt% compared to 65 wt% in bovine bone, by using Lysine-Leucine hydroxyapatite nucleating diblock co-polypeptide, which forms a gel at very low concentration. In this thesis, various advanced solid state NMR techniques have been employed to characterize nanocomposites

  16. Biomimetic Active Touch with Fingertips and Whiskers.

    Science.gov (United States)

    Lepora, Nathan F

    2016-01-01

    This study provides a synthetic viewpoint that compares, contrasts, and draws commonalities for biomimetic perception over a range of tactile sensors and tactile stimuli. Biomimetic active perception is formulated from three principles: (i) evidence accumulation based on leading models of perceptual decision making; (ii) action selection with an evidence-based policy, here based on overt focal attention; and (iii) sensory encoding of evidence based on neural coding. Two experiments with each of three biomimetic tactile sensors are considered: the iCub (capacitive) fingertip, the TacTip (optical) tactile sensor, and BIOTACT whiskers. For each sensor, one experiment considers a similar task (perception of shape and location) and the other a different tactile perception task. In all experiments, active perception with a biomimetic action selection policy based on focal attention outperforms passive perception with static or random action selection. The active perception also consistently reaches superresolved accuracy (hyperacuity) finer than the spacing between tactile elements. Biomimetic active touch thus offers a common approach for biomimetic tactile sensors to accurately and robustly characterize and explore non-trivial, uncertain environments analogous to how animals perceive the natural world. PMID:27168603

  17. Biomimetic mechanism for micro aircraft

    Science.gov (United States)

    Pines, Darryll J. (Inventor); Bohorquez, Felipe A. (Inventor); Sirohi, Jayant (Inventor)

    2005-01-01

    A biomimetic pitching and flapping mechanism including a support member, at least two blade joints for holding blades and operatively connected to the support member. An outer shaft member is concentric with the support member, and an inner shaft member is concentric with the outer shaft member. The mechanism allows the blades of a small-scale rotor to be actuated in the flap and pitch degrees of freedom. The pitching and the flapping are completely independent from and uncoupled to each other. As such, the rotor can independently flap, or independently pitch, or flap and pitch simultaneously with different amplitudes and/or frequencies. The mechanism can also be used in a non-rotary wing configuration, such as an ornithopter, in which case the rotational degree of freedom would be suppressed.

  18. Challenges in commercializing biomimetic membranes

    DEFF Research Database (Denmark)

    Perry, Mark; Madsen, Steen Ulrik; Jørgensen, Tine Elkjær;

    2015-01-01

    The discovery of selective water channel proteins—aquaporins—has prompted growing interest in using these proteins, as the building blocks for designing new types of membranes. However, as with any other new and potentially disruptive technology, barriers for successful market entry exist. One...... barriers and challenges associated with introducing biomimetic aquaporin membranes. These include technical issues in membrane production and product testing. Then we discuss possible business models for introducing new technologies in general, followed by a presentation of beach-head market segments...... organization and the technology are at early stages. Often, one faces barriers from both these categories at the same time, which makes it necessary to gain insight of the particular market when introducing a new innovative product. In this review we present the basic concepts and discuss some of these...

  19. Biomimetic use of genetic algorithms

    CERN Document Server

    Dessalles, Jean-Louis

    2011-01-01

    Genetic algorithms are considered as an original way to solve problems, probably because of their generality and of their "blind" nature. But GAs are also unusual since the features of many implementations (among all that could be thought of) are principally led by the biological metaphor, while efficiency measurements intervene only afterwards. We propose here to examine the relevance of these biomimetic aspects, by pointing out some fundamental similarities and divergences between GAs and the genome of living beings shaped by natural selection. One of the main differences comes from the fact that GAs rely principally on the so-called implicit parallelism, while giving to the mutation/selection mechanism the second role. Such differences could suggest new ways of employing GAs on complex problems, using complex codings and starting from nearly homogeneous populations.

  20. Biomimetic processing of oriented crystalline ceramic layers

    Energy Technology Data Exchange (ETDEWEB)

    Cesarano, J.; Shelnutt, J.A.

    1997-10-01

    The aim of this project was to develop the capabilities for Sandia to fabricate self assembled Langmuir-Blodgett (LB) films of various materials and to exploit their two-dimensional crystalline structure to promote the growth of oriented thin films of inorganic materials at room temperature. This includes the design and synthesis of Langmuir-active (amphiphilic) organic molecules with end groups offering high nucleation potential for various ceramics. A longer range goal is that of understanding the underlying principles, making it feasible to use the techniques presented in this report to fabricate unique oriented films of various materials for electronic, sensor, and membrane applications. Therefore, whenever possible, work completed in this report was completed with the intention of addressing the fundamental phenomena underlying the growth of crystalline, inorganic films on template layers of highly organized organic molecules. This problem was inspired by biological processes, which often produce exquisitely engineered structures via templated growth on polymeric layers. Seashells, for example, exhibit great toughness owing to their fine brick-and-mortar structure that results from templated growth of calcium carbonate on top of layers of ordered organic proteins. A key goal in this work, therefore, is to demonstrate a positive correlation between the order and orientation of the template layer and that of the crystalline ceramic material grown upon it. The work completed was comprised of several parallel efforts that encompassed the entire spectrum of biomimetic growth from solution. Studies were completed on seashells and the mechanisms of growth for calcium carbonate. Studies were completed on the characterization of LB films and the capability developed for the in-house fabrication of these films. Standard films of fatty acids were studied as well as novel polypeptides and porphyrins that were synthesized.

  1. Synthetic biology and biomimetic chemistry as converging technologies fostering a new generation of smart biosensors.

    Science.gov (United States)

    Scognamiglio, Viviana; Antonacci, Amina; Lambreva, Maya D; Litescu, Simona C; Rea, Giuseppina

    2015-12-15

    Biosensors are powerful tunable systems able to switch between an ON/OFF status in response to an external stimulus. This extraordinary property could be engineered by adopting synthetic biology or biomimetic chemistry to obtain tailor-made biosensors having the desired requirements of robustness, sensitivity and detection range. Recent advances in both disciplines, in fact, allow to re-design the configuration of the sensing elements - either by modifying toggle switches and gene networks, or by producing synthetic entities mimicking key properties of natural molecules. The present review considered the role of synthetic biology in sustaining biosensor technology, reporting examples from the literature and reflecting on the features that make it a useful tool for designing and constructing engineered biological systems for sensing application. Besides, a section dedicated to bioinspired synthetic molecules as powerful tools to enhance biosensor potential is reported, and treated as an extension of the concept of biomimetic chemistry, where organic synthesis is used to generate artificial molecules that mimic natural molecules. Thus, the design of synthetic molecules, such as aptamers, biomimetics, molecular imprinting polymers, peptide nucleic acids, and ribozymes were encompassed as "products" of biomimetic chemistry.

  2. A second-generation total synthesis of (+)-discodermolide: the development of a practical route using solely substrate-based stereocontrol.

    Science.gov (United States)

    Paterson, Ian; Delgado, Oscar; Florence, Gordon J; Lyothier, Isabelle; O'Brien, Matthew; Scott, Jeremy P; Sereinig, Natascha

    2005-01-01

    A novel total synthesis of the complex polyketide (+)-discodermolide, a promising anticancer agent of sponge origin, has been completed in 7.8% overall yield over 24 linear steps, with 35 steps altogether. This second-generation approach was designed to rely solely on substrate control for introduction of the required stereochemistry, eliminating the use of all chiral reagents or auxiliaries. The common 1,2-anti-2,3-syn stereotriad found in each of three subunits, aldehyde 9 (C(1)-C(5)), ester 40 (C(9)-C(16)), and aldehyde 13 (C(17)-C(24)), was established via a boron-mediated aldol reaction of ethyl ketone 15 and formaldehyde, followed by hydroxyl-directed reduction to give 1,3-diol 14. Alternatively, a surrogate aldehyde 22 was employed for formaldehyde in this aldol reaction, leading to the beta-hydroxy aldehyde 20 as a common building block, corresponding to the discodermolide stereotriad. Key fragment unions were achieved by a lithium-mediated anti aldol reaction of ester 40 and aldehyde 13 under Felkin-Anh control to provide (16S,17S)-adduct 51 and a boron-mediated aldol reaction between enone 10 and aldehyde 9, exploiting unprecedented remote 1,6-stereoinduction, to give the (5S)-adduct 57.

  3. Enantioselective total synthesis of epoxyquinone natural products (−)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (−)-panepophenanthrin: access to versatile chiral building blocks through enzymatic kinetic resolution

    OpenAIRE

    Mehta, Goverdhan; Islam, Kabirul

    2004-01-01

    A new enzyme mediated protocol to access versatile chiral building blocks for the synthesis of epoxyquinone natural products is delineated. Total syntheses of (−)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (−)-panepophenanthrin have been accomplished to demonstrate the efficacy of this approach.

  4. Total synthesis of cis-hydroazulene sesquiterpenes. Base-induced and -directed elimination and rearrangement reactions of perhydronaphthalene-1,4-diol monosulfonate esters.

    NARCIS (Netherlands)

    Jenniskens, L.H.D.

    1992-01-01

    The total synthesis of a number of cis-fused hydroazulene sesquiterpenes is described in this thesis. In this synthetic study, ample attention is paid to the mechanistic aspects of the base- induced and -directed rearrangement and elimination reactions of perhydronaphthalene-1,4-diol monosulfonate e

  5. 杀结核菌素的全合成研究%An Improved Total Synthesis of Tubercidin

    Institute of Scientific and Technical Information of China (English)

    黄海洋; 阮志忠; 胡韬; 肖强

    2014-01-01

    Tubercidin is a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside with significantly biological activities, such as anti-schistosomal, antibacterial and antitumor. An improved total synthesis of tubercidin is reported using microwave promoted Vorbrüggen glycosylation as the key step. Thus, tubercidin was synthesized in 3 steps with 74%overal yield using 6-chloro-7-bromo-pyrrolo[2,3-d]pyrimidine and 1-O-acetyl-2,3,5-O-tribenzoyl-β-D-ribose as starting materials. The applica-tion of micromave irridated one-pot reaction is also reported in the synthesis of 7-deazapurine nucleosides using potassium nonafluoro-1-butanesulfonate, trimethylsilyl chloride and silylation reagent [hexamethyldisilazane or N,O-bis(trimethyl-silyl)acetamide].%杀结核菌素是一个吡咯[2,3-d]嘧啶核苷天然产物,具有显著的抗血吸虫感染、抗菌和抗肿瘤活性。报道了以微波促进的Vorbrüggen糖基化反应为关键步骤,以6-氯-7-溴-吡咯[2,3-d]嘧啶和1-O-乙酰基-2,3,5-O-三苯甲酰基-β-D-呋喃核糖为原料,经过3步反应以74%的总收率完成了杀结核菌素的全合成。同时研究了以全氟丁基磺酸钾、三甲基氯硅烷和硅基化试剂[六甲基二硅胺烷或者N,O-双(三甲基硅基)乙酰胺]在微波加热下一锅法合成7-去氮嘌呤核苷的方法。

  6. Challenges in biomimetic design and innovation

    DEFF Research Database (Denmark)

    Lenau, Torben Anker; Barfoed, Michael; Shu, Li

    Biomimetic design copies desired principles found in nature and implement them into artificial applications. Applications could be products we use in our daily life but it can also be used to inspire material innovation. However there are significant challenges in performing biomimetic design. One....... This is a key issue in design and innovation work where problem identification and systematic search for suitable solution principle are major activities. One way to deal with this challenge is to use a biology search method. The use of such a method is illustrated with a case story describing the design...... including the terminology and knowledge organisation. It is often easy to recognise the splendour of a biological solution, but it can be much more difficult to understand the underlying mechanisms. Another challenge in biomimetic design is the search and identification of relevant solutions in nature...

  7. Laser technology in biomimetics basics and applications

    CERN Document Server

    Belegratis, Maria

    2013-01-01

    Lasers are progressively more used as versatile tools for fabrication purposes. The wide range of available powers, wavelengths, operation modes, repetition rates etc. facilitate the processing of a large spectrum of materials at exceptional precision and quality. Hence, manifold methods were established in the past and novel methods are continuously under development. Biomimetics, the translation from nature-inspired principles to technical applications, is strongly multidisciplinary. This field offers intrinsically a wide scope of applications for laser based methods regarding structuring and modification of materials. This book is dedicated to laser fabrication methods in biomimetics. It introduces both, a laser technology as well as an application focused approach.  The book covers the most important laser lithographic methods and various biomimetics application scenarios ranging from coatings and biotechnology to construction, medical applications and photonics.

  8. 以鱼鳞为模板合成仿生氧化铈及其性能%Synthesis and Performance of Biomimetic CeO2 Derived from Fish Scale

    Institute of Scientific and Technical Information of China (English)

    王炜; 陈志刚; 陈丰; 王太斌

    2012-01-01

    The biomimetic CeOz was obtained by using fish scales as biotemplate, and its structure and properties were characterized by Xray diffraction, field emission scanning electron microscopy, transmission electron microscopy and nitrogen adsorption-desorption measuring. The results show that the CeOz was the cubic fluorite structure with grain sizes of 5--7 nm, and a lot of pores with 2--5 nm were found in it. The prepared CeO2 displayed the superior photocatalytic activity for the degradation of acid fuchsin under sunqight irradiation, with a degradation rate as high as 90o/oo within 150 rain.%以鲫鱼鱼鳞为生物模板合成了仿生氧化铈;通过X射线衍射仪、场发射扫描电子显微镜、透射电子显微镜和N2吸附一脱附分析仪等对其结构与性能进行了表征。结果表明:所得氧化铈是由具有立方萤石结构的氧化铈组成,晶粒尺寸为5~7nm氧化铈中存在大量的微米及纳米孔,孔径集中分布于2~5nm;其在太阳光下表现出较强的光催化活性,150rain内其对酸性品红的降解率可达到909/5以上,远远高于市售氧化铈粉体的。

  9. Tissue bionics: examples in biomimetic tissue engineering

    International Nuclear Information System (INIS)

    Many important lessons can be learnt from the study of biological form and the functional design of organisms as design criteria for the development of tissue engineering products. This merging of biomimetics and regenerative medicine is termed 'tissue bionics'. Clinically useful analogues can be generated by appropriating, modifying and mimicking structures from a diversity of natural biomatrices ranging from marine plankton shells to sea urchin spines. Methods in biomimetic materials chemistry can also be used to fabricate tissue engineering scaffolds with added functional utility that promise human tissues fit for the clinic

  10. Minimally invasive restorative dentistry: a biomimetic approach.

    Science.gov (United States)

    Malterud, Mark I

    2006-08-01

    When providing dental treatment for a given patient, the practitioner should use a minimally invasive technique that conserves sound tooth structure as a clinical imperative. Biomimetics is a tenet that guides the author's practice and is generally described as the mimicking of natural life. This can be accomplished in many cases using contemporary composite resins and adhesive dental procedures. Both provide clinical benefits and support the biomimetic philosophy for treatment. This article illustrates a minimally invasive approach for the restoration of carious cervical defects created by poor hygiene exacerbated by the presence of orthodontic brackets.

  11. Tissue bionics: examples in biomimetic tissue engineering.

    Science.gov (United States)

    Green, David W

    2008-09-01

    Many important lessons can be learnt from the study of biological form and the functional design of organisms as design criteria for the development of tissue engineering products. This merging of biomimetics and regenerative medicine is termed 'tissue bionics'. Clinically useful analogues can be generated by appropriating, modifying and mimicking structures from a diversity of natural biomatrices ranging from marine plankton shells to sea urchin spines. Methods in biomimetic materials chemistry can also be used to fabricate tissue engineering scaffolds with added functional utility that promise human tissues fit for the clinic.

  12. Biomimetic catalysts responsive to specific chemical signals

    Energy Technology Data Exchange (ETDEWEB)

    Zhao, Yan [Iowa State Univ., Ames, IA (United States)

    2015-03-04

    Part 1. Design of Biomimetic Catalysts Based on Amphiphilic Systems The overall objective of our research is to create biomimetic catalysts from amphiphilic molecules. More specifically, we aim to create supramolecular systems that can be used to control the microenvironment around a catalytic center in a biomimetic fashion and apply the learning to construct supramolecular catalysts with novel functions found in enzymatic catalysts. We have prepared synthetic molecules (i.e., foldamers) that could fold into helical structures with nanometer-sized internal hydrophilic cavities. Cavities of this size are typically observed only in the tertiary and quaternary structures of proteins but were formed in our foldamer prepared in just a few steps from the monomer. Similar to many proteins, our foldamers displayed cooperativity in the folding/unfolding equilibrium and followed a two-state conformational transition. In addition, their conformational change could be triggered by solvent polarity, pH, or presence of metal ions and certain organic molecules. We studied their environmentally dependent conformational changes in solutions, surfactant micelles, and lipid bilayer membranes. Unlike conventional rigid supramolecular host, a foldamer undergoes conformational change during guest binding. Our study in the molecular recognition of an oligocholate host yielded some extremely exciting results. Cooperativity between host conformation and host–guest interactions was found to “magnify” weak binding interactions. In other words, since binding affinity is determined by the overall change of free energy during the binding, guest-induced conformational change of the host, whether near or far from the binding site, affects the binding. This study has strong implications in catalysis because enzymes have been hypothesized to harvest similar intramolecular forces to strengthen their binding with the transition state of an enzyme-catalyzed reaction. The supramolecular and

  13. Pharmacophore mapping in the laulimalide series: total synthesis of a vinylogue for a late-stage metathesis diversification strategy.

    Science.gov (United States)

    Wender, Paul A; Hilinski, Michael K; Skaanderup, Philip R; Soldermann, Nicolas G; Mooberry, Susan L

    2006-08-31

    An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.

  14. Proteins and Peptides in Biomimetic Polymeric Membranes

    DEFF Research Database (Denmark)

    Perez, Alfredo Gonzalez

    2013-01-01

    This chapter discusses recent advances and the main advantages of block copolymers for functional membrane protein reconstitution in biomimetic polymeric membranes. A rational approach to the reconstitution of membrane proteins in a functional form can be addressed by a more holistic view by usin...

  15. Major intrinsic proteins in biomimetic membranes.

    Science.gov (United States)

    Nielsen, Claus Hélix

    2010-01-01

    Biological membranes define the structural and functional boundaries in living cells and their organelles. The integrity of the cell depends on its ability to separate inside from outside and yet at the same time allow massive transport of matter in and out the cell. Nature has elegantly met this challenge by developing membranes in the form of lipid bilayers in which specialized transport proteins are incorporated. This raises the question: is it possible to mimic biological membranes and create a membrane based sensor and/or separation device? In the development of a biomimetic sensor/separation technology, a unique class of membrane transport proteins is especially interesting-the major intrinsic proteins (MIPs). Generally, MIPs conduct water molecules and selected solutes in and out of the cell while preventing the passage of other solutes, a property critical for the conservation of the cells internal pH and salt concentration. Also known as water channels or aquaporins they are highly efficient membrane pore proteins some of which are capable of transporting water at very high rates up to 10(9) molecules per second. Some MIPs transport other small, uncharged solutes, such as glycerol and other permeants such as carbon dioxide, nitric oxide, ammonia, hydrogen peroxide and the metalloids antimonite, arsenite, silicic and boric acid depending on the effective restriction mechanism of the protein. The flux properties of MIPs thus lead to the question ifMIPs can be used in separation devices or as sensor devices based on, e.g., the selective permeation of metalloids. In principle a MIP based membrane sensor/separation device requires the supporting biomimetic matrix to be virtually impermeable to anything but water or the solute in question. In practice, however, a biomimetic support matrix will generally have finite permeabilities to both electrolytes and non-electrolytes. The feasibility of a biomimetic MIP device thus depends on the relative transport

  16. Improved Total Synthesis and Biological Evaluation of Potent Apratoxin S4 Based Anticancer Agents with Differential Stability and Further Enhanced Activity

    OpenAIRE

    Chen, Qi-Yin; Liu, Yanxia; Cai, Weijing; Luesch, Hendrik

    2014-01-01

    Apratoxins are cytotoxic natural products originally isolated from marine cyanobacteria that act by preventing cotranslational translocation early in the secretory pathway to downregulate receptor levels and inhibit growth factor secretion, leading to potent antiproliferative activity. Through rational design and total synthesis of an apratoxin A/E hybrid, apratoxin S4 (1a), we have previously improved the antitumor activity and tolerability in vivo. Compound 1a and newly designed analogues a...

  17. Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine

    DEFF Research Database (Denmark)

    Nielsen, Thomas Eiland; Tanner, David Ackland

    2002-01-01

    (E)-beta-Trialkylstannyl-alpha,beta-unsaturated ketones are readily available from secondary propargylic alcohols via a two-step sequence involving highly regio- and stereoselective Pd(0)-catalyzed hydrostannation followed by mild oxidation (TPAP). The methodology has been applied to the synthesi...

  18. A water-forming NADH oxidase from Lactobacillus pentosus and its potential application in the regeneration of synthetic biomimetic cofactors

    Directory of Open Access Journals (Sweden)

    Claudia eNowak

    2015-09-01

    Full Text Available The cell-free biocatalytic production of fine chemicals by oxidoreductases has continuously grown over the past years. Since especially dehydrogenases depend on the stoichiometric use of nicotinamide pyridine cofactors, an integrated efficient recycling system is crucial to allow process operation under economic conditions. Lately, the variety of cofactors for biocatalysis was broadened by the utilization of totally synthetic and cheap biomimetics. Though, to date the regeneration has been limited to chemical or electrochemical methods. Here, we report an enzymatic recycling by the flavoprotein NADH-oxidase from Lactobacillus pentosus (LpNox. Since this enzyme has not been described before, we first characterized it in regard to its optimal reaction parameters. We found that the heterologously overexpressed enzyme only contained 13 % FAD. In vitro loading of the enzyme with FAD, resulted in a higher specific activity towards its natural cofactor NADH as well as different nicotinamide derived biomimetics. Apart from the enzymatic recycling, which gives water as a by-product by transferring four electrons onto oxygen, unbound FAD can also catalyse the oxidation of biomimetic cofactors. Here a two electron process takes place yielding H2O2 instead. The enzymatic and chemical recycling was compared in regard to reaction kinetics for the natural and biomimetic cofactors. With LpNox and FAD, two recycling strategies for biomimetic cofactors are described with either water or hydrogen peroxide as a by-product.

  19. Piezoelectric Templates - New Views on Biomineralization and Biomimetics.

    Science.gov (United States)

    Stitz, Nina; Eiben, Sabine; Atanasova, Petia; Domingo, Neus; Leineweber, Andreas; Burghard, Zaklina; Bill, Joachim

    2016-05-23

    Biomineralization in general is based on electrostatic interactions and molecular recognition of organic and inorganic phases. These principles of biomineralization have also been utilized and transferred to bio-inspired synthesis of functional materials during the past decades. Proteins involved in both, biomineralization and bio-inspired processes, are often piezoelectric due to their dipolar character hinting to the impact of a template's piezoelectricity on mineralization processes. However, the piezoelectric contribution on the mineralization process and especially the interaction of organic and inorganic phases is hardly considered so far. We herein report the successful use of the intrinsic piezoelectric properties of tobacco mosaic virus (TMV) to synthesize piezoelectric ZnO. Such films show a two-fold increase of the piezoelectric coefficient up to 7.2 pm V(-1) compared to films synthesized on non-piezoelectric templates. By utilizing the intrinsic piezoelectricity of a biotemplate, we thus established a novel synthesis pathway towards functional materials, which sheds light on the whole field of biomimetics. The obtained results are of even broader and general interest since they are providing a new, more comprehensive insight into the mechanisms involved into biomineralization in living nature.

  20. Jacobsen Catalyst as a Cytochrome P450 Biomimetic Model for the Metabolism of Monensin A

    Directory of Open Access Journals (Sweden)

    Bruno Alves Rocha

    2014-01-01

    Full Text Available Monensin A is a commercially important natural product isolated from Streptomyces cinnamonensins that is primarily employed to treat coccidiosis. Monensin A selectively complexes and transports sodium cations across lipid membranes and displays a variety of biological properties. In this study, we evaluated the Jacobsen catalyst as a cytochrome P450 biomimetic model to investigate the oxidation of monensin A. Mass spectrometry analysis of the products from these model systems revealed the formation of two products: 3-O-demethyl monensin A and 12-hydroxy monensin A, which are the same ones found in in vivo models. Monensin A and products obtained in biomimetic model were tested in a mitochondrial toxicity model assessment and an antimicrobial bioassay against Staphylococcus aureus, S. aureus methicillin-resistant, Staphylococcus epidermidis, Pseudomonas aeruginosa, and Escherichia coli. Our results demonstrated the toxicological effects of monensin A in isolated rat liver mitochondria but not its products, showing that the metabolism of monensin A is a detoxification metabolism. In addition, the antimicrobial bioassay showed that monensin A and its products possessed activity against Gram-positive microorganisms but not for Gram-negative microorganisms. The results revealed the potential of application of this biomimetic chemical model in the synthesis of drug metabolites, providing metabolites for biological tests and other purposes.

  1. Advances in total synthesis: A new approach to the synthesis of pteridic acids A and B [Avanços em síntese total: Uma nova abordagem para a síntese dos ácidos pterídicos A e B

    Directory of Open Access Journals (Sweden)

    David Rodrigues da Rocha

    2009-08-01

    Full Text Available This communication overview the total synthesis of pteridic acids A and B recently published by L. C. Dias and A. G. Salles Jr.in The Journal of Organic Chemistry which was achieved by a new synthetic route. These natural products are among the mostcomplex molecules already synthesized in Brazil.

  2. Efficient Enzyme-Free Biomimetic Sensors for Natural Phenol Detection.

    Science.gov (United States)

    Ferreira Garcia, Luane; Ribeiro Souza, Aparecido; Sanz Lobón, Germán; Dos Santos, Wallans Torres Pio; Alecrim, Morgana Fernandes; Fontes Santiago, Mariângela; de Sotomayor, Rafael Luque Álvarez; de Souza Gil, Eric

    2016-01-01

    The development of sensors and biosensors based on copper enzymes and/or copper oxides for phenol sensing is disclosed in this work. The electrochemical properties were studied by cyclic and differential pulse voltammetry using standard solutions of potassium ferrocyanide, phosphate/acetate buffers and representative natural phenols in a wide pH range (3.0 to 9.0). Among the natural phenols herein investigated, the highest sensitivity was observed for rutin, a powerful antioxidant widespread in functional foods and ubiquitous in the plant kingdom. The calibration curve for rutin performed at optimum pH (7.0) was linear in a broad concentration range, 1 to 120 µM (r = 0.99), showing detection limits of 0.4 µM. The optimized biomimetic sensor was also applied in total phenol determination in natural samples, exhibiting higher stability and sensitivity as well as distinct selectivity for antioxidant compounds. PMID:27529208

  3. The Effect of Prolonged Fasting on Total Lipid Synthesis and Enzyme Activities in the Liver of the European Eel (Anguilla anguilla)

    DEFF Research Database (Denmark)

    Abraham, S. A.; Hansen, Heinz Johs. Max; Hansen, F.N.

    1984-01-01

    The extent of fatty acid synthesis from [1-14C]acetate in liver slices was reduced 6-fold when eels were fasted for 1-7 wk and 20-fold when fasted for 39 wk, thereafter hepatic lipogenesis seemed to remain constant for up to 95 wk of fasting. After a 1-3 wk fast some hepatic enzyme activities were...... total lipid synthesis and lipogenic enzyme activity in eel liver was 30.degree. C....... reduced (acetyl-CoA carboxylase decreased 2-fold and fatty acid synthetase declined 5-fold); others remained unchanged (G-6-P dehydrogenase, 6-phosphogluconate dehydrogenase, .alpha.-glycerol phosphate dehydrogenase as well as malic enzyme and ATP-citrate lyase). The optimum temperature for measuring both...

  4. Bringing the science of proteins into the realm of organic chemistry: total chemical synthesis of SEP (synthetic erythropoiesis protein).

    Science.gov (United States)

    Kent, Stephen B H

    2013-11-11

    Erythropoietin, commonly known as EPO, is a glycoprotein hormone that stimulates the production of red blood cells. Recombinant EPO has been described as "arguably the most successful drug spawned by the revolution in recombinant DNA technology". Recently, the EPO glycoprotein molecule has re-emerged as a major target of synthetic organic chemistry. In this article I will give an account of an important body of earlier work on the chemical synthesis of a designed EPO analogue that had full biological activity and improved pharmacokinetic properties. The design and synthesis of this "synthetic erythropoiesis protein" was ahead of its time, but has gained new relevance in recent months. Here I will document the story of one of the major accomplishments of synthetic chemistry in a more complete way than is possible in the primary literature, and put the work in its contemporaneous context.

  5. The Top of the Biomimetic Triangle

    Institute of Scientific and Technical Information of China (English)

    Andrei P. Sommer; Dan Zhu; Matthias Wiora; Hans-Joerg Fecht

    2008-01-01

    There is increasing observational evidence indicating that crystalline interfacial water layers play a central role in evolution and biology. For instance in cellular recognition processes, in particular during first contact events, where cells decide upon survival or entering apoptosis. Understanding water layers is thus crucial in biomedical engineering, specifically in the design of biomaterials inspired by biomimetic principles. Whereas there is ample experimental evidence for crystalline interfacial water layers on surfaces in air, their subaquatic presence could not be verified directly, so far. Analysing a polarity dependent asym- metry in the surface conductivity on hydrogenated nanocrystalline diamond, we show that crystalline interfacial water layers persist subaquatically. Nanoscopic interfacial water layers with an order different from that of bulk water have been identified at room temperature on both hydrophilic and hydrophobic model surfaces - in air and subaquatically. Their generalization and systematic inclusion into the catalogue of physical and chemical determinants of biocompatibility complete the biomimetic triangle.

  6. Green Tribology Biomimetics, Energy Conservation and Sustainability

    CERN Document Server

    Bhushan, Bharat

    2012-01-01

    Tribology is the study of friction, wear and lubrication. Recently, the concept of “green tribology” as “the science and technology of the tribological aspects of ecological balance and of environmental and biological impacts” was introduced. The field of green tribology includes tribological technology that mimics living nature (biomimetic surfaces) and thus is expected to be environmentally friendly, the control of friction and wear that is of importance for energy conservation and conversion, environmental aspects of lubrication and surface modification techniques, and tribological aspects of green applications such as wind-power turbines or solar panels. This book is the first comprehensive volume on green tribology. The chapters are prepared by leading experts in their fields and cover such topics as biomimetics, environmentally friendly lubrication, tribology of wind turbines and renewable sources of energy, and ecological impact of new technologies of surface treatment.

  7. Action of Chicory Fructooligosaccharides on Biomimetic Membranes

    OpenAIRE

    Barbosa, A. F.; Henrique, R. S.; A. S. Lucho; V. Paffaro; J.M. Schneedorf

    2014-01-01

    Fructooligosaccharides from chicory (FOSC) are functional prebiotic foods recognized to exert several well-being effects in human health and animal production, as decreasing blood lipids, modulating the gut immune system, enhancing mineral bioavailability, and inhibiting microbial growth, among others. Mechanisms of actions directly on cell metabolism and structure are however little known. In this sense this work was targeted to investigate the interaction of FOSC with biomimetic membranes (...

  8. Design of graded biomimetic osteochondral composite scaffolds

    OpenAIRE

    Tampieri, Anna; Sandri, Monica; Landi, Elena; Pressato, Daniele; Francioli, Silvia; Quarto, Rodolfo; Martin, Ivan

    2008-01-01

    With the ultimate goal to generate suitable materials for the repair of osteochondral defects, in this work we aimed at developing composite osteochondral scaffolds organized in different integrated layers, with features which are biomimetic for articular cartilage and subchondral bone and can differentially support formation of such tissues. A biologically inspired mineralization process was first developed to nucleate Mg-doped hydroxyapatite crystals on type I collagen fibers during their s...

  9. Embedded SMA wire actuated biomimetic fin: a module for biomimetic underwater propulsion

    Science.gov (United States)

    Wang, Zhenlong; Hang, Guanrong; Wang, Yangwei; Li, Jian; Du, Wei

    2008-04-01

    An embedded shape memory alloy (SMA) wire actuated biomimetic fin is presented, and based on this module for biomimetic underwater propulsion, a micro robot fish (146 mm in length, 30 g in weight) and a robot squid (242 mm in length, 360 g in weight) were developed. Fish swim by undulating their body and/or fins. Squid and cuttlefish can also swim by undulating their fins. To simplify engineering modeling, the undulating swimming movement is assumed to be the integration of the movements of many flexible bending segments connected in parallel or in series. According to this idea, a biomimetic fin which can bend flexibly was developed. The musculature of a cuttlefish fin was investigated to aid the design of the biomimetic fin. SMA wires act as 'muscle fibers' to drive the biomimetic fin just like the transverse muscles of the cuttlefish fin. During the bending phase, elastic energy is stored in the elastic substrate and skin, and during the return phase, elastic energy is released to power the return movement. Theorem analysis of the bending angle was performed to estimate the bending performance of the biomimetic fin. Experiments were carried out on single-face fins with latex rubber skin and silicone skin (SF-L and SF-S) to compare the bending angle, return time, elastic energy storage and reliability. Silicone was found to be the better skin. A dual-face fin with silicone skin (DF-S) was tested in water to evaluate the actuating performance and to validate the reliability. Thermal analysis of the SMA temperature was performed to aid the control strategy. The micro robot fish and robot squid employ one and ten DF-S, respectively. Swimming experiments with different actuation frequencies were carried out. The speed and steering radius of the micro robot fish reached 112 mm s-1 and 136 mm, respectively, and the speed and rotary speed of the robot squid reached 40 mm s-1 and 22° s-1, respectively.

  10. Embedded SMA wire actuated biomimetic fin: a module for biomimetic underwater propulsion

    International Nuclear Information System (INIS)

    An embedded shape memory alloy (SMA) wire actuated biomimetic fin is presented, and based on this module for biomimetic underwater propulsion, a micro robot fish (146 mm in length, 30 g in weight) and a robot squid (242 mm in length, 360 g in weight) were developed. Fish swim by undulating their body and/or fins. Squid and cuttlefish can also swim by undulating their fins. To simplify engineering modeling, the undulating swimming movement is assumed to be the integration of the movements of many flexible bending segments connected in parallel or in series. According to this idea, a biomimetic fin which can bend flexibly was developed. The musculature of a cuttlefish fin was investigated to aid the design of the biomimetic fin. SMA wires act as 'muscle fibers' to drive the biomimetic fin just like the transverse muscles of the cuttlefish fin. During the bending phase, elastic energy is stored in the elastic substrate and skin, and during the return phase, elastic energy is released to power the return movement. Theorem analysis of the bending angle was performed to estimate the bending performance of the biomimetic fin. Experiments were carried out on single-face fins with latex rubber skin and silicone skin (SF-L and SF-S) to compare the bending angle, return time, elastic energy storage and reliability. Silicone was found to be the better skin. A dual-face fin with silicone skin (DF-S) was tested in water to evaluate the actuating performance and to validate the reliability. Thermal analysis of the SMA temperature was performed to aid the control strategy. The micro robot fish and robot squid employ one and ten DF-S, respectively. Swimming experiments with different actuation frequencies were carried out. The speed and steering radius of the micro robot fish reached 112 mm s−1 and 136 mm, respectively, and the speed and rotary speed of the robot squid reached 40 mm s−1 and 22° s−1, respectively

  11. Biomimetic Composite Structural T-joints

    Institute of Scientific and Technical Information of China (English)

    Vimal Kumar Thummalapalli; Steven L.Donaldson

    2012-01-01

    Biological structural fixed joints exhibit unique attributes,including highly optimized fiber paths which minimize stress concentrations.In addition,since the joints consist of continuous,uncut fiber architectures,the joints enable the organism to transport information and chemicals from one part of the body to the other.To the contrary,sections of man-made composite material structures are often joined using bolted or bonded joints,which involve low strength and high stress concentrations.These methods are also expensive to achieve.Additional functions such as fluid transport,electrical signal delivery,and thermal conductivity across the joints typically require parasitic tubes,wires,and attachment clips.By using the biomimetic methods,we seek to overcome the limitations which are present in the conventional methods. In the present work,biomimetic co-cured composite sandwich T-joints were constructed using unidirectional glass fiber,epoxy resin,and structural foam.The joints were fabricated using the wet lay-up vacuum bag resin infusion method.Foam sandwich T-joints with multiple continuous fiber architectures and sandwich foam thickness were prepared.The designs were tested in quasi-static bending using a mechanical load frame.The significantweight savings using the biomimetic approaches is discussed,as well as a comparison of failure modes versus architecture is described.

  12. Biomimetic nanoparticles: preparation, characterization and biomedical applications

    Directory of Open Access Journals (Sweden)

    Ana Maria Carmona-Ribeiro

    2010-04-01

    Full Text Available Ana Maria Carmona-RibeiroBiocolloids Lab, Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, São Paulo, BrazilAbstract: Mimicking nature is a powerful approach for developing novel lipid-based devices for drug and vaccine delivery. In this review, biomimetic assemblies based on natural or synthetic lipids by themselves or associated to silica, latex or drug particles will be discussed. In water, self-assembly of lipid molecules into supramolecular structures is fairly well understood. However, their self-assembly on a solid surface or at an interface remains poorly understood. In certain cases, hydrophobic drug granules can be dispersed in aqueous solution via lipid adsorption surrounding the drug particles as nanocapsules. In other instances, hydrophobic drug molecules attach as monomers to borders of lipid bilayer fragments providing drug formulations that are effective in vivo at low drug-to-lipid-molar ratio. Cationic biomimetic particles offer suitable interfacial environment for adsorption, presentation and targeting of biomolecules in vivo. Thereby antigens can effectively be presented by tailored biomimetic particles for development of vaccines over a range of defined and controllable particle sizes. Biomolecular recognition between receptor and ligand can be reconstituted by means of receptor immobilization into supported lipidic bilayers allowing isolation and characterization of signal transduction steps.Keywords: cationic lipid, phospholipids, bilayer fragments, vesicles, silica, polymeric particles, antigens, novel cationic immunoadjuvants, drugs

  13. Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity.

    Science.gov (United States)

    Steele, Andrew D; Keohane, Colleen E; Knouse, Kyle W; Rossiter, Sean E; Williams, Sierra J; Wuest, William M

    2016-05-11

    Promysalin is a species-specific Pseudomonad metabolite with unique bioactivity. To better understand the mode of action of this natural product, we synthesized 16 analogs utilizing diverted total synthesis (DTS). Our analog studies revealed that the bioactivity of promysalin is sensitive to changes within its hydrogen bond network whereby alteration has drastic biological consequences. The DTS library not only yielded three analogs that retained potency but also provided insights that resulted in the identification of a previously unknown ability of promysalin to bind iron. These findings coupled with previous observations hint at a complex multifaceted role of the natural product within the rhizosphere.

  14. Total synthesis of (+)-discodermolide: an improved endgame exploiting a Still-Gennari-type olefination with a C1-C8 beta-ketophosphonate fragment.

    Science.gov (United States)

    Paterson, Ian; Lyothier, Isabelle

    2004-12-23

    [structure: see text] An improved, third-generation, total synthesis of (+)-discodermolide, a potent microtubule-stabilizing anticancer agent of marine sponge origin, is achieved in 11.1% yield over 21 steps. Key steps include a Still-Gennari HWE olefination, performed using NaH as the base, between C1-C8 beta-ketophosphonate 7 and C9-C24 aldehyde 8, introducing the (8Z)-alkene with 10:1 selectivity, and K-Selectride reduction of the derived enone 16, installing the (7S)-configuration.

  15. Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation.

    Science.gov (United States)

    Mahajan, Pankaj S; Humne, Vivek T; Tanpure, Subhash D; Mhaske, Santosh B

    2016-07-15

    The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and (18)O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C-H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine. PMID:27377995

  16. Improved total synthesis and biological evaluation of potent apratoxin S4 based anticancer agents with differential stability and further enhanced activity.

    Science.gov (United States)

    Chen, Qi-Yin; Liu, Yanxia; Cai, Weijing; Luesch, Hendrik

    2014-04-10

    Apratoxins are cytotoxic natural products originally isolated from marine cyanobacteria that act by preventing cotranslational translocation early in the secretory pathway to downregulate receptor levels and inhibit growth factor secretion, leading to potent antiproliferative activity. Through rational design and total synthesis of an apratoxin A/E hybrid, apratoxin S4 (1a), we have previously improved the antitumor activity and tolerability in vivo. Compound 1a and newly designed analogues apratoxins S7-S9 (1b-d), with various degrees of methylation at C34 (1b,c) or epimeric configuration at C30 (1d), were efficiently synthesized utilizing improved procedures. Optimizations have been applied to the synthesis of key intermediate aldehyde 7 and further include the application of Leighton's silanes and modifications of Kelly's methods to induce thiazoline ring formation in other crucial steps of the apratoxin synthesis. Apratoxin S9 (1d) exhibited increased activity with subnanomolar potency. Apratoxin S8 (1c) lacks the propensity to be deactivated by dehydration and showed efficacy in a human HCT116 xenograft mouse model.

  17. Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide: Application to an Analogue of Human Insulin-Like Peptide 3

    Science.gov (United States)

    Karas, John; Shabanpoor, Fazel; Hossain, Mohammed Akhter; Wade, John D.; Scanlon, Denis B.

    2013-01-01

    Nonreducible cystine isosteres represent important peptide design elements in that they can maintain a near-native tertiary conformation of the peptide while simultaneously extending the in vitro and in vivo half-life of the biomolecule. Examples of these cystine mimics include dicarba, diselenide, thioether, triazole, and lactam bridges. Each has unique physicochemical properties that impact upon the resulting peptide conformation. Each also requires specific conditions for its formation via chemical peptide synthesis protocols. While the preparation of peptides containing two lactam bonds within a peptide is technically possible and reported by others, to date there has been no report of the chemical synthesis of a heterodimeric peptide linked by two lactam bonds. To examine the feasibility of such an assembly, judicious use of a complementary combination of amine and acid protecting groups together with nonfragment-based, total stepwise solid phase peptide synthesis led to the successful preparation of an analogue of the model peptide, insulin-like peptide 3 (INSL3), in which both of the interchain disulfide bonds were replaced with a lactam bond. An analogue containing a single disulfide-substituted interchain lactam bond was also prepared. Both INSL3 analogues retained significant cognate RXFP2 receptor binding affinity. PMID:24288548

  18. Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide: Application to an Analogue of Human Insulin-Like Peptide 3

    Directory of Open Access Journals (Sweden)

    John Karas

    2013-01-01

    Full Text Available Nonreducible cystine isosteres represent important peptide design elements in that they can maintain a near-native tertiary conformation of the peptide while simultaneously extending the in vitro and in vivo half-life of the biomolecule. Examples of these cystine mimics include dicarba, diselenide, thioether, triazole, and lactam bridges. Each has unique physicochemical properties that impact upon the resulting peptide conformation. Each also requires specific conditions for its formation via chemical peptide synthesis protocols. While the preparation of peptides containing two lactam bonds within a peptide is technically possible and reported by others, to date there has been no report of the chemical synthesis of a heterodimeric peptide linked by two lactam bonds. To examine the feasibility of such an assembly, judicious use of a complementary combination of amine and acid protecting groups together with nonfragment-based, total stepwise solid phase peptide synthesis led to the successful preparation of an analogue of the model peptide, insulin-like peptide 3 (INSL3, in which both of the interchain disulfide bonds were replaced with a lactam bond. An analogue containing a single disulfide-substituted interchain lactam bond was also prepared. Both INSL3 analogues retained significant cognate RXFP2 receptor binding affinity.

  19. Towards the LIVING envelope: Biomimetics for building envelope adaptation

    NARCIS (Netherlands)

    Badarnah Kadri, L.

    2012-01-01

    Several biomimetic design strategies are available for various applications, though the research on biomimetics as a design tool in architecture is still challenging. This is due to a lack of systematic design tools required for identifying relevant organisms, or natural systems, and abstracting the

  20. 仿生合成羟基锡酸锌包覆碳酸钙及其对PVC的阻燃研究%Biomimetic synthesis of zinc hydroxystannate-coated calcium carbonate and its application in PVC*

    Institute of Scientific and Technical Information of China (English)

    焦运红; 彭飞; 徐建中; 谢吉星; 王宁

    2011-01-01

    Taking sodium dodecyl benzene suffonate(SDBS)as the template in the water solution, zinc hydroxystannate-coated calcium carbonate (ZHSCC-1)was prepared by biominetic synthesis method, and zinc hydroxystannate-coated calcium carbonate (ZHSCC-2)was also prepared in water solution without SDBS. Both ZHSCC-1 and ZHSCC-2 were studied as the flame retardant of PVC. The results showed that, when ZHSCC at the same addition level, not only the flame retardant and smoke suppressant effects of ZHSCC-1 were better than those of ZHSCC-2, but also the beneficial effects of the former were better than those of the latter.%采用仿生合成的方法,以十二烷基苯磺酸钠(SDBS)为模板,在水溶液中制备了羟基锡酸锌包覆碳酸钙(ZHSCC-1),并将其和不添加SDBS模板制备的羟基锡酸锌包覆碳酸钙(ZHSCC-2)分别应用在PVC 中进行对比研究.结果表明:在ZHSCC含量相同时,ZHSCC-1对PVC的阻燃消烟效果明显优于ZHSCC-2,且前者对PVC的拉伸强度、断裂伸长率、抗冲强度的有益影响都优于后者.

  1. Biomimetics: forecasting the future of science, engineering, and medicine.

    Science.gov (United States)

    Hwang, Jangsun; Jeong, Yoon; Park, Jeong Min; Lee, Kwan Hong; Hong, Jong Wook; Choi, Jonghoon

    2015-01-01

    Biomimetics is the study of nature and natural phenomena to understand the principles of underlying mechanisms, to obtain ideas from nature, and to apply concepts that may benefit science, engineering, and medicine. Examples of biomimetic studies include fluid-drag reduction swimsuits inspired by the structure of shark's skin, velcro fasteners modeled on burrs, shape of airplanes developed from the look of birds, and stable building structures copied from the backbone of turban shells. In this article, we focus on the current research topics in biomimetics and discuss the potential of biomimetics in science, engineering, and medicine. Our report proposes to become a blueprint for accomplishments that can stem from biomimetics in the next 5 years as well as providing insight into their unseen limitations.

  2. Porous metal-organic frameworks for heterogeneous biomimetic catalysis.

    Science.gov (United States)

    Zhao, Min; Ou, Sha; Wu, Chuan-De

    2014-04-15

    Metalloporphyrins are the active sites in monooxygenases that oxidize a variety of substrates efficiently and under mild conditions. Researchers have developed artificial metalloporphyrins, but these structures have had limited catalytic applications. Homogeneous artificial metalloporphyrins can undergo catalytic deactivation via suicidal self-oxidation, which lowers their catalytic activity and sustainability relative to their counterparts in Nature. Heme molecules in protein scaffolds can maintain high efficiency over numerous catalytic cycles. Therefore, we wondered if immobilizing metalloporphyrin moieties within porous metal-organic frameworks (MOFs) could stabilize these structures and facilitate the molecular recognition of substrates and produce highly efficient biomimetic catalysis. In this Account, we describe our research to develop multifunctional porphyrinic frameworks as highly efficient heterogeneous biomimetic catalysts. Our studies indicate that porous porphyrinic frameworks provide an excellent platform for mimicking the activity of biocatalysts and developing new heterogeneous catalysts that effect new chemical transformations under mild conditions. The porous structures and framework topologies of the porphyrinic frameworks depend on the configurations, coordination donors, and porphyrin metal ions of the metalloporphyrin moieties. To improve the activity of porous porphyrinic frameworks, we have developed a two-step synthesis that introduces the functional polyoxometalates (POMs) into POM-porphyrin hybrid materials. To tune the pore structures and the catalytic properties of porphyrinic frameworks, we have designed metalloporphyrin M-H8OCPP ligands with four m-benzenedicarboxylate moieties, and introduced the secondary auxiliary ligands. The porphyrin metal ions and the secondary functional moieties that are incorporated into porous metal-organic frameworks greatly influence the catalytic properties and activities of porphyrinic frameworks in

  3. Tailored antireflective biomimetic nanostructures for UV applications

    Energy Technology Data Exchange (ETDEWEB)

    Morhard, Christoph; Pacholski, Claudia; Spatz, Joachim P [Department of New Materials and Biosystems, Max Planck Institute for Metals Research, Heisenbergstrasse 3, D-70569 Stuttgart (Germany); Lehr, Dennis; Brunner, Robert; Helgert, Michael [Carl Zeiss Jena GmbH, Technology Center, Carl-Zeiss-Promenade 10, D-07745 Jena (Germany); Sundermann, Michael, E-mail: Pacholski@mf.mpg.de [Carl Zeiss Jena GmbH, Technology Center, Carl-Zeiss-Strasse 56, D-73447 Oberkochen (Germany)

    2010-10-22

    Antireflective surfaces composed of biomimetic sub-wavelength structures that employ the 'moth eye principle' for reflectance reduction are highly desirable in many optical applications such as solar cells, photodetectors and laser optics. We report an efficient approach for the fabrication of antireflective surfaces based on a two-step process consisting of gold nanoparticle mask generation by micellar block copolymer nanolithography and a multi-step reactive ion etching process. Depending on the RIE process parameters nanostructured surfaces with tailored antireflective properties can easily be fabricated that show optimum performance for specific applications.

  4. Biomimetic magnetic nanocomposite for smart skins

    KAUST Repository

    Alfadhel, Ahmed

    2015-11-01

    We report a biomimetic tactile sensor consisting of magnetic nanocomposite artificial cilia and magnetic sensors. The nanocomposite is fashioned from polydimethylsiloxane and iron nanowires and exhibits a permanent magnetic behavior. This enables remote operation without an additional magnetic field to magnetize the nanowires, which simplifies device integration. Moreover, the highly elastic and easy patternable nanocomposite is corrosion resistant and thermally stable. The highly sensitive and power efficient tactile sensors can detect vertical and shear forces from interactions with objects. The sensors can operate in dry and wet environment with the ability to measure different properties such as the texture and the movement or stability of objects, with easily adjustable performance.

  5. Effect of urea on biomimetic aggregates

    Directory of Open Access Journals (Sweden)

    F.H. Florenzano

    1997-02-01

    Full Text Available The effect of urea on biomimetic aggregates (aqueous and reversed micelles, vesicles and monolayers was investigated to obtain insights into the effect of the denaturant on structured macromolecules. Direct evidence obtained from light scattering (static and dynamic, monolayer maximum isothermal compression and ionic conductivity measurements, together with indirect evidence from fluorescence photodissociation, fluorescence suppression, and thermal reactions, strongly indicates the direct interaction mechanism of urea with the aggregates. Preferential solvation of the surfactant headgroups by urea results in an increase in the monomer dissociation degree (when applied, which leads to an increase in the area per headgroup and also in the loss of counterion affinities

  6. Effect of urea on biomimetic aggregates.

    Science.gov (United States)

    Florenzano, F H; Politi, M J

    1997-02-01

    The effect of urea on biomimetic aggregates (aqueous and reversed micelles, vesicles and monolayers) was investigated to obtain insights into the effect of the denaturant on structured macromolecules. Direct evidence obtained from light scattering (static and dynamic), monolayer maximum isothermal compression and ionic conductivity measurements, together with indirect evidence from fluorescence photodissociation, fluorescence suppression, and thermal reactions, strongly indicates the direct interaction mechanism of urea with the aggregates. Preferential solvation of the surfactant headgroups by urea results in an increase in the monomer dissociation degree (when applied), which leads to an increase in the area per headgroup and also in the loss of counterion affinities. PMID:9239302

  7. Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues

    Directory of Open Access Journals (Sweden)

    Tao Jiang

    2013-04-01

    Full Text Available Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1–Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y1–Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15–63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y1–Y7.

  8. Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

    Science.gov (United States)

    Araoz, Romulo; Servent, Denis; Molgó, Jordi; Iorga, Bogdan I; Fruchart-Gaillard, Carole; Benoit, Evelyne; Gu, Zhenhua; Stivala, Craig; Zakarian, Armen

    2011-07-13

    Pinnatoxins belong to an emerging class of potent marine toxins of the cyclic imine group. Detailed studies of their biological effects have been impeded by unavailability of the complex natural product from natural sources. This work describes the development of a robust, scalable synthetic sequence relying on a convergent strategy that delivered a sufficient amount of the toxin for detailed biological studies and its commercialization for use by other research groups and regulatory agencies. A central transformation in the synthesis is the highly diastereoselective Ireland-Claisen rearrangement of a complex α,α-disubstituted allylic ester based on a unique mode for stereoselective enolization through a chirality match between the substrate and the lithium amide base. With synthetic pinnatoxin A, a detailed study has been performed that provides conclusive evidence for its mode of action as a potent inhibitor of nicotinic acetylcholine receptors selective for the human neuronal α7 subtype. The comprehensive electrophysiological, biochemical, and computational studies support the view that the spiroimine subunit of pinnatoxins is critical for blocking nicotinic acetylcholine receptor subtypes, as evidenced by analyzing the effect of a synthetic analogue of pinnatoxin A containing an open form of the imine ring. Our studies have paved the way for the production of certified standards to be used for mass-spectrometric determination of these toxins in marine matrices and for the development of tests to detect these toxins in contaminated shellfish. PMID:21644584

  9. Enantiospecific Total Synthesis of the Important Biogenetic Intermediates Along the Ajmaline Pathway, (+)-Polyneuridine and (+)-Polyneuridine Aldehyde, as well as 16-Epi-Vellosimine and Macusine A

    Science.gov (United States)

    Yin, Wenyuan; Kabir, M. Shahjahan; Wang, Zhijian; Rallapalli, Sundari K.; Ma, Jun; Cook, James M.

    2011-01-01

    The first stereospecific synthesis of polyneuridine aldehyde (6), 16-epi-vellosimine (7), (+)-polyneuridine (8), and (+)-macusine A (9) has been accomplished from commercially available D-(+)-tryptophan methyl ester. D-(+)-Tryptophan has served here both as the chiral auxiliary and the starting material for the synthesis of the common intermediate, (+)-vellosimine (13). This alkaloid was available in enantiospecific fashion in seven reaction vessels in 27% overall yield from D-(+)-trytophan methyl ester (14) via a combination of the asymmetric Pictet-Spengler reaction, Dieckmann cyclization, and a stereocontrolled intramolecular enolate-driven palladium-mediated cross-coupling reaction. A new process for this stereocontrolled intramolecular cross-coupling has been developed via a copper-mediated process. The initial results of this investigation indicated that an enolate driven palladium-mediated cross-coupling reaction can be accomplished by a copper-mediated process which is less expensive and much easier to work-up. An enantiospecific total synthesis of (+)-polyneuridine aldehyde (6), which has been proposed as an important biogenetic intermediate in the biosynthesis of quebrachidine (2), was then accomplished in an overall yield of 14.1% in 13 reaction vessels from D-(+)-tryptophan methyl ester (14). Aldehyde 13 was protected as the Na-Boc aldehyde 32 and then converted into the prochiral C (16)-quaternary diol 12 via the practical Tollens’ reaction and deprotection. The DDQ-mediated oxidative cyclization and TFA/Et3SiH reductive cleavage served as protection/deprotection steps to provide a versatile entry into the three alkaloids, polyneuridine aldehyde (6), polyneuridine (8) and macusine A (9) from the quarternary diol 12. The oxidation of the 16-hydroxymethyl group present in the axial position was achieved with the Corey-Kim reagent to provide the desired β-axial aldehydes, polyneuridine aldehyde (6) and 16-epi-vellosimine (7) with 100

  10. Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A.

    Science.gov (United States)

    Yin, Wenyuan; Kabir, M Shahjahan; Wang, Zhijian; Rallapalli, Sundari K; Ma, Jun; Cook, James M

    2010-05-21

    The first stereospecific synthesis of polyneuridine aldehyde (6), 16-epivellosimine (7), (+)-polyneuridine (8), and (+)-macusine A (9) has been accomplished from commercially available d-(+)-tryptophan methyl ester. d-(+)-Tryptophan has served here both as the chiral auxiliary and the starting material for the synthesis of the common intermediate, (+)-vellosimine (13). This alkaloid was available in enantiospecific fashion in seven reaction vessels in 27% overall yield from d-(+)-trytophan methyl ester (14) via a combination of the asymmetric Pictet-Spengler reaction, Dieckmann cyclization, and a stereocontrolled intramolecular enolate-driven palladium-mediated cross-coupling reaction. A new process for this stereocontrolled intramolecular cross-coupling has been developed via a copper-mediated process. The initial results of this investigation indicated that an enolate-driven palladium-mediated cross-coupling reaction can be accomplished by a copper-mediated process which is less expensive and much easier to work up. An enantiospecific total synthesis of (+)-polyneuridine aldehyde (6), which has been proposed as an important biogenetic intermediate in the biosynthesis of quebrachidine (2), was then accomplished in an overall yield of 14.1% in 13 reaction vessels from d-(+)-tryptophan methyl ester (14). Aldehyde 13 was protected as the N(a)-Boc aldehyde 32 and then converted into the prochiral C(16)-quaternary diol 12 via the practical Tollens' reaction and deprotection. The DDQ-mediated oxidative cyclization and TFA/Et(3)SiH reductive cleavage served as protection/deprotection steps to provide a versatile entry into the three alkaloids polyneuridine aldehyde (6), polyneuridine (8), and macusine A (9) from the quarternary diol 12. The oxidation of the 16-hydroxymethyl group present in the axial position was achieved with the Corey-Kim reagent to provide the desired beta-axial aldehydes, polyneuridine aldehyde (6), and 16-epivellosimine (7) with 100

  11. Total synthesis and biological evaluation of a series of macrocyclic hybrids and analogues of the antimitotic natural products dictyostatin, discodermolide, and taxol.

    Science.gov (United States)

    Paterson, Ian; Naylor, Guy J; Gardner, Nicola M; Guzmán, Esther; Wright, Amy E

    2011-02-01

    The design, synthesis, and biological evaluation of a series of hybrids and analogues of the microtubule-stabilizing anticancer agents dictyostatin, discodermolide, and taxol is described. A 22-membered macrolide scaffold was prepared by adapting earlier synthetic routes directed towards dictyostatin and discodermolide, taking advantage of the distinctive structural and stereochemical similarities between these two polyketide-derived marine natural products. Initial endeavors towards accessing novel discodermolide/dictyostatin hybrids led to the adoption of a late-stage diversification strategy and the construction of a small library of methyl-ether derivatives, along with the first triple hybrids bearing the side-chain of taxol or taxotere attached through an ester linkage. Biological assays of the anti-proliferative activity of these compounds in a series of human cancer cell lines, including the taxol-resistant NCI/ADR-Res cell line, allowed the proposal of various structure-activity relationships. This led to the identification of a potent macrocyclic discodermolide/dictyostatin hybrid 12 and its C9 methoxy derivative 38, accessible by an efficient total synthesis and with a similar biological profile to dictyostatin.

  12. Arg-Gly-Asp (RGD) Modified Biomimetic Polymeric Materials

    Institute of Scientific and Technical Information of China (English)

    Xufeng NIU; Yuanliang WANG; Yanfeng LUO; Juan XIN; Yonggang LI

    2005-01-01

    The new generation of biomaterials focuses on the design of biomimetic polymeric materials that are capable of eliciting specific cellular responses and directing new tissue formation. Since Arg-Gly-Asp (RGD) sequences have been found to promote cell adhesion in 1984, numerous polymers have been functionalized with RGD peptides for tissue engineering applications. This review gave the advance in RGD modified biomimetic polymeric materials,focusing on the mechanism of RGD, the surface and bulk modification of polymer with RGD peptides and the evaluation in vitro and in vivo of the modified biomimetic materials.

  13. Biomimetics as a design methodology – possibilities and challenges

    DEFF Research Database (Denmark)

    Lenau, Torben Anker

    2009-01-01

    Biomimetics – or bionik as it is called in parts of Europe – offer a number of promising opportunities and challenges for the designer. The paper investigates how biomimetics as a design methodology is used in engineering design by looking at examples of biological searches and highlight...... the possibilities and challenges. Biomimetics for engineering design is explored through an experiment involving 12 design engineering students. For 7 selected problem areas they searched biology literature available at a university library and identified a number of biological solutions. Central solution...

  14. Biomimetics applied to centering in micro-assembly

    DEFF Research Database (Denmark)

    Shu, L.H.; Lenau, Torben Anker; Hansen, Hans Nørgaard;

    2003-01-01

    This paper describes the application of a biomimetic search method to develop ideas for centering objects in micro-assembly. Biomimetics involves the imitation of biological phenomena to solve problems. An obstacle to the use of biomimetics in engineering is knowledge of biological phenomena...... that is relevant to the problem at hand. The method described here starts with an engineering problem, and then systematically searches for analogous biological phenomena using functional keywords. This method is illustrated by finding and using analogies for the problem of positioning and centering objects during...

  15. Biomimetic multifunctional surfaces inspired from animals.

    Science.gov (United States)

    Han, Zhiwu; Mu, Zhengzhi; Yin, Wei; Li, Wen; Niu, Shichao; Zhang, Junqiu; Ren, Luquan

    2016-08-01

    Over millions of years, animals have evolved to a higher intelligent level for their environment. A large number of diverse surface structures on their bodies have been formed to adapt to the extremely harsh environment. Just like the structural diversity existed in plants, the same also applies true in animals. Firstly, this article provides an overview and discussion of the most common functional surface structures inspired from animals, such as drag reduction, noise reduction, anti-adhesion, anti-wear, anti-erosion, anti-fog, water capture, and optical surfaces. Then, some typical characteristics of morphologies, structures, and materials of the animal multifunctional surfaces were discussed. The adaptation of these surfaces to environmental conditions was also analyzed. It mainly focuses on the relationship between their surface functions and their surface structural characteristics. Afterwards, the multifunctional mechanisms or principles of these surfaces were discussed. Models of these structures were provided for the development of structure materials and machinery surfaces. At last, fabrication techniques and existing or potential technical applications inspired from biomimetic multifunctional surfaces in animals were also discussed. The application prospects of the biomimetic functional surfaces are very broad, such as civil field of self-cleaning textile fabrics and non-stick pots, ocean field of oil-water separation, sports field of swimming suits, space development field of lens arrays. PMID:27085632

  16. Synthesis, structure and total conductivity of A-site doped LaTiO{sub 3−δ} perovskites

    Energy Technology Data Exchange (ETDEWEB)

    Bradha, M. [Nanotech Research Facility, PSG Institute of Advanced Studies, Coimbatore 641 004, TN (India); Hussain, S.; Chakravarty, Sujay [UGC-DAE CSR, Kalpakkam Node, Kokilamedu 603 104, TN (India); Amarendra, G. [UGC-DAE CSR, Kalpakkam Node, Kokilamedu 603 104, TN (India); Indira Gandhi Centre for Atomic Research, Kalpakkam 603 102, TN (India); Ashok, Anuradha, E-mail: anu.machina@gmail.com [Nanotech Research Facility, PSG Institute of Advanced Studies, Coimbatore 641 004, TN (India)

    2015-03-25

    Highlights: • A-site divalent alkaline earth metal doped LaTiO{sub 3−δ} perovskites were synthesised by sol–gel method. • Structural studies revealed no change in crystal symmetry but change in cell dimensions after doping. • After doping divalent cations in A-site, an enhancement in total conductivity was observed in LaTiO{sub 3−δ}. • Temperature dependent electrical property was observed in all synthesised perovskites. - Abstract: Oxygen deficient perovskites LaTiO{sub 3−δ} and La{sub 0.8}A{sub 0.2}TiO{sub 3−δ} (A = Ba, Sr, Ca) were synthesized by sol–gel method. The effect of divalent dopants on microstructure is investigated in detail using X-ray Diffraction (XRD) and Scanning Electron Microscopy (SEM). The oxidation states of La{sup 3+} and Ti{sup 3+} ions have been deduced using X-ray Photoelectron Spectroscopy (XPS). Impedance spectroscopy was used to analyze the total conductivity, an increase in conductivity was observed after doping in the A-site with divalent cations Ba, Ca and Sr. Among the investigated perovskites La{sub 0.8}Ca{sub 0.2}TiO{sub 3−δ} exhibited the maximum conductivity of 1.22 × 10{sup −2} S/cm in air atmosphere at 650 °C.

  17. Development of a third-generation total synthesis of (+)-discodermolide: an expedient Still-Gennari-type fragment coupling utilizing an advanced beta-ketophosphonate.

    Science.gov (United States)

    Paterson, Ian; Lyothier, Isabelle

    2005-07-01

    [structure: see text] A novel total synthesis of the complex polyketide discodermolide, a promising anticancer agent of marine sponge origin, has been completed in 11.1% overall yield over 21 linear steps. This third-generation approach features an unprecedented Still-Gennari-type HWE olefination reaction between advanced C1-C8 beta-ketophosphonate 61 and C9-C24 aldehyde 7, introducing the (8Z)-alkene with 10:1 selectivity. The stereotetrad found in the C1-C8 subunit 61 was established via a highly diastereoselective boron-mediated aldol reaction/in situ reduction between ketone (S)-8 and 3-benzyloxypropanal. The (7S)-configuration was installed by the reduction of enone 73 with K-Selectride.

  18. Autoradiographic studies on mucilage synthesis in Chara vulgaris antheridium with the use of 3H-fucose in total darkness and light

    International Nuclear Information System (INIS)

    Autoradiographic studies with 3H-fucose have shown that this precursor of polysaccharide compounds is incorporated into manubria and antheridial mucilage of Chara vulgaris both in the light and in the darkness. The dynamic of this process is lower in total darkness. The decrease in overall labelling of antheridium (manubria an mucilage) reflects secondary metabolic changes both in proliferative phase and in spermiogenesis. The pulse (2 and 5 min) incubations with the isotope confirm the intensive mucilage translocation which at later developmental stages is more dynamic than at earlier ones. It can explain previously observed decrease in manubria radioactivity at later stages after long (40 min) incubation, because PAS-positive polysaccharide synthesis is simultaneous with their fast translocation to the antheridial space. The present and previous autoradiographic and cytophotometric data taken altogether confirm the assumption about a nutritive role of mucilage filling Chara antheridium during the process of spermatogenesis. (author). 19 refs, 7 figs

  19. Autoradiographic studies on mucilage synthesis in Chara vulgaris antheridium with the use of {sup 3}H-fucose in total darkness and light

    Energy Technology Data Exchange (ETDEWEB)

    Gosek, A. [Lodz Univ. (Poland)

    1996-12-31

    Autoradiographic studies with {sup 3}H-fucose have shown that this precursor of polysaccharide compounds is incorporated into manubria and antheridial mucilage of Chara vulgaris both in the light and in the darkness. The dynamic of this process is lower in total darkness. The decrease in overall labelling of antheridium (manubria an mucilage) reflects secondary metabolic changes both in proliferative phase and in spermiogenesis. The pulse (2 and 5 min) incubations with the isotope confirm the intensive mucilage translocation which at later developmental stages is more dynamic than at earlier ones. It can explain previously observed decrease in manubria radioactivity at later stages after long (40 min) incubation, because PAS-positive polysaccharide synthesis is simultaneous with their fast translocation to the antheridial space. The present and previous autoradiographic and cytophotometric data taken altogether confirm the assumption about a nutritive role of mucilage filling Chara antheridium during the process of spermatogenesis. (author). 19 refs, 7 figs.

  20. Biomimetic autonomous robot inspired by the Cyanea capillata (Cyro)

    International Nuclear Information System (INIS)

    A biomimetic robot inspired by Cyanea capillata, termed as ‘Cyro’, was developed to meet the functional demands of underwater surveillance in defense and civilian applications. The vehicle was designed to mimic the morphology and swimming mechanism of the natural counterpart. The body of the vehicle consists of a rigid support structure with linear DC motors which actuate eight mechanical arms. The mechanical arms in conjunction with artificial mesoglea create the hydrodynamic force required for propulsion. The full vehicle measures 170 cm in diameter and has a total mass of 76 kg. An analytical model of the mechanical arm kinematics was developed. The analytical and experimental bell kinematics were analyzed and compared to the C. capillata. Cyro was found to reach the water surface untethered and autonomously from a depth of 182 cm in five actuation cycles. It achieved an average velocity of 8.47 cm s−1 while consuming an average power of 70 W. A two-axis thrust stand was developed to calculate the thrust directly from a single bell segment yielding an average thrust of 27.9 N for the whole vehicle. Steady state velocity during Cyro's swimming test was not reached but the measured performance during its last swim cycle resulted in a cost of transport of 10.9 J (kg ⋅ m)−1 and total efficiency of 0.03. (paper)

  1. Biomimetic autonomous robot inspired by the Cyanea capillata (Cyro).

    Science.gov (United States)

    Villanueva, Alex A; Marut, Kenneth J; Michael, Tyler; Priya, Shashank

    2013-12-01

    A biomimetic robot inspired by Cyanea capillata, termed as 'Cyro', was developed to meet the functional demands of underwater surveillance in defense and civilian applications. The vehicle was designed to mimic the morphology and swimming mechanism of the natural counterpart. The body of the vehicle consists of a rigid support structure with linear DC motors which actuate eight mechanical arms. The mechanical arms in conjunction with artificial mesoglea create the hydrodynamic force required for propulsion. The full vehicle measures 170 cm in diameter and has a total mass of 76 kg. An analytical model of the mechanical arm kinematics was developed. The analytical and experimental bell kinematics were analyzed and compared to the C. capillata. Cyro was found to reach the water surface untethered and autonomously from a depth of 182 cm in five actuation cycles. It achieved an average velocity of 8.47 cm s(-1) while consuming an average power of 70 W. A two-axis thrust stand was developed to calculate the thrust directly from a single bell segment yielding an average thrust of 27.9 N for the whole vehicle. Steady state velocity during Cyro's swimming test was not reached but the measured performance during its last swim cycle resulted in a cost of transport of 10.9 J (kg ⋅ m)(-1) and total efficiency of 0.03. PMID:24166747

  2. Total replacement of corn by mesquite pod meal considering nutritional value, performance, feeding behavior, nitrogen balance, and microbial protein synthesis of Holstein-Zebu crossbred dairy steers.

    Science.gov (United States)

    de Oliveira Moraes, Gláucia Sabrine; de Souza, Evaristo Jorge Oliveira; Véras, Antonia Sherlânea Chaves; de Paula Almeida, Marina; da Cunha, Márcio Vieira; Torres, Thaysa Rodrigues; da Silva, Camila Sousa; Pereira, Gerfesson Felipe Cavalcanti

    2016-10-01

    The objective of the present study to assess the effects of mesquite pod addition replacing corn (0, 250, 500, 750, and 1000 g/kg in the dry matter basis) on nutrient intake, animal performance, feeding behavior, nutrient digestibility, nitrogen balance, and microbial protein synthesis. Twenty-five Holstein-Zebu crossbred dairy steers at 219 ± 22 kg initial body weight and 18 months of age were used. The experiment lasted 84 days, divided into three periods of 28 days. A completely randomized design was used, and data were submitted to analysis using PROC GLM for analysis of variance and PROC REG for regression analysis using the software Statistical Analysis Systems version 9.1. Experimental diets were composed of Tifton 85 hay, soybean meal, ground corn, mesquite pod meal, and mineral salt. Samples of food offered were collected during the last 3 days of each period, and the leftovers were collected daily, with samples bulked per week. At the end of each 28-day period, the remaining animals were weighed to determine total weight gain and average daily gain. The assessment of behavioral patterns was performed through instantaneous scans in 5-min intervals for three consecutive 12-h days. A single urine sample from each animal was collected on the last day of each collection period at about 4 h after the first feeding. The replacement of corn by mesquite pod meal did not significantly influence treatments regarding nutrients intake, animal performance, and feeding behavior. Retained and consumed nitrogen ratio did not statistically differ between replacement levels. Likewise, there were no statistical differences regarding microbial protein synthesis and efficiency between replacement levels. Mesquite pod meal can be used in Holstein-Zebu crossbred dairy steers' diet with total corn replacement. PMID:27387896

  3. Biomimetic synthesized chiral mesoporous silica: Structures and controlled release functions as drug carrier

    International Nuclear Information System (INIS)

    This work initially illustrated the formation mechanism of chiral mesoporous silica (CMS) in a brand new insight named biomimetic synthesis. Three kinds of biomimetic synthesized CMS (B-CMS, including B-CMS1, B-CMS2 and B-CMS3) were prepared using different pH or stirring rate condition, and their characteristics were tested with transmission electron microscope and small angle X-ray diffraction. The model drug indomethacin was loaded into B-CMS and drug loading content was measured using ultraviolet spectroscopy. The result suggested that pH condition influenced energetics of self-assembly process, mainly packing energetics of the surfactant, while stirring rate was the more dominant factor to determine particle length. In application, indomethacin loading content was measured to be 35.3%, 34.8% and 35.1% for indomethacin loaded B-CMS1, indomethacin loaded B-CMS2 and indomethacin loaded B-CMS3. After loading indomethacin into B-CMS carriers, surface area, pore volume and pore diameter of B-CMS carriers were reduced. B-CMS converted crystalline state of indomethacin to amorphous state, leading to the improved indomethacin dissolution. B-CMS1 controlled drug release without burst-release, while B-CMS2 and B-CMS3 released indomethacin faster than B-CMS1, demonstrating that the particle length, the ordered lever of multiple helixes, the curvature degree of helical channels and pore diameter greatly contributed to the release behavior of indomethacin loaded B-CMS. - Highlights: • Chiral mesoporous silica was synthesized using biomimetic method. • pH influenced energetics of self-assembly process of chiral mesoporous silica. • Stirring rate determined the particle length of chiral mesoporous silica. • Controlled release behaviors of chiral mesoporous silica varied based on structures

  4. Biomimetic synthesized chiral mesoporous silica: Structures and controlled release functions as drug carrier

    Energy Technology Data Exchange (ETDEWEB)

    Li, Jing; Xu, Lu, E-mail: xl2013109@163.com; Yang, Baixue; Bao, Zhihong; Pan, Weisan; Li, Sanming, E-mail: li_sanming2013@163.com

    2015-10-01

    This work initially illustrated the formation mechanism of chiral mesoporous silica (CMS) in a brand new insight named biomimetic synthesis. Three kinds of biomimetic synthesized CMS (B-CMS, including B-CMS1, B-CMS2 and B-CMS3) were prepared using different pH or stirring rate condition, and their characteristics were tested with transmission electron microscope and small angle X-ray diffraction. The model drug indomethacin was loaded into B-CMS and drug loading content was measured using ultraviolet spectroscopy. The result suggested that pH condition influenced energetics of self-assembly process, mainly packing energetics of the surfactant, while stirring rate was the more dominant factor to determine particle length. In application, indomethacin loading content was measured to be 35.3%, 34.8% and 35.1% for indomethacin loaded B-CMS1, indomethacin loaded B-CMS2 and indomethacin loaded B-CMS3. After loading indomethacin into B-CMS carriers, surface area, pore volume and pore diameter of B-CMS carriers were reduced. B-CMS converted crystalline state of indomethacin to amorphous state, leading to the improved indomethacin dissolution. B-CMS1 controlled drug release without burst-release, while B-CMS2 and B-CMS3 released indomethacin faster than B-CMS1, demonstrating that the particle length, the ordered lever of multiple helixes, the curvature degree of helical channels and pore diameter greatly contributed to the release behavior of indomethacin loaded B-CMS. - Highlights: • Chiral mesoporous silica was synthesized using biomimetic method. • pH influenced energetics of self-assembly process of chiral mesoporous silica. • Stirring rate determined the particle length of chiral mesoporous silica. • Controlled release behaviors of chiral mesoporous silica varied based on structures.

  5. Biomimetics materials, structures and processes : examples, ideas and case studies

    CERN Document Server

    Bruckner, Dietmar; Hellmich, Christian; Schmiedmayer, Heinz-Bodo; Stachelberger, Herbert; Gebeshuber, Ille

    2011-01-01

    The book presents an outline of current activities in the field of biomimetics and integrates a variety of applications comprising biophysics, surface sciences, architecture and medicine. Biomimetics as innovation method is characterised by interdisciplinary information transfer from the life sciences to technical application fields aiming at increased performance, functionality and energy efficiency. The contributions of the book relate to the research areas: - Materials and structures in nanotechnology and biomaterials - Biomimetic approaches to develop new forms, construction principles and design methods in architecture - Information and dynamics in automation, neuroinformatics and biomechanics Readers will be informed about the latest research approaches and results in biomimetics with examples ranging from bionic nano-membranes to function-targeted design of tribological surfaces and the translation of natural auditory coding strategies.

  6. A review paper on biomimetic calcium phosphate coatings

    OpenAIRE

    Lin, X.; De Groot,, P.A.J.; Wang, D.; Hu, Q; Wismeijer, D.; Liu, Y

    2015-01-01

    Biomimetic calcium phosphate coatings have been developed for bone regeneration and repair because of their biocompatibility, osteoconductivity, and easy preparation. They can be rendered osteoinductive by incorporating an osteogenic agent, such as bone morphogenetic protein 2 (BMP-2), into the crystalline lattice work in physiological situations. The biomimetic calcium phosphate coating enables a controlled, slow and local release of BMP-2 when it undergoes cell mediated coating degradation ...

  7. Stability of biomimetic ferrofluids established by a systematic study using microwave irradiation at defined wattages

    Energy Technology Data Exchange (ETDEWEB)

    Bhattacharya, Soumya, E-mail: soumya_524@yahoo.in [Materials Science and Technology Division, National Metallurgical Laboratory, Council of Scientific and Industrial Research, Jamshedpur 831007 (India); Jenamoni, Krishna [Department of Biotechnology, Amity University, Sector-125, Noida 201303 (India); Nayar, Suprabha [Materials Science and Technology Division, National Metallurgical Laboratory, Council of Scientific and Industrial Research, Jamshedpur 831007 (India)

    2012-10-15

    An established biomimetic process for the synthesis of aqueous ferrofluids using polymers has been subjected to systematic microwave irradiation at different wattages primarily to see if the magnetization could be increased by microwave irradiation and if so how would it affect the stability of the fluid. Care has been taken to maintain ambient conditions of synthesis even after three cycles of microwave irradiation before oxidation and ten cycles after it, so as not to violate the basic principles of the process. Detailed characterization using, x-ray diffractometry, transmission electron microscopy, fourier transform infra-red spectroscopy, dynamic light scattering, thermo-gravimetric analysis, differential thermal analysis and vibrating sample magnetometry showed that these fluids containing iron oxide nanoparticles-poly(vinyl) alcohol nanocomposites are highly stable in the proportions established by us. Measurements at five different wattages double the saturation magnetization but the stability remains unaffected compared to the one without microwave irradiation, forcing us to believe that the incubation of the iron salt solution and the polymer in the right proportion before oxidation is what contributes to the stability and that increasing the number of cycles of microwave irradiation at this stage, perhaps, would have led to a more pronounced effect. - Highlights: Black-Right-Pointing-Pointer Single step biomimetic synthesis of aqueous ferrofluids. Black-Right-Pointing-Pointer Role of polyvinyl alcohol as a surfactant and as a template for nucleation and growth of iron oxide nanoparticles. Black-Right-Pointing-Pointer Heat treatment by microwave irradiation in a systematic and periodic manner. Black-Right-Pointing-Pointer High colloidal stability. Black-Right-Pointing-Pointer Increase in saturation magnetization with increasing wattage.

  8. Biomimetic mineral coatings in dental and orthopaedic implantology

    Institute of Scientific and Technical Information of China (English)

    Yue-lian LIU; Klaas de GROOT; Ernst B.HUNZIKER

    2009-01-01

    Biomimetic techniques are used to deposit coatings of calcium phosphate upon medical devices. The procedure is conducted under near-physiological, or "biomimetic", conditions of temperature and pH primarily to improve their biocompatibility and biodegradability of the materials. The inorganic layers genelated by biomi-metic methods resemble bone mineral, and can be degraded within a biological milieu.The biomimetic coating technique involves the nuclea-tion and growth of bone-like crystals upon a pretreated substrate by immersing this in a supersaturated solution of calcium phosphate under physiological conditions of temperature (37~C) and pH (7.4). The method, originally developed by Kokubo in 1990, has since undergone improvement and refinement by several groups of investigators.Biomimetic coatings are valuable in that they can serve as a vehicle for the slow and sustained release of osteogenic agents at the site of implantation. This attribute is rendered possible by the near-physiological conditions under which these coatings are prepared, which permits an incorporation of binactive agents into the inorganic crystal latticework rather than their nlere superficial adsorption onto preformed layers. In addition, the biomimetic coating technique can be applied to implants of an organic as well as of an inorganic nature and to those with irregular surface geometries, which is not possible using conventional methodologies.

  9. Sensing in nature: using biomimetics for design of sensors

    DEFF Research Database (Denmark)

    Lenau, Torben Anker; Cheong, Hyunmin; Shu, Li

    2010-01-01

    The paper illustrates how biomimetics can be applied in sensor design. Biomimetics is an engineering discipline that uses nature as an inspiration source for generating ideas for how to solve engineering problems. Using biomimetics involves a search for relevant cases, a proper analysis of the bi......The paper illustrates how biomimetics can be applied in sensor design. Biomimetics is an engineering discipline that uses nature as an inspiration source for generating ideas for how to solve engineering problems. Using biomimetics involves a search for relevant cases, a proper analysis...... of the biological solutions, identification of design principles and design of the desired artefact. We use a search method developed at University of Toronto. It is based on formulation of relevant keywords and search for occurrences in a standard university biology textbook. Most often a simple formulation...... of keywords and a following search is not enough to generate a sufficient amount of useful ideas or the search gives to many results. This is handled by a more advanced search strategy where the search is either widened or it is focused further mainly using biological synonyms. The paper also reviews a number...

  10. Greener Biomimetic Approach to the Synthesis of Nanomaterials and Nanocomposite

    Science.gov (United States)

    A brief account of greener production of nanoparticles which reduces or eliminates the use and generation of hazardous substances is presented. The utility of vitamins B1 and B2, which can function both as reducing and capping agents, provides an extremely simple, one-pot, greene...

  11. Combinatorial microfluidic droplet engineering for biomimetic material synthesis

    Science.gov (United States)

    Bawazer, Lukmaan A.; McNally, Ciara S.; Empson, Christopher J.; Marchant, William J.; Comyn, Tim P.; Niu, Xize; Cho, Soongwon; McPherson, Michael J.; Binks, Bernard P.; deMello, Andrew; Meldrum, Fiona C.

    2016-01-01

    Although droplet-based systems are used in a wide range of technologies, opportunities for systematically customizing their interface chemistries remain relatively unexplored. This article describes a new microfluidic strategy for rapidly tailoring emulsion droplet compositions and properties. The approach uses a simple platform for screening arrays of droplet-based microfluidic devices and couples this with combinatorial selection of the droplet compositions. Through the application of genetic algorithms over multiple screening rounds, droplets with target properties can be rapidly generated. The potential of this method is demonstrated by creating droplets with enhanced stability, where this is achieved by selecting carrier fluid chemistries that promote titanium dioxide formation at the droplet interfaces. The interface is a mixture of amorphous and crystalline phases, and the resulting composite droplets are biocompatible, supporting in vitro protein expression in their interiors. This general strategy will find widespread application in advancing emulsion properties for use in chemistry, biology, materials, and medicine.

  12. Clues for biomimetics from natural composite materials

    Science.gov (United States)

    Lapidot, Shaul; Meirovitch, Sigal; Sharon, Sigal; Heyman, Arnon; Kaplan, David L; Shoseyov, Oded

    2013-01-01

    Bio-inspired material systems are derived from different living organisms such as plants, arthropods, mammals and marine organisms. These biomaterial systems from nature are always present in the form of composites, with molecular-scale interactions optimized to direct functional features. With interest in replacing synthetic materials with natural materials due to biocompatibility, sustainability and green chemistry issues, it is important to understand the molecular structure and chemistry of the raw component materials to also learn from their natural engineering, interfaces and interactions leading to durable and highly functional material architectures. This review will focus on applications of biomaterials in single material forms, as well as biomimetic composites inspired by natural organizational features. Examples of different natural composite systems will be described, followed by implementation of the principles underlying their composite organization into artificial bio-inspired systems for materials with new functional features for future medicine. PMID:22994958

  13. Biomimetic electrospun nanofibers for tissue regeneration

    Energy Technology Data Exchange (ETDEWEB)

    Liao, Susan; Li Bojun; Ma Zuwei; Wei He; Chan Casey; Ramakrishna, Seeram [Nanoscience and Nanotechnology Initiative (NUSNNI), Faculty of Engineering, National University of Singapore, 117576 Singapore (Singapore)

    2006-09-15

    Nanofibers exist widely in human tissue with different patterns. Electrospinning nanotechnology has recently gained a new impetus due to the introduction of the concept of biomimetic nanofibers for tissue regeneration. The advanced electrospinning technique is a promising method to fabricate a controllable continuous nanofiber scaffold similar to the natural extracellular matrix. Thus, the biomedical field has become a significant possible application field of electrospun fibers. Although electrospinning has developed rapidly over the past few years, electrospun nanofibers are still at a premature research stage. Further comprehensive and deep studies on electrospun nanofibers are essential for promoting their biomedical applications. Current electrospun fiber materials include natural polymers, synthetic polymers and inorganic substances. This review briefly describes several typically electrospun nanofiber materials or composites that have great potential for tissue regeneration, and describes their fabrication, advantages, drawbacks and future prospects. (topical review)

  14. Progress of Biomimetic Artificial Nose and Tongue

    Science.gov (United States)

    Wang, Ping; Liu, Qingjun

    2009-05-01

    As two of the basic senses of human beings, olfaction and gustation play a very important role in daily life. These two types of chemical sensors are important for recognizing environmental conditions. Electronic nose and electronic tongue, which mimics animals' olfaction and gustation to detect odors and chemical components, have been carried out due to their potential commercial applications for biomedicine, food industry and environmental protection. In this report, the biomimetic artificial nose and tongue is presented. Firstly, the smell and taste sensors mimicking the mammalian olfaction and gustation was described, and then, some mimetic design of electronic nose and tongue for odorants and tastants detection are developed. Finally, olfactory and gustatory biosensors are presented as the developing trends of this field.

  15. Biomimetic Hybrid Nanocontainers with Selective Permeability.

    Science.gov (United States)

    Messager, Lea; Burns, Jonathan R; Kim, Jungyeon; Cecchin, Denis; Hindley, James; Pyne, Alice L B; Gaitzsch, Jens; Battaglia, Giuseppe; Howorka, Stefan

    2016-09-01

    Chemistry plays a crucial role in creating synthetic analogues of biomacromolecular structures. Of particular scientific and technological interest are biomimetic vesicles that are inspired by natural membrane compartments and organelles but avoid their drawbacks, such as membrane instability and limited control over cargo transport across the boundaries. In this study, completely synthetic vesicles were developed from stable polymeric walls and easy-to-engineer membrane DNA nanopores. The hybrid nanocontainers feature selective permeability and permit the transport of organic molecules of 1.5 nm size. Larger enzymes (ca. 5 nm) can be encapsulated and retained within the vesicles yet remain catalytically active. The hybrid structures constitute a new type of enzymatic nanoreactor. The high tunability of the polymeric vesicles and DNA pores will be key in tailoring the nanocontainers for applications in drug delivery, bioimaging, biocatalysis, and cell mimicry. PMID:27560310

  16. Electrochemical characterization of hydrogels for biomimetic applications

    DEFF Research Database (Denmark)

    Peláez, L.; Romero, V.; Escalera, S.;

    2011-01-01

    ) or a photoinitiator (P) to encapsulate and stabilize biomimetic membranes for novel separation technologies or biosensor applications. In this paper, we have investigated the electrochemical properties of the hydrogels used for membrane encapsulation. Specifically, we studied the crosslinked hydrogels by using...... electrochemical impedance spectroscopy (EIS), and we demonstrated that chemically crosslinked hydrogels had lower values for the effective electrical resistance and higher values for the electrical capacitance compared with hydrogels with photoinitiated crosslinking. Transport numbers were obtained using......〉 and 〈Pw〉 values than PEG‐1000‐DMA‐P and PEG‐400‐DA‐P hydrogels. In conclusion, our results show that hydrogel electrochemical properties can be controlled by the choice of polymer and type of crosslinking used and that their water and salt permeability properties are congruent with the use of hydrogels...

  17. Biomimetic Membrane Arrays on Cast Hydrogel Supports

    DEFF Research Database (Denmark)

    Roerdink-Lander, Monique; Ibragimova, Sania; Rein Hansen, Christian;

    2011-01-01

    , provides mechanical support but at the cost of small molecule transport through the membrane−support sandwich. To stabilize biomimetic membranes while allowing transport through a membrane−support sandwich, we have investigated the feasibility of using an ethylene tetrafluoroethylene (ETFE)/hydrogel...... sandwich as the support. The sandwich is realized as a perforated surface-treated ETFE film onto which a hydrogel composite support structure is cast. We report a simple method to prepare arrays of lipid bilayer membranes with low intrinsic electrical conductance on the highly permeable, self......-supporting ETFE/hydrogel sandwiches. We demonstrate how the ETFE/hydrogel sandwich support promotes rapid self-thinning of lipid bilayers suitable for hosting membrane-spanning proteins....

  18. Biomimetics for architecture & design nature, analogies, technology

    CERN Document Server

    Pohl, Göran

    2015-01-01

    This book provides the readers with a timely guide to the application of biomimetic principles in architecture and engineering design. As a result of a combined effort by two internationally recognized authorities, the biologist Werner Nachtigall and the architect Göran Pohl, the book describes the principles which can be used to compare nature and technology, and at the same time it presents detailed explanations and examples showing how biology can be used as a source of inspiration and “translated” in building and architectural solutions (biomimicry). Even though nature cannot be directly copied, the living world can provide architects and engineers with a wealth of analogues and inspirations for their own creative designs. But how can analysis of natural entities give rise to advanced and sustainable design? By reporting on the latest bionic design methods and using extensive artwork, the book guides readers through the field of nature-inspired architecture, offering an extraordinary resource for pro...

  19. Development of a Biomimetic Quadruped Robot

    Institute of Scientific and Technical Information of China (English)

    Thanhtam Ho; Sunghac Choi; Sangyoon Lee

    2007-01-01

    This paper presents the design and prototype of a small quadruped robot whose walking motion is realized by two piezocomposite actuators. In the design, biomimetic ideas are employed to obtain the agility of motions and sustainability of a heavy load. The design of the robot legs is inspired by the leg configuration of insects, two joints (hip and knee) of the leg enable two basic motions, lifting and stepping. The robot frame is designed to have a slope relative to the horizontal plane, which makes the robot move forward. In addition, the bounding locomotion of quadruped animals is implemented in the robot. Experiments show that the robot can carry an additional load of about 100 g and run with a fairly high velocity. The quadruped prototype can be an important step towards the goal of building an autonomous mobile robot actuated by piezocomposite actuators.

  20. Biomimetic artificial sphincter muscles: status and challenges

    Science.gov (United States)

    Leung, Vanessa; Fattorini, Elisa; Karapetkova, Maria; Osmani, Bekim; Töpper, Tino; Weiss, Florian; Müller, Bert

    2016-04-01

    Fecal incontinence is the involuntary loss of bowel content and affects more than 12% of the adult population, including 45% of retirement home residents. Severe fecal incontinence is often treated by implanting an artificial sphincter. Currently available implants, however, have long-term reoperation rates of 95% and definitive explantation rates of 40%. These statistics show that the implants fail to reproduce the capabilities of the natural sphincter and that the development of an adaptive, biologically inspired implant is required. Dielectric elastomer actuators (DEA) are being developed as artificial muscles for a biomimetic sphincter, due to their suitable response time, reaction forces, and energy consumption. However, at present the operation voltage of DEAs is too high for artificial muscles implanted in the human body. To reduce the operating voltage to tens of volts, we are using microfabrication to reduce the thickness of the elastomer layer to the nanometer level. Two microfabrication methods are being investigated: molecular beam deposition and electrospray deposition. This communication covers the current status and a perspective on the way forward, including the long-term prospects of constructing a smart sphincter from low-voltage sensors and actuators based on nanometer-thin dielectric elastomer films. As DEA can also provide sensory feedback, a biomimetic sphincter can be designed in accordance with the geometrical and mechanical parameters of its natural counterpart. The availability of such technology will enable fast pressure adaption comparable to the natural feedback mechanism, so that tissue atrophy and erosion can be avoided while maintaining continence du ring daily activities.

  1. Biomimetic oral mucin from polymer micelle networks

    Science.gov (United States)

    Authimoolam, Sundar Prasanth

    Mucin networks are formed by the complexation of bottlebrush-like mucin glycoprotein with other small molecule glycoproteins. These glycoproteins create nanoscale strands that then arrange into a nanoporous mesh. These networks play an important role in ensuring surface hydration, lubricity and barrier protection. In order to understand the functional behavior in mucin networks, it is important to decouple their chemical and physical effects responsible for generating the fundamental property-function relationship. To achieve this goal, we propose to develop a synthetic biomimetic mucin using a layer-by-layer (LBL) deposition approach. In this work, a hierarchical 3-dimensional structures resembling natural mucin networks was generated using affinity-based interactions on synthetic and biological surfaces. Unlike conventional polyelectrolyte-based LBL methods, pre-assembled biotin-functionalized filamentous (worm-like) micelles was utilized as the network building block, which from complementary additions of streptavidin generated synthetic networks of desired thickness. The biomimetic nature in those synthetic networks are studied by evaluating its structural and bio-functional properties. Structurally, synthetic networks formed a nanoporous mesh. The networks demonstrated excellent surface hydration property and were able capable of microbial capture. Those functional properties are akin to that of natural mucin networks. Further, the role of synthetic mucin as a drug delivery vehicle, capable of providing localized and tunable release was demonstrated. By incorporating antibacterial curcumin drug loading within synthetic networks, bacterial growth inhibition was also demonstrated. Thus, such bioactive interfaces can serve as a model for independently characterizing mucin network properties and through its role as a drug carrier vehicle it presents exciting future opportunities for localized drug delivery, in regenerative applications and as bio

  2. Biomimetic synthesized bimodal nanoporous silica: Bimodal mesostructure formation and application for ibuprofen delivery.

    Science.gov (United States)

    Li, Jing; Xu, Lu; Zheng, Nan; Wang, Hongyu; Lu, Fangzheng; Li, Sanming

    2016-01-01

    The present paper innovatively reports bimodal nanoporous silica synthesized using biomimetic method (B-BNS) with synthesized polymer (C16-L-serine) as template. Formation mechanism of B-BNS was deeply studied and exploration of its application as carrier of poorly water-soluble drug ibuprofen (IBU) was conducted. The bimodal nanopores and curved mesoscopic channels of B-BNS were achieved due to the dynamic self-assembly of C16-L-serine induced by silane coupling agent (3-aminopropyltriethoxysilane, APTES) and silica source (tetraethoxysilane, TEOS). Characterization results confirmed the successful synthesis of B-BNS, and particularly, nitrogen adsorption/desorption measurement demonstrated that B-BNS was meso-meso porous silica material. In application, B-BNS loaded IBU with high drug loading content due to its enlarged nanopores. After being loaded, IBU presented amorphous phase because nanoporous space and curved mesoscopic channels of B-BNS prevented the crystallization of IBU. In vitro release result revealed that B-BNS controlled IBU release with two release phases based on bimodal nanopores and improved dissolution in simulated gastric fluid due to crystalline conversion of IBU. It is convincible that biomimetic method provides novel theory and insight for synthesizing bimodal nanoporous silica, and unique functionalities of B-BNS as drug carrier can undoubtedly promote the application of bimodal nanoporous silica and development of pharmaceutical science.

  3. Design of biomimetic and bioactive cold plasma-modified nanostructured scaffolds for enhanced osteogenic differentiation of bone marrow-derived mesenchymal stem cells.

    Science.gov (United States)

    Wang, Mian; Cheng, Xiaoqian; Zhu, Wei; Holmes, Benjamin; Keidar, Michael; Zhang, Lijie Grace

    2014-03-01

    The objective of this study was to design a biomimetic and bioactive tissue-engineered bone construct via a cold atmospheric plasma (CAP) treatment for directed osteogenic differentiation of human bone morrow mesenchymal stem cells (MSCs). Porous nanocrystalline hydroxyapatite/chitosan scaffolds were fabricated via a lyophilization procedure. The nanostructured bone scaffolds were then treated with CAP to create a more favorable surface for cell attachment, proliferation, and differentiation. The CAP-modified scaffolds were characterized via scanning electron microscope, Raman spectrometer, contact angle analyzer, and white light interferometer. In addition, optimal CAP treatment conditions were determined. Our in vitro study shows that MSC adhesion and infiltration were significantly enhanced on CAP modified scaffolds. More importantly, it was demonstrated that CAP-modified nanostructured bone constructs can greatly promote total protein, collagen synthesis, and calcium deposition after 3 weeks of culture, thus making them a promising implantable scaffold for bone regeneration. Moreover, the fibronectin and vitronection adsorption experiments by enzyme-linked immunosorbent assay demonstrated that more adhesion-mediated protein adsorption on the CAP-treated scaffolds. Since the initial specific protein absorption on scaffold surfaces can lead to further recruitment as well as activation of favorable cell functions, it is suggested that our enhanced stem cell growth and osteogenic function may be related to more protein adsorption resulting from surface roughness and wettability modification. The CAP modification method used in this study provides a quick one-step process for cell-favorable tissue-engineered scaffold architecture remodeling and surface property alteration.

  4. Design and Dynamic Analysis of a Novel Biomimetic Robotics Hip Joint

    OpenAIRE

    Bingyan Cui; Liwen Chen; Zhijun Wang; Yuanhao Zhao; Zhanxian Li; Zhenlin Jin

    2015-01-01

    In order to increase the workspace and the carrying capacity of biomimetic robotics hip joint, a novel biomimetic robotics hip joint was developed. The biomimetic robotics hip joint is mainly composed of a moving platform, frame, and 3-RRR orthogonal spherical parallel mechanism branched chains, and has the characteristics of compact structure, large bearing capacity, high positioning accuracy, and good controllability. The functions of the biomimetic robotics hip joint are introduced, such a...

  5. Stereoselective total synthesis of sphingolipids

    Indian Academy of Sciences (India)

    PARAMESH JANGILI; PERLA RAMESH; BISWANATH DAS

    2016-11-01

    A novel sphingosine, 1,2-diacetyl D-erythro-sphinganine having a characteristic almond flavour was isolated from the edible mushroom Grifola gargal. We have synthesized this sphinganine along with the three other sphingolipids, such as 1,2-diacetyl L-threo-sphinganine, D-erythro-sphinganine triacetateand L-threo-sphinganine triacetate using Garner aldehyde as the starting material involving the Grignard reaction and Mitsunobu inversion. The sphingolipids 1,2-diacetyl D-erythro-sphinganine and 1,2-diacetyl L-threo-sphinganine have been synthesized for the first time.

  6. Total synthesis of (-)- and (+)-tedanalactam

    Digital Repository Service at National Institute of Oceanography (India)

    Majik, M.S.; Parameswaran, P.S.; Tilve, S.G.

    are given in Hz. Chiral HPLC analyses was executed using Jasco HPLC model MX-2080-31 instrument. tert-Butyl (3-hydroxypropyl)carbamate (10): The Boc 2 O (5.83 g, 0.026 mol) was added drop wise to a stirred solution of 3-amino-1-propanol 9 (1.744 g, 0... were recorded on a MicroMass ES- QTOF. Chiral HPLC analysis was executed using Jasco HPLC model MX-2080-31 instrument. Melting points were recorded using Thiele apparatus and are uncorrected. S2 2. Copies of 1 H NMR, 13 C NMR and DEPT...

  7. Total Synthesis of Securinega Alkaloids

    Institute of Scientific and Technical Information of China (English)

    T. Honda

    2005-01-01

    @@ 1Introduction Naturally occurring Securinega alkaloids (1-4) (Fig. 1)[1], with their wide range of structural and stereochemical features, continue to provide challenging synthetic targets, since these alkaloids exhibit attractive biological activities. Securinine (1), isolated from Securinega suffruticosa [2], was structurally determined to contain an indolizidine skeleton with an azabicyclo[3.2.1 ]octane system together with an α, β-unsaturated γ-lactone ring. This alkaloid has been clinically used in Russia as a CNS stimulating drug[3], and has been shown to act as a stereospecific antagonist at the GABA binding site of the GABAA-receptor complex[4].Viroallosecurinine (2), a diastereoisomeric alkaloid of securinine, was also isolated from the leaves of Securinega virosa[5] as a cytotoxic alkaloid exhibiting a MIC of 0.48 μg/mL for Ps. aeruginosa and Staph.aureus[6]. This alkaloid is recognized to be bactericidal since the yields of MIC/MBC were less than 1[7].

  8. Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

    Science.gov (United States)

    Schleicher, Kristin D; Sasaki, Yoshikazu; Tam, Annie; Kato, Daisuke; Duncan, Katharine K; Boger, Dale L

    2013-01-24

    The total synthesis of a systematic series of vinblastine analogues that contain deep-seated structural modifications to the core ring system of the lower vindoline subunit is described. Complementary to the vindoline 6,5 DE ring system, compounds with 5,5, 6,6, and the reversed 5,6 membered DE ring systems were prepared. Both the natural cis and unnatural trans 6,6-membered ring systems proved accessible, with the latter representing a surprisingly effective class for analogue design. Following Fe(III)-promoted coupling with catharanthine and in situ oxidation to provide the corresponding vinblastine analogues, their evaluation provided unanticipated insights into how the structure of the vindoline subunit contributes to activity. Two potent analogues (81 and 44) possessing two different unprecedented modifications to the vindoline subunit core architecture were discovered that matched the potency of the comparison natural products and both lack the 6,7-double bond whose removal in vinblastine leads to a 100-fold drop in activity.

  9. Total synthesis and in vitro bioevaluation of clavaminols A, C, H & deacetyl clavaminol H as potential chemotherapeutic and antibiofilm agents.

    Science.gov (United States)

    Vijai Kumar Reddy, T; Jyotsna, A; Prabhavathi Devi, B L A; Prasad, R B N; Poornachandra, Y; Ganesh Kumar, C

    2016-09-14

    A highly concise and expedient total synthesis of bioactive clavaminols (1-4) has been executed using commercially available achiral compound decanol. The synthetic strategy relied on trans-Wittig olefination, Sharpless asymmetric epoxidation, regioselective azidolysis and in situ detosylation followed by reduction as key reactions with good overall yield. Based on biological evaluation studies of all the synthesized compounds, it was observed that the clavaminol A (1) exhibited good cytotoxicity against DU145 and SKOV3 cell lines with IC50 value of 10.8 and 12.5 μM, respectively. Clavaminol A (1) and deacetyl clavaminol H (3) displayed selective promising inhibition towards Gram-positive pathogenic bacterial strains and showed good antifungal activity against the tested Candida strains. In addition, compounds 1 and 3 have demonstrated significant bactericidal activity. Compound 3 was found to be equipotent to the standard drug Miconazole displaying MFC value of 15.6 μg/mL against Candida albicans MTCC 854, C. albicans MTCC 1637, C. albicans MTCC 3958 and Candida glabrata MTCC 3019. Compounds 1 and 3 were also able to inhibit the biofilm formation of Micrococcus luteus MTCC 2470 and Staphylococcus aureus MLS16 MTCC 2940. Clavaminol A (1) increased the levels of reactive oxygen species (ROS) accumulation in M. luteus MTCC 2470. PMID:27187861

  10. Part 1. Approaches to the total synthesis of the diterpene marrubin. Part II. Ligand assisted nucleophilic additions. Part III. Coal processing in a non-dissolving medium

    Energy Technology Data Exchange (ETDEWEB)

    Lipscombe, J.; Charles, W. II

    1987-01-01

    The total synthesis of the diterpene marrubiin was attempted using methodology previously developed in the Liotta laboratories. Ligand Assisted Nucleophilic Additions (LANA) comprise a new class of synthetic reactions involving the stereoselective addition of some group, usually in an intramolecular conjugate fashion. This group is itself derived from an earlier nucleophilic addition to a carbonyl moiety. Exchange of the original metal of the alkoxide with a second metal (which must be at least divalent) having a transferrable group demands that the stereochemistry of the first addition control the second. The general features of these types of processes are discussed. Initial work with substituted quinones is presented, and some mechanistic rationales are given. A novel method of coal processing at modest temperatures and hydrogen pressures (250-300/sup 0/C, 8.0 MPa) is discussed. Coals reacted with small amounts of tetrahydroquinoline in the presence of fluorocarbons or other non-dissolving media underwent astounding increases in pyridine solubility, a common standard in coal liquefaction studies. Several additives were employed, although only tetrahydroquinoline was found to effectively increase coal solubility. Coals having vastly different individual properties behaved similarly under these conditions. Kinetic and model studies were used in an attempt to clarify the reactions occurring under these novel conditions.

  11. Biomimetic Preparation and Dual-Color Bioimaging of Fluorescent Silicon Nanoparticles.

    Science.gov (United States)

    Wu, Sicong; Zhong, Yiling; Zhou, Yanfeng; Song, Bin; Chu, Binbin; Ji, Xiaoyuan; Wu, Yanyan; Su, Yuanyuan; He, Yao

    2015-11-25

    Fluorescent silicon nanoparticles (SiNPs), as the most important zero-dimensional silicon nanostructures, hold high promise for long-awaited silicon-based optic applications. There currently remain major challenges for the green, inexpensive, and mass production of fluorescent SiNPs, resulting in difficulties in sufficiently exploiting the properties of these remarkable materials. Here, we show that fluorescent small-sized (∼3.8 nm) SiNPs can be produced through biomimetic synthesis in rapid (10 min), low-cost, and environmentally benign manners. The as-prepared SiNPs simultaneously feature bright fluorescence (quantum yield (QY), ∼15-20%), narrow emission spectral width (full width at half-maximum (fwhm), ∼30 nm), and nontoxicity, making them as high-quality fluorescent probes for biological imaging in vitro and in vivo.

  12. Air Oxidation of Activated Carbon to Synthesize a Biomimetic Catalyst for Hydrolysis of Cellulose.

    Science.gov (United States)

    Shrotri, Abhijit; Kobayashi, Hirokazu; Fukuoka, Atsushi

    2016-06-01

    Oxygenated carbon catalyzes the hydrolysis of cellulose present in lignocellulosic biomass by utilizing the weakly acidic functional groups on its surface. Here we report the synthesis of a biomimetic carbon catalyst by simple and economical air-oxidation of a commercially available activated carbon. Air- oxidation at 450-500 °C introduced 2000-2400 μmol g(-1) of oxygenated functional groups on the material with minor changes in the textural properties. Selectivity towards the formation of carboxylic groups on the catalyst surface increased with the increase in oxidation temperature. The degree of oxidation on carbon catalyst was found to be proportional to its activity for hydrolysis of cellulose. The hydrolysis of eucalyptus in the presence of carbon oxidized at 475 °C afforded glucose yield of 77 % and xylose yield of 67 %.

  13. Optimizing the Production of Biodiesel Using Lipase Entrapped in Biomimetic Silica

    Energy Technology Data Exchange (ETDEWEB)

    I-Ching Kuan; Chia-Chi Lee; Bing-Hong Tsai; Shiow-Ling Lee; Wei-Ting Lee; Chi-Yang Yu [Department of Bioengineering, Tatung Univ., Taipei, Taiwan (China)

    2013-04-15

    We entrapped lipase from Pseudomonas cepacia in polyallylamine-mediated biomimetic silica, and then applied entrapped lipase to the synthesis of biodiesel with soybean oil or waste cooking oil as a feedstock. The effects of reaction temperature, substrate molar ratio (methanol/oil) and n-hexane content (w/w of oil) were evaluated using response surface methodology (RSM) combined with Box-Behnken design. The optimal reaction conditions for soybean oil were 43.6 deg C, substrate molar ratio of 4.3%, and 75% n-hexane. The predicted and experimental values of biodiesel conversion were 79% and 76%, respectively. The optimal reaction conditions for waste cooking oil were 43.3 deg C, substrate molar ratio of 5%, and 38% n-hexane. The predicted and experimental values of conversion were 68% and 67%, respectively. The conversion efficiency remained the same even after 1-month storage of entrapped lipase at 4 deg C or room temperature.

  14. Tubular inverse opal scaffolds for biomimetic vessels

    Science.gov (United States)

    Zhao, Ze; Wang, Jie; Lu, Jie; Yu, Yunru; Fu, Fanfan; Wang, Huan; Liu, Yuxiao; Zhao, Yuanjin; Gu, Zhongze

    2016-07-01

    There is a clinical need for tissue-engineered blood vessels that can be used to replace or bypass damaged arteries. The success of such grafts depends strongly on their ability to mimic native arteries; however, currently available artificial vessels are restricted by their complex processing, controversial integrity, or uncontrollable cell location and orientation. Here, we present new tubular scaffolds with specific surface microstructures for structural vessel mimicry. The tubular scaffolds are fabricated by rotationally expanding three-dimensional tubular inverse opals that are replicated from colloidal crystal templates in capillaries. Because of the ordered porous structure of the inverse opals, the expanded tubular scaffolds are imparted with circumferentially oriented elliptical pattern microstructures on their surfaces. It is demonstrated that these tailored tubular scaffolds can effectively make endothelial cells to form an integrated hollow tubular structure on their inner surface and induce smooth muscle cells to form a circumferential orientation on their outer surface. These features of our tubular scaffolds make them highly promising for the construction of biomimetic blood vessels.There is a clinical need for tissue-engineered blood vessels that can be used to replace or bypass damaged arteries. The success of such grafts depends strongly on their ability to mimic native arteries; however, currently available artificial vessels are restricted by their complex processing, controversial integrity, or uncontrollable cell location and orientation. Here, we present new tubular scaffolds with specific surface microstructures for structural vessel mimicry. The tubular scaffolds are fabricated by rotationally expanding three-dimensional tubular inverse opals that are replicated from colloidal crystal templates in capillaries. Because of the ordered porous structure of the inverse opals, the expanded tubular scaffolds are imparted with circumferentially

  15. Biomimetic electrochemistry from conducting polymers. A review

    International Nuclear Information System (INIS)

    Highlights: ► Composition and properties of conducting polymers change during reactions. ► These properties are being exploited to develop biomimetic reactive and soft devices. ► The state of the art for artificial muscles sensing working conditions was reviewed. ► Smart membranes, drug delivery devices and nervous interfaces were also reviewed. - Abstract: Films of conducting polymers in the presence of electrolytes can be oxidized or reduced by the flow of anodic or cathodic currents. Ions and solvent are exchanged during a reaction for charge and osmotic pressure balance. A reactive conducting polymer contains ions and solvent. Such variation of composition during a reaction is reminiscent of the biological processes in cells. Along changes to the composition of the material during a reaction, there are also changes to other properties, including: volume (electrochemomechanical), colour (electrochromic), stored charge (electrical storage), porosity or permselectivity (electroporosity), stored chemicals, wettability and so on. Most of those properties mimic similar property changes in organs during their functioning. These properties are being exploited to develop biomimetic reactive and soft devices: artificial muscles and polymeric actuators; supercapacitors and all organic batteries; smart membranes; electron-ion transducers; nervous interfaces and artificial synapses, or drug delivery devices. In this review we focus on the state of the art for artificial muscles, smart membranes and electron-ion transducers. The reactive nature of those devices provide them with a unique advantage related to the present days technologies: any changes in the surrounding physical or chemical variable acting on the electrochemical reaction rate will be sensed by the device while working. Working under constant current (driving signal), the evolution of the device potential or the evolution of the consumed electrical energy (sensing signals) senses and quantifies the

  16. Biomimetics: forecasting the future of science, engineering, and medicine

    Directory of Open Access Journals (Sweden)

    Hwang J

    2015-09-01

    Full Text Available Jangsun Hwang,1 Yoon Jeong,1,2 Jeong Min Park,3 Kwan Hong Lee,1,2,4 Jong Wook Hong,1,2 Jonghoon Choi1,2 1Department of Bionano Technology, Graduate School, Hanyang University, Seoul, 2Department of Bionano Engineering, Hanyang University ERICA, Ansan, Korea; 3Department of Biomedical Engineering, Boston University, 4OpenView Venture Partners, Boston, MA, USA Abstract: Biomimetics is the study of nature and natural phenomena to understand the principles of underlying mechanisms, to obtain ideas from nature, and to apply concepts that may benefit science, engineering, and medicine. Examples of biomimetic studies include fluid-drag reduction swimsuits inspired by the structure of shark’s skin, velcro fasteners modeled on burrs, shape of airplanes developed from the look of birds, and stable building structures copied from the backbone of turban shells. In this article, we focus on the current research topics in biomimetics and discuss the potential of biomimetics in science, engineering, and medicine. Our report proposes to become a blueprint for accomplishments that can stem from biomimetics in the next 5 years as well as providing insight into their unseen limitations. Keywords: biomimicry, tissue engineering, biomaterials, nature, nanotechnology, nanomedicine

  17. BatSLAM: Simultaneous localization and mapping using biomimetic sonar.

    Directory of Open Access Journals (Sweden)

    Jan Steckel

    Full Text Available We propose to combine a biomimetic navigation model which solves a simultaneous localization and mapping task with a biomimetic sonar mounted on a mobile robot to address two related questions. First, can robotic sonar sensing lead to intelligent interactions with complex environments? Second, can we model sonar based spatial orientation and the construction of spatial maps by bats? To address these questions we adapt the mapping module of RatSLAM, a previously published navigation system based on computational models of the rodent hippocampus. We analyze the performance of the proposed robotic implementation operating in the real world. We conclude that the biomimetic navigation model operating on the information from the biomimetic sonar allows an autonomous agent to map unmodified (office environments efficiently and consistently. Furthermore, these results also show that successful navigation does not require the readings of the biomimetic sonar to be interpreted in terms of individual objects/landmarks in the environment. We argue that the system has applications in robotics as well as in the field of biology as a simple, first order, model for sonar based spatial orientation and map building.

  18. Effects of Biomimetic Surface Designs on Furrow Opener Performance

    Institute of Scientific and Technical Information of China (English)

    Jin Tong; Ballel. Z. Moayad; Yun-hai Ma; Ji-yu Sun; Dong-hui Chen; Hong-lei Jia; Lu-quan Ren

    2009-01-01

    The effects of biomimetic designs of tine furrow opener surface on equivalent pressure and pressure in the direction of motion on opener surface against soil were studied by finite element method (FEM) simulation and the effects of these designs on tool force and power requirements were examined experimentally. Geometrical structures of the cuticle surfaces of dung beetle (Copris ochus Motschulsky) were examined by stereoscopy. The structures of the cuticle surfaces and Ultra High Mo-lecular Weight Polyethylene (UHMWPE) material were modeled on surface of tine furrow opener as biomimetic designs. Seven furrow openers were analyzed in ANSYS program (a FEM simulation software). The biomimetic furrow opener surfaces with UHMWPE structures were found to have lower equivalent pressure and pressure in the direction of motion as compared to the conventional surface and to the biomimetic surfaces with textured steel-35 structures. It was found that the tool force and power were increased with the cutting depth and operating speed and the biomimetic furrow opener with UHMWPE tubular section ridges showed the lowest resistance and power requirement against soil.

  19. Sustainability assessment of a lightweight biomimetic ceiling structure

    International Nuclear Information System (INIS)

    An intensive and continuous debate centres on the question of whether biomimetics has a specific potential to contribute to sustainability. In the context of a case study, the objective of this paper is to contribute to this debate by presenting the first systematic approach to assess the sustainability of a complex biomimetic product. The object of inquiry is a lecture hall's ribbed slab. Based on criteria suggested by the Association of German Engineers (VDI), it has been verified that the slab has been correctly defined as biomimetic. Moreover, a systematic comparative product sustainability assessment has been carefully carried out. For purposes of comparison, estimated static calculations have been performed for conceivable current state-of-the-art lightweight ceiling structures. Alternative options are a hollow article slab and a pre-stressed flat slab. Besides a detailed benefit analysis and a discussion of social effects, their costs have also been compared. A particularly detailed life cycle assessment on the respective environmental impacts has also been performed. Results show that the biomimetic ribbed slab built in the 1960s is able to keep up with the current state-of-the-art lightweight solutions in terms of sustainability. These promising results encourage a systematic search for a broad range of sustainable biomimetic solutions. (paper)

  20. Numerical Analysis of Erosion Caused by Biomimetic Axial Fan Blade

    Directory of Open Access Journals (Sweden)

    Jun-Qiu Zhang

    2013-01-01

    Full Text Available Damage caused by erosion has been reported in several industries for a wide range of situations. In the present work, a new method is presented to improve the erosion resistance of machine components by biomimetic method. A numerical investigation of solid particle erosion in the standard and biomimetic configuration blade of axial fan is presented. The analysis consists in the application of the discrete phase model, for modeling the solid particles flow, and the Eulerian conservation equations to the continuous phase. The numerical study employs computational fluid dynamics (CFD software, based on a finite volume method. User-defined function was used to define wear equation. Gas/solid flow axial fan was simulated to calculate the erosion rate of the particles on the fan blades and comparatively analyzed the erosive wear of the smooth surface, the groove-shaped, and convex hull-shaped biomimetic surface axial flow fan blade. The results show that the groove-shaped biomimetic blade antierosion ability is better than that of the other two fan blades. Thoroughly analyze of antierosion mechanism of the biomimetic blade from many factors including the flow velocity contours and flow path lines, impact velocity, impact angle, particle trajectories, and the number of collisions.

  1. BatSLAM: Simultaneous localization and mapping using biomimetic sonar.

    Science.gov (United States)

    Steckel, Jan; Peremans, Herbert

    2013-01-01

    We propose to combine a biomimetic navigation model which solves a simultaneous localization and mapping task with a biomimetic sonar mounted on a mobile robot to address two related questions. First, can robotic sonar sensing lead to intelligent interactions with complex environments? Second, can we model sonar based spatial orientation and the construction of spatial maps by bats? To address these questions we adapt the mapping module of RatSLAM, a previously published navigation system based on computational models of the rodent hippocampus. We analyze the performance of the proposed robotic implementation operating in the real world. We conclude that the biomimetic navigation model operating on the information from the biomimetic sonar allows an autonomous agent to map unmodified (office) environments efficiently and consistently. Furthermore, these results also show that successful navigation does not require the readings of the biomimetic sonar to be interpreted in terms of individual objects/landmarks in the environment. We argue that the system has applications in robotics as well as in the field of biology as a simple, first order, model for sonar based spatial orientation and map building.

  2. Conventional vs Biomimetic Approaches to the Exploration of Mars

    Science.gov (United States)

    Ellery, A.

    It is not usual to refer to convention in planetary exploration missions by virtue of the innovation required for such projects. The term conventional refers to the methodologies, tools and approaches typically adopted in engineering that are applied to such missions. Presented is a "conventional" Mars rover mission in which the author was involved - ExoMars - into which is interspersed references to examples where biomimetic approaches may yield superior capabilities. Biomimetics is a relatively recently active area of research which seeks to examine how biological systems solve the problem of survival in the natural environment. Biological organisms are autonomous entities that must survive in a hostile world adapting both adaptivity and robustness. It is not then surprising that biomimetics is particularly useful when applied to robotic elements of a Mars exploration mission. I present a number of areas in which biomimetics may yield new solutions to the problem of Mars exploration - optic flow navigation, potential field navigation, genetically-evolved neuro-controllers, legged locomotion, electric motors implementing muscular behaviour, and a biomimetic drill based on the wood wasp ovipositor. Each of these techniques offers an alternative approach to conventional ones. However, the perceptive hurdles are likely to dwarf the technical hurdles in implementing many of these methods in the near future.

  3. A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related natural and nonnatural compounds.

    Science.gov (United States)

    Zhang, Wei; Bah, Juho; Wohlfarth, Andreas; Franzén, Johan

    2011-12-01

    Here we present a general and common catalytic asymmetric strategy for the total and formal synthesis of a broad number of optically active natural products from the corynantheine and ipecac alkaloid families, for example, indolo[2,3-a]- and benzo[a]quinolizidines. Construction of the core alkaloid skeletons with the correct absolute and relative stereochemistry relies on an enantioselective and diastereodivergent one-pot cascade sequence followed by an additional diastereodivergent reaction step. This allows for enantio- and diastereoselective synthesis of three out of four possible epimers of the quinolizidine alkaloids that begin from common and easily accessible starting materials by using a common synthetic route. Focus has been made on excluding protecting groups and limiting isolation and purification of synthetic intermediates. This methodology is applied in the total synthesis of the natural products (-)-dihydrocorynantheol, (-)-hirsutinol, (-)-corynantheol, (-)-protometinol, (-)-dihydrocorynantheal, (-)-corynantheal, (-)-protoemetine, (-)-(15S)-hydroxydihydrocorynantheol, and an array of their nonnatural epimers. The potential of this strategy is also demonstrated in the synthesis of biologically interesting natural product analogues not accessible through synthetic elaboration of alkaloid precursors available from nature, for example, thieno[3,2-a]quinolizidine derivatives. We also report the formal synthesis of (+)-dihydrocorynantheine, (-)-emetine, (-)-cephaeline, (-)-tubulosine, and (-)-deoxytubulosine.

  4. Biomimetic Coacervate Environments for Protein Analysis

    Science.gov (United States)

    Perry, Sarah; McCall, Patrick; Srivastava, Samavayan; Kovar, David; Gardel, Margaret; Tirrell, Matthew

    2015-03-01

    Living cells have evolved sophisticated intracellular organization strategies that are challenging to reproduce synthetically. Biomolecular function depends on both the structure of the molecule itself and the properties of the surrounding medium. The ability to simulate the in vivo environment and isolate biological networks for study in an artificial milieu without sacrificing the crowding, structure, and compartmentalization of a cellular environment, represent engineering challenges with tremendous potential to impact both biological studies and biomedical applications. Emerging experience has shown that polypeptide-based complex coacervation (electrostatically-driven liquid-liquid phase separation) produces a biomimetic microenvironment capable of tuning protein biochemical activity. We have investigated the effect of polypeptide-based coacervates on the dynamic self-assembly of cytoskeletal actin filaments. Coacervate materials are able to directly affect the nucleation and assembly dynamics. We observe effects that can be attributed to the length and chemical specificity of the encapsulating polypeptides, as well as the overall crowded nature of a polymer-rich coacervate phase. Coacervate-based systems are particularly attractive for use in biochemical assays because the compartmentalization afforded by liquid-liquid phase separation does not necessarily inhibit the transport of molecules across the compartmental barrier.

  5. Mineralization of Zein Films by Biomimetic Process

    Institute of Scientific and Technical Information of China (English)

    JIN Xiaoning; ZHANG Yanxiang; MA Ying; ZENG Sheng; WANG Shaozhen; MA Yalu

    2015-01-01

    The transparent or opaque zein film was prepared by a phase separation method with a zein ethanol aqueous solution. The circular zein film was self-assembled on the air-water interface. According to the images by scanning elec-tron microscopy, the upper surface of film is flat and smooth and the downward surface presents a complex reticulation structure of corn protein fiber. Zein film as a biomimetic mineralization template is used to synthesize calcium phosphate crystals by a bioinspired mineralization process. Randomly oriented apatite crystals appear on the both surfaces of zein film after immersion in 10´simulated body fluid, and the phase composition and morphology of the deposited calcium apatite are also distinguished from deposited location and immersion time. The phase transformation process from dical-cium phosphate dihydrate into hydroxyapatite (HAp) phase was investigated by X-ray powder diffraction, transmission electron microscopy and Fourier transform infrared spectroscopy, respectively. Based on the results by energy dispersive X-ray spectroscopy, the Ca/P ratio of the deposited apatite increases with the transformation from DCPD to HAp. The HAp/Zein films possess the excellent biodegradable structural features, and the coating of HAp crystallites has some potential applications for bone repair and regeneration.

  6. Biomimetic optical sensor for aerospace applications

    Science.gov (United States)

    Frost, Susan A.; Gorospe, George E.; Wright, Cameron H. G.; Barrett, Steven F.

    2015-05-01

    We report on a fiber optic sensor based on the physiological aspects of the eye and vision-related neural layers of the common housefly (Musca domestica) that has been developed and built for aerospace applications. The intent of the research is to reproduce select features from the fly's vision system that are desirable in image processing, including high functionality in low-light and low-contrast environments, sensitivity to motion, compact size, lightweight, and low power and computation requirements. The fly uses a combination of overlapping photoreceptor responses that are well approximated by Gaussian distributions and neural superposition to detect image features, such as object motion, to a much higher degree than just the photoreceptor density would imply. The Gaussian overlap in the biomimetic sensor comes from the front-end optical design, and the neural superposition is accomplished by subsequently combining the signals using analog electronics. The fly eye sensor is being developed to perform real-time tracking of a target on a flexible aircraft wing experiencing bending and torsion loads during flight. We report on results of laboratory experiments using the fly eye sensor to sense a target moving across its field of view.

  7. Biomimetic Pattern Recognition Theory and Its Applications

    Institute of Scientific and Technical Information of China (English)

    WANGShoujue; ZHAOXingtao

    2004-01-01

    Biomimetic pattern recogntion (BPR),which is based on “cognition” instead of “classification”,is much closer to the function of human being. The basis of BPR is the Principle of homology-continuity (PHC),which means the difference between two samples of the same class must be gradually changed. The aim of BPR is to find an optimal covering in the feature space, which emphasizes the “similarity” among homologous group members, rather than “division” in traditional pattern recognition. Some applications of BPR are surveyed, in which the results of BPR are much better than the results of Support Vector Machine. A novel neuron model, Hyper sausage neuron (HSN), is shown as a kind of covering units in BPR. The mathematical description of HSN is given and the 2-dimensional discriminant boundary of HSN is shown. In two special cases, in which samples are distributed in a line segment and a circle, both the HSN networks and RBF networks are used for covering. The results show that HSN networks act better than RBF networks in generalization, especially for small sample set, which are consonant with the results of the applications of BPR. And a brief explanation of the HSN networks' advantages in covering general distributed samples is also given.

  8. Bactericidal activity of biomimetic diamond nanocone surfaces.

    Science.gov (United States)

    Fisher, Leanne E; Yang, Yang; Yuen, Muk-Fung; Zhang, Wenjun; Nobbs, Angela H; Su, Bo

    2016-03-01

    The formation of biofilms on implant surfaces and the subsequent development of medical device-associated infections are difficult to resolve and can cause considerable morbidity to the patient. Over the past decade, there has been growing recognition that physical cues, such as surface topography, can regulate biological responses and possess bactericidal activity. In this study, diamond nanocone-patterned surfaces, representing biomimetic analogs of the naturally bactericidal cicada fly wing, were fabricated using microwave plasma chemical vapor deposition, followed by bias-assisted reactive ion etching. Two structurally distinct nanocone surfaces were produced, characterized, and the bactericidal ability examined. The sharp diamond nanocone features were found to have bactericidal capabilities with the surface possessing the more varying cone dimension, nonuniform array, and decreased density, showing enhanced bactericidal ability over the more uniform, highly dense nanocone surface. Future research will focus on using the fabrication process to tailor surface nanotopographies on clinically relevant materials that promote both effective killing of a broader range of microorganisms and the desired mammalian cell response. This study serves to introduce a technology that may launch a new and innovative direction in the design of biomaterials with capacity to reduce the risk of medical device-associated infections. PMID:26992656

  9. Development of Underwater Microrobot with Biomimetic Locomotion

    Directory of Open Access Journals (Sweden)

    W. Zhang

    2006-01-01

    Full Text Available Microrobots have powerful applications in biomedical and naval fields. They should have a compact structure, be easy to manufacture, have efficient locomotion, be driven by low voltage and have a simple control system. To meet these purposes, inspired by the leg of stick insects, we designed a novel type of microrobot with biomimetic locomotion with 1-DOF (degree of freedom legs. The locomotion includes two ionic conducting polymer film (ICPF actuators to realize the 2-DOF motion. We developed several microrobots with this locomotion. Firstly, we review a microrobot, named Walker-1, with 1-DOF motion. And then a new microrobot, named Walker-2, utilizing six ICPF actuators, with 3-DOF motion is introduced. It is 47 mm in diameter and 8 mm in height (in static state. It has 0.61 g of dried weight. We compared the two microrobot prototypes, and the result shows that Walker-2 has some advantages, such as more flexible moving motion, good balance, less water resistance, more load-carrying ability and so on. We also compared it with some insect-inspired microrobots and some microrobots with 1-DOF legs, and the result shows that a microrobot with this novel type of locomotion has some advantages. Its structure has fewer actuators and joints, a simpler control system and is compact. The ICPF actuator decides that it can be driven by low voltage (less than 5 V and move in water. A microrobot with this locomotion has powerful applications in biomedical and naval fields.

  10. Software architecture of biomimetic underwater vehicle

    Science.gov (United States)

    Praczyk, Tomasz; Szymak, Piotr

    2016-05-01

    Autonomous underwater vehicles are vehicles that are entirely or partly independent of human decisions. In order to obtain operational independence, the vehicles have to be equipped with a specialized software. The main task of the software is to move the vehicle along a trajectory with collision avoidance. Moreover, the software has also to manage different devices installed on the vehicle board, e.g. to start and stop cameras, sonars etc. In addition to the software embedded on the vehicle board, the software responsible for managing the vehicle by the operator is also necessary. Its task is to define mission of the vehicle, to start, to stop the mission, to send emergency commands, to monitor vehicle parameters, and to control the vehicle in remotely operated mode. An important objective of the software is also to support development and tests of other software components. To this end, a simulation environment is necessary, i.e. simulation model of the vehicle and all its key devices, the model of the sea environment, and the software to visualize behavior of the vehicle. The paper presents architecture of the software designed for biomimetic autonomous underwater vehicle (BAUV) that is being constructed within the framework of the scientific project financed by Polish National Center of Research and Development.

  11. A multi-electrode biomimetic electrolocation sensor

    Science.gov (United States)

    Mayekar, K.; Damalla, D.; Gottwald, M.; Bousack, H.; von der Emde, G.

    2012-04-01

    We present the concept of an active multi-electrode catheter inspired by the electroreceptive system of the weakly electric fish, Gnathonemus petersii. The skin of this fish exhibits numerous electroreceptor organs which are capable of sensing a self induced electrical field. Our sensor is composed of a sending electrode and sixteen receiving electrodes. The electrical field produced by the sending electrode was measured by the receiving electrodes and objects were detected by the perturbation of the electrical field they induce. The intended application of such a sensor is in coronary diagnostics, in particular in distinguishing various types of plaques, which are major causes of heart attack. For calibration of the sensor system, finite element modeling (FEM) was performed. To validate the model, experimental measurements were carried out with two different systems. The physical system was glass tubing with metal and plastic wall insertions as targets. For the control of the experiment and for data acquisition, the software LabView designed for 17 electrodes was used. Different parameters of the electric images were analyzed for the prediction of the electrical properties and size of the inserted targets in the tube. Comparisons of the voltage modulations predicted from the FEM model and the experiments showed a good correspondence. It can be concluded that this novel biomimetic method can be further developed for detailed investigations of atherosclerotic lesions. Finally, we discuss various design strategies to optimize the output of the sensor using different simulated models to enhance target recognition.

  12. Biomimetic visual detection based on insect neurobiology

    Science.gov (United States)

    O'Carroll, David C.

    2001-11-01

    With a visual system that accounts for as much as 30% of the lifted mass, flying insects such as dragonflies and hoverflies invest more in vision than any other animal. Impressive visual performance is subserved by a surprisingly simple visual system. In a typical insect eye, between 2,000 and 30,000 pixels in the image are analyzed by fewer than 200,000 neurons in underlying neural circuits. The combination of sophisticated visual processing with an approachable level of complexity has made the insect visual system a leading model for biomimetic approaches to computer vision. Much neurobiological research has focused on neural circuits used for detection of moving patterns (e.g. optical flow during flight) and moving targets (e.g. prey). Research from several labs has led to great advances in our understanding of the neural mechanisms involved, and has spawned neuromorphic hardware based on key processes identified in neurobiological experiments. Despite its attractions, the highly non-linear nature of several key stages in insect visual processing presents a challenge to understanding. I will describe examples of adaptive elements of neural circuits in the fly visual system which analyze the direction and velocity of wide-field optical flow patterns and the result of experiments that suggest that these non-linearities may contribute to robust responses to natural image motion.

  13. Biomimetic Nanotechnology: A Powerful Means to address Global Challenges

    CERN Document Server

    Gebeshuber, Ille C

    2010-01-01

    Biomimetic nanotechnology is a prominent research area at the meeting place of life sciences with engineering and physics: it is a continuously growing field that deals with knowledge transfer from biology to nanotechnology. Biomimetic nanotechnology is a field that has the potential to substantially support successful mastering of major global challenges. The Millennium Project was commissioned by the United Nations Secretary-General in 2002 to develop a concrete action plan for the world to reverse the grinding poverty, hunger and disease affecting billions of people. It states 15 Global Challenges: sustainable development, water, population and resources, democratization, long-term perspectives, information technology, the rich-poor gap, health, capacity to decide, peace and conflict, status of women, transnational crime, energy, science and technology and global ethics. The possible contributions to master these challenges with the help of biomimetic nanotechnology will be discussed in detail.

  14. Tribological and electrochemical studies on biomimetic synovial fluids

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    In this study, tribological and electrochemical performances of the new biomimetic synovial fluids were studied according to different composition concentrations, including hyaluronic acid, albumin and alendronic acid sodium. By using Taguchi method, the composition contents of the biomimetic synovial fluids were designed. Items such as friction coefficient, mean scar diameter and viscosity were investigated via a four-ball tribo-tester, viscosity meter and optical microscope. Polarization studies were carried out to analyze the electrochemical behaviour of the fluids. Results showed that hyaluronic acid dominates the viscosity of the fluids. High albumin concentration will reduce friction, while increasing wear rate due to the electro-chemical effect. Alendronic acid sodium is found to reduce the biocorrosion of CoCrMo as well as provide better lubricating. In conclusion, biomimetic synovial fluids partially recover the functions of natural synovial fluids and provide good lubricating property.

  15. PEM Fuel Cells Redesign Using Biomimetic and TRIZ Design Methodologies

    Science.gov (United States)

    Fung, Keith Kin Kei

    Two formal design methodologies, biomimetic design and the Theory of Inventive Problem Solving, TRIZ, were applied to the redesign of a Proton Exchange Membrane (PEM) fuel cell. Proof of concept prototyping was performed on two of the concepts for water management. The liquid water collection with strategically placed wicks concept demonstrated the potential benefits for a fuel cell. Conversely, the periodic flow direction reversal concepts might cause a potential reduction water removal from a fuel cell. The causes of this water removal reduction remain unclear. In additional, three of the concepts generated with biomimetic design were further studied and demonstrated to stimulate more creative ideas in the thermal and water management of fuel cells. The biomimetic design and the TRIZ methodologies were successfully applied to fuel cells and provided different perspectives to the redesign of fuel cells. The methodologies should continue to be used to improve fuel cells.

  16. Desalination by biomimetic aquaporin membranes: Review of status and prospects

    DEFF Research Database (Denmark)

    Tang, C.Y.; Zhao, Y.; Wang, R.;

    2013-01-01

    Based on their unique combination of offering high water permeability and high solute rejection aquaporin proteins have attracted considerable interest over the last years as functional building blocks of biomimetic membranes for water desalination and reuse. The purpose of this review...... is to provide an overview of the properties of aquaporins, their preparation and characterization. We discuss the challenges in exploiting the remarkable properties of aquaporin proteins for membrane separation processes and we present various attempts to construct aquaporin in membranes for desalination......; including an overview of our own recent developments in aquaporin-based membranes. Finally we outline future prospects of aquaporin based biomimetic membrane for desalination and water reuse....

  17. Biomimetic actuators using electroactive polymers (EAP) as artificial muscles

    Science.gov (United States)

    Bar-Cohen, Yoseph

    2006-01-01

    Evolution has resolved many of nature's challenges leading to lasting solutions with maximal performance and effective use of resources. Nature's inventions have always inspired human achievements leading to effective materials, structures, tools, mechanisms, processes, algorithms, methods, systems and many other benefits. The field of mimicking nature is known as Biomimetics and one of its topics includes electroactive polymers that gain the moniker artificial muscles. Integrating EAP with embedded sensors, self-repair and many other capabilities that are used in composite materials can add greatly to the capability of smart biomimetic systems. Such development would enable fascinating possibilities potentially turning science fiction ideas into engineering reality.

  18. Reduced stress shielding with limited micromotions using a carbon fibre composite biomimetic hip stem: a finite element model.

    Science.gov (United States)

    Caouette, C; Yahia, L H; Bureau, M N

    2011-09-01

    Total hip arthroplasty (THA) enjoys excellent rates of success in older patients, but younger patients are still at risk of aseptic loosening and bone resorption from stress shielding. One solution to the stress shielding problem is to use a hip stem with mechanical properties matching those of cortical bone. The objective of the present study was to investigate numerically the biomechanical performance of such a biomimetic hip stem based on a hydroxyapatite (HA)-coated carbon fibre composite. A finite element model (FEM) of the biomimetic stem was constructed. Contact elements were studied to model the bone-implant interface in a non-osseointegrated and osseointegrated state in the best way. Three static load cases representing slow walking, stair climbing, and gait in a healthy individual were considered. Stress shielding and bone-implant interface micromotions were evaluated and compared with the results of a similar FEM based on titanium alloy (Ti-6Al-4V). The composite stems allowed for reduced stress shielding when compared with a traditional Ti-6Al-4V stem. Micromotions were slightly higher with the composite stem, but remained below 40 microm on most of the HA-coated surface. It is concluded that a biomimetic composite stem might offer a better compromise between stress shielding and micromotions than the Ti-6Al-4V stem with the same external geometry.

  19. Engineering nanomaterials with a combined electrochemical and molecular biomimetic approach

    Science.gov (United States)

    Dai, Haixia

    Biocomposite materials, such as bones, teeth, and shells, are created using mild aqueous solution-based processes near room temperature. Proteins add flexibility to these processes by facilitating the nucleation, growth, and ordering of specific inorganic materials into hierarchical structures. We aim to develop a biomimetic strategy for engineering technologically relevant inorganic materials with controlled compositions and structures, as Nature does, using proteins to orchestrate material formation and assembly. This approach involves three basic steps: (i) preparation of inorganic substrates compatible with combinatorial polypeptide screening; (ii) identification of inorganic-binding polypeptides and their engineering into inorganic-binding proteins; and (iii) protein-mediated inorganic nucleation and organization. Cuprous oxide (Cu2O), a p-type semiconductor, has been used to demonstrate all three steps. Zinc oxide (ZnO), an n-type semiconductor, has been used to show the generality of selected steps. Step (i), preparation of high quality inorganic substrates to select inorganic-binding polypeptides, was accomplished using electrochemical microfabrication to grow and pattern Cu2O and ZnO. Raman spectroscopy and x-ray photoelectron spectroscopy were used to verify phase purity and compositional stability of these surfaces during polypeptide screening. Step (ii), accomplished in collaboration with personnel in Prof Baneyx' lab at the University of Washington, involved incubating the inorganic substrates with the FliTrx(TM) random peptide library to identify cysteine-constrained dodecapeptides that bind the targeted inorganic. Insertion of a Cu2O-binding dodecapeptide into the DNA-binding protein TraI endowed the engineered TraI with strong affinity for Cu2O (Kd ≈ 10 -8 M). Finally, step (iii) involved nonequilibrium synthesis and organization of Cu2O nanoparticles, taking advantage of the inorganic and DNA recognition properties of the engineered TraI. The

  20. Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities.

    Science.gov (United States)

    Barbie, Philipp; Kazmaier, Uli

    2016-07-01

    Cyclomarins are cyclic heptapeptides containing four unusual amino acids. New synthetic protocols toward their synthesis have been developed, leading to the synthesis and biological evaluation of three natural occurring cyclomarins. Interestingly, cyclomarins address two completely different targets: Clp C1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Ase of Plasmodium falciparum. Therefore, cyclomarins are interesting lead structures for the development of drugs against tuberculosis and malaria. PMID:27241518

  1. Effects of Oxygen Transfer Limitation and Kinetic Control on Biomimetic Catalytic Oxidation of Toluene

    Institute of Scientific and Technical Information of China (English)

    罗伟平; 刘大为; 孙俊; 邓伟; 盛文兵; 刘强; 郭灿城

    2014-01-01

    Under oxygen transfer limitation and kinetic control, liquid-phase catalytic oxidation of toluene over metalloporphyrin was studied. An improved technique of measuring dissolved oxygen levels for gas-liquid reaction at the elevated temperature and pressure was used to take the sequential data in the oxidation of toluene catalyzed by metalloporphyrin. By this technique the corresponding control step of toluene oxidation could be obtained by varying reaction conditions. When the partial pressure of oxygen in the feed is lower than or equal to 0.070 MPa at 463 K, the oxidation of toluene would be controlled by oxygen transfer, otherwise the reaction would be controlled by kinetics. The effects of both oxygen transfer and kinetic control on the toluene conversion and the selectivity of benzaldehyde and benzyl alcohol in biomimetic catalytic oxidation of toluene were systematically investigated. Three conclusions have been made from the experimental results. Firstly, under the oxygen transfer limitation the toluene conversion is lower than that under kinetic control at the same oxidation conditions. Secondly, under the oxygen transfer limitation the total selectivity of benzaldehyde and benzyl alcohol is lower than that under kinetic control with the same conversion of toluene. Finally, under the kinetics control the oxidation rate of toluene is zero-order with respect to oxygen. The experimental results are identical with the biomimetic catalytic mechanism of toluene oxidation over metalloporphyrins.

  2. Chiral discrimination in biomimetic systems: Phenylalanine

    Indian Academy of Sciences (India)

    K Thirumoorthy; K Soni; T Arun; N Nandi

    2007-09-01

    Chiral discrimination and recognition is important in peptide biosynthesis, amino acid synthesis and drug designing. Detailed structural information is available about the peptide synthesis in ribosome. However, no detailed study is available about the discrimination in peptide synthesis. We study the conformational energy variation of neutral methoxy phenyl alanine molecule as a function of its different dihedral angle to locate the minimum energy conformation using quantum chemical theory. We compared the intermolecular energy surfaces of phenyl alanine molecule in its neutral and zwitterionic state using quantum chemical theory as a function of distance and mutual orientation. The energy surfaces are studied with rigid geometry by varying the distance and orientation. The potential energy surfaces of - and - pairs are found to be dissimilar and reflect the underlying chirality of the homochiral pair and racemic nature of the heterochiral pair. The intermolecular energy surface of homochiral pair is more favourable than the corresponding energy surface of heterochiral pair.

  3. Bio-Mimetic Sensors Based on Molecularly Imprinted Membranes

    Directory of Open Access Journals (Sweden)

    Catia Algieri

    2014-07-01

    Full Text Available An important challenge for scientific research is the production of artificial systems able to mimic the recognition mechanisms occurring at the molecular level in living systems. A valid contribution in this direction resulted from the development of molecular imprinting. By means of this technology, selective molecular recognition sites are introduced in a polymer, thus conferring it bio-mimetic properties. The potential applications of these systems include affinity separations, medical diagnostics, drug delivery, catalysis, etc. Recently, bio-sensing systems using molecularly imprinted membranes, a special form of imprinted polymers, have received the attention of scientists in various fields. In these systems imprinted membranes are used as bio-mimetic recognition elements which are integrated with a transducer component. The direct and rapid determination of an interaction between the recognition element and the target analyte (template was an encouraging factor for the development of such systems as alternatives to traditional bio-assay methods. Due to their high stability, sensitivity and specificity, bio-mimetic sensors-based membranes are used for environmental, food, and clinical uses. This review deals with the development of molecularly imprinted polymers and their different preparation methods. Referring to the last decades, the application of these membranes as bio-mimetic sensor devices will be also reported.

  4. An efficient biomimetic coating methodology for a prosthetic alloy

    Energy Technology Data Exchange (ETDEWEB)

    Adawy, Alaa, E-mail: a.adawy@science.ru.nl [Physics Department, Faculty of Science, Ain Shams University, Abbassia, Cairo (Egypt); Abdel-Fattah, Wafa I. [Biomaterials Department, National Research Centre, Giza (Egypt)

    2013-04-01

    The combination of the load-bearing metallic implants with the bioactive materials in the design of synthetic implants is an important aspect in the biomaterials research. Biomimetic coating of bioinert alloys with calcium phosphate phases provides a good alternative to the prerequisite for the continual replacement of implants because of the failure of bone-implant integration. We attempted to accelerate the biomimetic coating process of stainless steel alloy (316L) with biomimetic apatite. In addition, we investigated the incorporation of functioning minerals such as strontianite and smithsonite into the deposited layer. In order to develop a highly mature apatite coating, our method requires soaking of the pre-treated alloy in highly concentrated synthetic body fluid for only few hours. Surface characterizations were performed by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and Diffuse Reflectance Infrared Fourier Transform Spectroscopy (DRIFTS). Also, the deposited apatitic layers were analysed by powder diffraction X-ray analysis (XRD). 316L surface showed the growth of highly crystalline, low carbonated hydroxyapatite, after only 6 h of the whole soaking process. Highlights: ► The manuscript describes a fast and efficient biomimetic coating methodology. ► This methodology can be used for metallic implants. ► 316L was coated with crystalline hydroxyapatite. ► Addition of strontium and zinc lead to the deposition of brushite. ► Coating of all synthetic solutions is highly crystalline.

  5. Design and Implementation of a Modular Biomimetic Infochemical Communication System

    NARCIS (Netherlands)

    Rácz, Z.; Cole, M.; Gardner, J.W.; Chowdhury, M.F.; Bula, W.P.; Gardeniers, J.G.E.; Karout, S.; Capurro, A.; Pearce, T.C.

    2013-01-01

    We describe here the design and implementation of a novel biomimetic infochemical communication system that employs airborne molecules alone to communicate over space and time. The system involves the design and fabrication of a microsystem capable of producing and releasing a precise mix of biosynt

  6. A biomimetic tactile sensing system based on polyvinylidene fluoride film

    Science.gov (United States)

    Xin, Yi; Tian, Hongying; Guo, Chao; Li, Xiang; Sun, Hongshuai; Wang, Peiyuan; Qian, Chenghui; Wang, Shuhong; Wang, Cheng

    2016-02-01

    Polyvinylidene fluoride (PVDF) film has been widely investigated as a sensing material due to its outstanding properties such as biocompatibility, high thermal stability, good chemical resistance, high piezo-, pyro- and ferro-electric properties. This paper reports on the design, test, and analysis of a biomimetic tactile sensor based on PVDF film. This sensor consists of a PVDF film with aluminum electrodes, a pair of insulating layers, and a "handprint" friction layer with a copper foil. It is designed for easy fabrication and high reliability in outputting signals. In bionics, the fingerprint of the glabrous skin plays an important role during object handling. Therefore, in order to enhance friction and to provide better manipulation, the ridges of the fingertips were introduced into the design of the proposed tactile sensor. And, a basic experimental study on the selection of the high sensitivity fingerprint type for the biomimetic sensor was performed. In addition, we proposed a texture distinguish experiment to verify the sensor sensitivity. The experiment's results show that the novel biomimetic sensor is effective in discriminating object surface characteristics. Furthermore, an efficient visual application program (LabVIEW) and a quantitative evaluation method were proposed for the verification of the biomimetic sensor. The proposed tactile sensor shows great potential for contact force and slip measurements.

  7. Case Study in Biomimetic Design: Handling and Assembly of Microparts

    DEFF Research Database (Denmark)

    Shu, Li; Hansen, Hans Nørgaard; Gegeckaite, Asta;

    2006-01-01

    This paper describes the application of the biomimetic design process to the development of automated gripping devices for microparts. Handling and assembly of micromechanical parts is complicated by size effects that occur when part dimensions are scaled down. A common complication involves...

  8. Diffraction from relief gratings on a biomimetic elastomer cast

    International Nuclear Information System (INIS)

    Biomimetic optical elements combine the optimized designs of nature with the versatility of materials engineering. We employ a beetle carapace as the template for fabricating relief gratings on an elastomer substrate. Biological surface features are successfully replicated by a direct casting procedure. Far-field diffraction effects are discussed in terms of the Fraunhofer approximation in Fourier space.

  9. 3D Modelling of Biological Systems for Biomimetics

    Institute of Scientific and Technical Information of China (English)

    Shujun Zhang; Kevin Hapeshi; Ashok K. Bhattacharya

    2004-01-01

    With the advanced development of computer-based enabling technologies, many engineering, medical, biology,chemistry, physics and food science etc have developed to the unprecedented levels, which lead to many research and development interests in various multi-discipline areas. Among them, biomimetics is one of the most promising and attractive branches of study. Biomimetics is a branch of study that uses biological systems as a model to develop synthetic systems.To learn from nature, one of the fundamental issues is to understand the natural systems such animals, insects, plants and human beings etc. The geometrical characterization and representation of natural systems is an important fundamental work for biomimetics research. 3D modeling plays a key role in the geometrical characterization and representation, especially in computer graphical visualization. This paper firstly presents the typical procedure of 3D modelling methods and then reviews the previous work of 3D geometrical modelling techniques and systems developed for industrial, medical and animation applications. Especially the paper discusses the problems associated with the existing techniques and systems when they are applied to 3D modelling of biological systems. Based upon the discussions, the paper proposes some areas of research interests in 3D modelling of biological systems and for Biomimetics.

  10. Preparation, anti-biofouling and drag-reduction properties of a biomimetic shark skin surface

    OpenAIRE

    Xia Pu; Guangji Li; Hanlu Huang

    2016-01-01

    ABSTRACT Shark skin surfaces show non-smoothness characteristics due to the presence of a riblet structure. In this study, biomimetic shark skin was prepared by using the polydimethylsiloxane (PDMS)-embedded elastomeric stamping (PEES) method. Scanning electron microscopy (SEM) was used to examine the surface microstructure and fine structure of shark skin and biomimetic shark skin. To analyse the hydrophobic mechanism of the shark skin surface microstructure, the effect of biomimetic shark s...

  11. Waste utilization for the controlled synthesis of nanosized hydroxyapatite

    International Nuclear Information System (INIS)

    This work uses biomolecules in waste and medicinally important materials for the synthesis of hydroxyapatite nanoparticles. Orange and potato peel, eggshell, papaya leaf and calendula flower extracts have varied biomolecules, which exert a significant, control on the in situ synthesis of nanosized hydroxyapatite particles. The biomimetic synthesis of inorganic particles using known matrices is already well established, however, there are only a few reports using compound extracts. The synthesized nanocomposite has been characterized using X-ray diffraction, Fourier transform infrared spectroscopy and scanning electron microscopy studies. Role of varied biomolecules in controlled inorganic synthesis may have tremendous technological impact.

  12. Waste utilization for the controlled synthesis of nanosized hydroxyapatite

    Energy Technology Data Exchange (ETDEWEB)

    Nayar, Suprabha, E-mail: Suprabha.nayar@gmail.com [National Metallurgical Laboratory, Jamshedpur (India); Guha, Avijit [National Metallurgical Laboratory, Jamshedpur (India)

    2009-05-05

    This work uses biomolecules in waste and medicinally important materials for the synthesis of hydroxyapatite nanoparticles. Orange and potato peel, eggshell, papaya leaf and calendula flower extracts have varied biomolecules, which exert a significant, control on the in situ synthesis of nanosized hydroxyapatite particles. The biomimetic synthesis of inorganic particles using known matrices is already well established, however, there are only a few reports using compound extracts. The synthesized nanocomposite has been characterized using X-ray diffraction, Fourier transform infrared spectroscopy and scanning electron microscopy studies. Role of varied biomolecules in controlled inorganic synthesis may have tremendous technological impact.

  13. Biomimetic tissue-engineered systems for advancing cancer research: NCI Strategic Workshop report.

    Science.gov (United States)

    Schuessler, Teresa K; Chan, Xin Yi; Chen, Huanhuan Joyce; Ji, Kyungmin; Park, Kyung Min; Roshan-Ghias, Alireza; Sethi, Pallavi; Thakur, Archana; Tian, Xi; Villasante, Aranzazu; Zervantonakis, Ioannis K; Moore, Nicole M; Nagahara, Larry A; Kuhn, Nastaran Z

    2014-10-01

    Advanced technologies and biomaterials developed for tissue engineering and regenerative medicine present tractable biomimetic systems with potential applications for cancer research. Recently, the National Cancer Institute convened a Strategic Workshop to explore the use of tissue biomanufacturing for development of dynamic, physiologically relevant in vitro and ex vivo biomimetic systems to study cancer biology and drug efficacy. The workshop provided a forum to identify current progress, research gaps, and necessary steps to advance the field. Opportunities discussed included development of tumor biomimetic systems with an emphasis on reproducibility and validation of new biomimetic tumor models, as described in this report.

  14. Biomimetic staggered composites with highly enhanced energy dissipation: Modeling, 3D printing, and testing

    Science.gov (United States)

    Zhang, Pu; Heyne, Mary A.; To, Albert C.

    2015-10-01

    We investigate the damping enhancement in a class of biomimetic staggered composites via a combination of design, modeling, and experiment. In total, three kinds of staggered composites are designed by mimicking the structure of bone and nacre. These composite designs are realized by 3D printing a rigid plastic and a viscous elastomer simultaneously. Greatly-enhanced energy dissipation in the designed composites is observed from both the experimental results and theoretical prediction. The designed polymer composites have loss modulus up to ~500 MPa, higher than most of the existing polymers. In addition, their specific loss modulus (up to 0.43 km2/s2) is among the highest of damping materials. The damping enhancement is attributed to the large shear deformation of the viscous soft matrix and the large strengthening effect from the rigid inclusion phase.

  15. Total protein

    Science.gov (United States)

    ... page: //medlineplus.gov/ency/article/003483.htm Total protein To use the sharing features on this page, please enable JavaScript. The total protein test measures the total amount of two classes ...

  16. Biomimetic oligosaccharide and peptide surfactant polymers designed for cardiovascular biomaterials

    Science.gov (United States)

    Ruegsegger, Mark Andrew

    A common problem associated with cardiovascular devices is surface induced thrombosis initiated by the rapid, non-specific adsorption of plasma proteins onto the biomaterial surface. Control of the initial protein adsorption is crucial to achieve the desired longevity of the implanted biomaterial. The cell membrane glycocalyx acts as a non-thrombogenic interface through passive (dense oligosaccharide structures) and active (ligand/receptor interactions) mechanisms. This thesis is designed to investigate biomimicry of the cell glycocalyx to minimize non-specific protein adsorption and promote specific ligand/receptor interactions. Biomimetic macromolecules were designed through the molecular-scale engineering of polymer surfactants, utilizing a poly(vinyl amine) (PVAm) backbone to which hydrophilic (dextran, maltose, peptide) and hydrophobic alkyl (hexanoyl or hexanal) chains are simultaneously attached. The structure was controlled through the molar feed ratio of hydrophobic-to-hydrophilic groups, which also provided control of the solution and surface-active properties. To mimic passive properties, a series of oligomaltose surfactants were synthesized with increasing saccharide length (n = 2, 7, 15 where n is number of glucose units) to investigate the effect of coating height on protein adsorption. The surfactants were characterized by infra red (IR) and nuclear magnetic resonance (NMR) spectroscopies for structural properties and atomic force microscopy (AFM) and contact angle goniometry for surface activity. Protein adsorption under dynamic flow (5 dyn/cm2) was reduced by 85%--95% over the bare hydrophobic substrate; platelet adhesion dropped by ˜80% compared to glass. Peptide ligands were incorporated into the oligosaccharide surfactant to promote functional activity of the passive coating. The surfactants were synthesized to contain 0%, 25%, 50%, 75%, and 100% peptide ligand density and were stable on hydrophobic surfaces. The peptide surface density was

  17. Total Synthesis and Biological Evaluation of a Series of Macrocyclic Hybrids and Analogues of the Antimitotic Natural Products Dictyostatin, Discodermolide and Taxol

    OpenAIRE

    Paterson, Ian; Naylor, Guy J.; Gardner, Nicola M.; Guzmán, Ester; Wright, Amy E.

    2010-01-01

    The design, synthesis and biological evaluation of a series of hybrids and analogues of the microtubule-stabilising anticancer agents dictyostatin, discodermolide and taxol is described. A 22-membered macrolide scaffold was prepared by adapting earlier synthetic routes directed towards dictyostatin and discodermolide, taking advantage of the distinctive structural and stereochemical similarities between these two polyketide-derived marine natural products. Initial endeavours towards accessing...

  18. Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from Lactobacillus plantarum and identification of its ability to signal through Mincle.

    Science.gov (United States)

    Shah, Sayali; Nagata, Masahiro; Yamasaki, Sho; Williams, Spencer J

    2016-09-18

    We report a concise synthesis of glycolipid GL1 from Lactobacillus plantarum commencing from methyl α-d-glucopyroside. A Jacobsen hydrolytic kinetic resolution is used to generate a diastereomerically-pure glycidyl glucoside that was elaborated to the diglyceride by stepwise brominolysis, acylation with oleoyl chloride, and bromide-substitution by the tetrabutylammonium salt of 9S,10R-dihydrosterculic acid. GL1 and analogues were shown to signal through the glycolipid pattern recognition receptor Mincle. PMID:27533919

  19. Models and prototypes of biomimetic devices to architectural purposes

    Directory of Open Access Journals (Sweden)

    Silvia Titotto

    2014-12-01

    Full Text Available This paper presents some results of an ongoing interdisciplinary research about models and prototypes of biomimetic devices via installations and the focus of this paper is to outline this research role in architectural purposes as it perpasses the cultural and heritage contexts by being a way of understanding and living in the world as well as taking place in the world as devices or environments that pass on to future generations to use, learn from and be inspired by. Both the theoretical and the experimental work done so far point out that installations built with association of laser cutting and rapid prototyping techniques might be on the best feasible ways for developing and testing new technologies involved in biomimetic devices to architectural purposes that put both tectonics and nature as their central theme. 

  20. Biomimetic Adhesive Materials Containing Cyanoacryl Group for Medical Application

    Directory of Open Access Journals (Sweden)

    Sueng Hwan Jo

    2014-10-01

    Full Text Available For underwater adhesives with biocompatible and more flexible bonds using biomimetic adhesive groups, DOPA-like adhesive molecules were modified with cyanoacrylates to obtain different repeating units and chain length copolymers. The goal of this work is to copy the mechanisms of underwater bonding to create synthetic water-borne underwater medical adhesives through blending of the modified DOPA and a triblock copolymer (PEO-PPO-PEO for practical application to repair wet living tissues and bones, and in turn, to use the synthetic adhesives to test mechanistic hypotheses about the natural adhesive. The highest values in stress and modulus of the biomimetic adhesives prepared in wet state were 165 kPa and 33 MPa, respectively.

  1. Surface Modifications of Support Partitions for Stabilizing Biomimetic Membrane Arrays

    DEFF Research Database (Denmark)

    Perry, Mark; Hansen, Jesper Schmidt; Jensen, Karin Bagger Stibius;

    2011-01-01

    Black lipid membrane (BLM) formation across apertures in an ethylene tetra-fluoroethylene (ETFE) partition separating two aqueous compartments is an established technique for the creation of biomimetic membranes. Recently multi-aperture BLM arrays have attracted interest and in order to increase...... with a high signal-to-noise (s/n) ratio. We demonstratesd this by reconstituting gA and α-hemolysin (α-HL) into BLM arrays. The improvement in membrane array lifetime and s/n ratio demonstrates that surface plasma polymerization of the supporting partition can be used to increase the stability of biomimetic...... BLM array stability we studied the effect of covalently modifying the partition substrate using surface plasma polymerization with hydrophobic n-hexene, 1-decene and hexamethyldisiloxane (HMDSO) as modification groups. Average lifetimes across singlesided HMDSO modified partitions or using 1-decene...

  2. Sensing in nature: using biomimetics for design of sensors

    DEFF Research Database (Denmark)

    Lenau, Torben Anker; Cheong, Hyunmin; Shu, Li

    2008-01-01

    of sense organs in animals and illustrates how a formal search method developed at University of Toronto can be applied to sensor design. Design/methodology/approach – Using biomimetics involves a search for relevant cases, a proper analysis of the biological solutions, identification of design principles...... and design of the desired artefact. The present search method is based on formulation of relevant keywords and search for occurrences in a standard university biology textbook. Most often a simple formulation of keywords and a following search is not enough to generate a sufficient amount of useful ideas...... or the search gives too many results. This is handled by a more advanced search strategy where the search is either widened or it is focused further mainly using biological synonyms. Findings – A major problem in biomimetic design is finding the relevant analogies to actual design tasks in nature. Research...

  3. Design of biomimetic camouflage materials based on angiosperm leaf organs

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    The micro structures and reflectance spectra of angiosperm leaves were compared with those of angiosperm petals. The study indicated that angiosperm leaf organs had identical micro structures and reflectance characteristics in the wave band of near infrared. Micro structures and compositions of leaf organs were the crucial factors influencing their reflectance spectra. The model of biomimetic materials based on angiosperm leaf organs was introduced and verified. From 300 to 2600 nm, the similarity coefficients of reflectance spectra of the foam containing water and Platanus Orientalis Linn. leaves were all above 0.969. The biomimetic camou- flage material exhibited almost the same reflectance spectra with those of green leaves in ultraviolet, visible and near infrared wave bands. And its "concolor and conspectrum" effect might take on reconnaissance of hyperspectral and ultra hy- perspectral imaging.

  4. Methods for biomimetic remineralization of human dentine: A systematic review

    OpenAIRE

    Chris Ying Cao; May Lei Mei; Quan-Li Li; Edward Chin Man Lo; Chun Hung Chu

    2015-01-01

    This study aimed to review the laboratory methods on biomimetic remineralization of demineralized human dentine. A systematic search of the publications in the PubMed, TRIP, and Web of Science databases was performed. Titles and abstracts of initially identified publications were screened. Clinical trials, reviews, non-English articles, resin-dentine interface studies, hybrid layer studies, hybrid scaffolds studies, and irrelevant studies were excluded. The remaining papers were retrieved wi...

  5. Biomimetics in Modern Organizations – Laws or Metaphors?

    OpenAIRE

    Markus Schatten; Miroslav Zugaj

    2011-01-01

    Biomimetics, the art and science of imitating nature and life for technological solutions is discussed from a modern organization theory perspective. The main hypothesis of this article is that there are common laws in nature that are applicable to living, social and likewise organizational systems. To take advantage of these laws, the study of nature's principles for their application to organizations is proposed - a process which is in product and technology design known as bionic creativit...

  6. Biomimetic supramolecular metallohosts for binding and activation of dioxygen

    OpenAIRE

    Sprakel, Vera Stefanie Irene

    2004-01-01

    Host-guest chemistry involves the binding of a specific substrate in a receptor via molecular recognition based on supramolecular interactions. Metal-containing derivatives of receptors for the selective supramolecular binding of dihydroxybenzene substrates, which receptors model oxygen binding enzymes both in structure and in function are described in this thesis with the ultimate goal to realize biomimetic catalysis. A PY2-appended receptor 1 and a TPA-appended receptor 2 and the bis-copper...

  7. Biomimetic Crawling Motion of Soft and Slender Gel-worm

    Institute of Scientific and Technical Information of China (English)

    Song Miao LIANG; Jian XU; Li Na ZHANG

    2006-01-01

    Inspired by the locomotion of terrestrial limbless animals, the present work attempt to study the motion of biomimetic system based on poly(vinyl alcohol)/dimethylsulfoxide gel. The system was operated in air by employing a non-contacted DC electric field. The results showed that the gel exhibited a long-range snail-like motion and had a very fast response rate.

  8. Flight mechanism and design of biomimetic micro air vehicles

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    This paper summaries the investigations on natural flyers and development of bio-mimetic micro air vehicles(MAVs)at NUAA,China,where the authors have led a group to conduct research for a decade. The investigations include the studies of low Reynolds number aerodynamics,unsteady computational fluid dynamics and flight control for the fixed-wing MAVs,the bird-like MAVs,the dragonfly-like MAVs and the bee-like MAVs.

  9. Neural Networks Integrated Circuit for Biomimetics MEMS Microrobot

    OpenAIRE

    Ken Saito; Kazuaki Maezumi; Yuka Naito; Tomohiro Hidaka; Kei Iwata; Yuki Okane; Hirozumi Oku; Minami Takato; Fumio Uchikoba

    2014-01-01

    In this paper, we will propose the neural networks integrated circuit (NNIC) which is the driving waveform generator of the 4.0, 2.7, 2.5 mm, width, length, height in size biomimetics microelectromechanical systems (MEMS) microrobot. The microrobot was made from silicon wafer fabricated by micro fabrication technology. The mechanical system of the robot was equipped with small size rotary type actuators, link mechanisms and six legs to realize the ant-like switching behavior. The NNIC generat...

  10. Flisht mechanism and design of biomimetic micro air vehicles

    Institute of Scientific and Technical Information of China (English)

    ANG HaiSong; XIAO TianHang; DUAN WenBo

    2009-01-01

    This paper summaries the investigations on natural flyers and development of bio-mimetic micro air vehicles(MAVs)at NUAA,China,where the authors have led a group to conduct research for a decade.The investigations include the studies of low Reynolds number aerodynamics,unsteady computational fluid dynamics and flight control for the fixed-wing MAVs,the bird-like MAVs,the dragonfly-like MAVs and the bee-like MAVs.

  11. Aquaporin-Based Biomimetic Polymeric Membranes: Approaches and Challenges

    DEFF Research Database (Denmark)

    Habel, Joachim Erich Otto; Hansen, Michael; Kynde, Søren;

    2015-01-01

    In recent years, aquaporin biomimetic membranes (ABMs) for water separation have gained considerable interest. Although the first ABMs are commercially available, there are still many challenges associated with further ABM development. Here, we discuss the interplay of the main components of ABMs...... thin film interfacial polymerization techniques. Finally, we describe some new developments in interfacial polymerization using polyhedral oligomeric silsesquioxane cages for increasing the physical and chemical durability of thin film composite membranes....

  12. Fabrication of Biomimetic Water Strider Legs Covered with Setae

    Institute of Scientific and Technical Information of China (English)

    Zhi-guo Zhou; Zhi-wen Liu

    2009-01-01

    Water striders have remarkable water-repellent legs that enable them to stand effortlessly and move quickly on water. Fluid physics indicates this feature is due to a surface-tension effect caused by the special hierarchical structure of the legs, which are covered with a large number of inclined setae with fine nanogrooves inducing water resistance. This inspires us to fabricate special water-repellent structure on functional surfaces through the cooperation between the surface treatment and the surface micro- and nanostructures, which may bring great advantages in a wide variety of applications. In this paper we present a procedure for fabricating biomimetic water strider legs covered with setae using Polycarbonate Track-Etched (PCTE) membranes as templates. By choosing appropriate membrane lengths, diameters, pitches and densities of the setae, the biomimetic legs can be fabricated conveniently and at a low cost. Furthermore we investigated the relationship between stiffness of the molding materials, high aspect ratio and density, which affect the fidelity of fabrication and self adhesion, to optimize the stability of setae. The knowledge we gained from this study will offer important insights into the biomimetic design and fabrication of water strider setae.

  13. Biomimetic coating of calcium phosphate on biometallic materials

    Institute of Scientific and Technical Information of China (English)

    ZHANG Er-lin; YANG Ke

    2005-01-01

    The biomimetic coating process in comparison with other processes is reviewed. This processing shows advantages in the surface bio-modification, such as low cost and flexible processing, wide range of apatite composition and thickness, non-line-of-sight characteristic and possibility to coat polymers and porous implants. The bio-mimetic apatite coating is made up of larger number of globules with size of 1-5μm. Each globule is a group of numerous flakes with a size range of 100-200nm to 30μm in length and 0.1-1μm in thickness. In-vitro and in-vivo studies show that the biomimetic apatite coating can promote an early and strong bonding to bone or promote the bone in-growth into the porous structure, which will be beneficial to the cementless stable fixation of orthopaedic implants. Recently developed co-precipitation of a kind of protein molecules into the HA coating shows much promising.

  14. Total Synthesis of Sarcophytonolide H and Isosarcophytonolide D: Structural Revision of Isosarcophytonolide D and Structure-Antifouling Activity Relationship of Sarcophytonolide H.

    Science.gov (United States)

    Takamura, Hiroyoshi; Kikuchi, Takahiro; Endo, Noriyuki; Fukuda, Yuji; Kadota, Isao

    2016-05-01

    The first total syntheses of sarcophytonolide H and the originally proposed and correct structures of isosarcophytonolide D have been achieved via transannular ring-closing metathesis (RCM). These total syntheses culminated in the stereostructural confirmation of sarcophytonolide H and the reassignment of isosarcophytonolide D, respectively. The antifouling activity of the synthetic sarcophytonolide H and its analogues was also evaluated. PMID:27093115

  15. The first total synthesis of ganglioside GalNAc-GD1a, a target molecule for autoantibodies in Guillain-Barré syndrome.

    Science.gov (United States)

    Fujikawa, Kohki; Nakashima, Shinya; Konishi, Miku; Fuse, Tomoaki; Komura, Naoko; Ando, Takayuki; Ando, Hiromune; Yuki, Nobuhiro; Ishida, Hideharu; Kiso, Makoto

    2011-05-01

    The first synthesis of ganglioside GalNAc-GD1a, featuring efficient glycan assembly and a cyclic glucosyl ceramide as a versatile unit for ganglioside synthesis is described. Although ganglioside GalNAc-GD1a was first found as a brain ganglioside, IgG autoantibodies to GalNAc-GD1a were subsequently found to be closely related to a human peripheral-nerve disorder, Guillain-Barré syndrome, which is the commonest cause of acute flaccid paralysis worldwide. In this study, the characteristic hexasaccharide part carrying two sialic acid residues was synthesized efficiently by use of a readily accessible GM2-core unit as a common unit. The potentially difficult coupling of the oligosaccharide and ceramide moieties was carried out by using a cyclic glucosyl ceramide as a coupling partner for the hexasaccharide part, thereby successfully providing the framework of the target compound. Global deprotection delivered the homogenous ganglioside GalNAc-GD1a. An enzyme-linked immunosorbent assay showed that sera from patients with Guillain-Barré syndrome reacted both with natural and with synthetic GalNAc-GD1a.

  16. The first total synthesis of ganglioside GalNAc-GD1a, a target molecule for autoantibodies in Guillain-Barré syndrome.

    Science.gov (United States)

    Fujikawa, Kohki; Nakashima, Shinya; Konishi, Miku; Fuse, Tomoaki; Komura, Naoko; Ando, Takayuki; Ando, Hiromune; Yuki, Nobuhiro; Ishida, Hideharu; Kiso, Makoto

    2011-05-01

    The first synthesis of ganglioside GalNAc-GD1a, featuring efficient glycan assembly and a cyclic glucosyl ceramide as a versatile unit for ganglioside synthesis is described. Although ganglioside GalNAc-GD1a was first found as a brain ganglioside, IgG autoantibodies to GalNAc-GD1a were subsequently found to be closely related to a human peripheral-nerve disorder, Guillain-Barré syndrome, which is the commonest cause of acute flaccid paralysis worldwide. In this study, the characteristic hexasaccharide part carrying two sialic acid residues was synthesized efficiently by use of a readily accessible GM2-core unit as a common unit. The potentially difficult coupling of the oligosaccharide and ceramide moieties was carried out by using a cyclic glucosyl ceramide as a coupling partner for the hexasaccharide part, thereby successfully providing the framework of the target compound. Global deprotection delivered the homogenous ganglioside GalNAc-GD1a. An enzyme-linked immunosorbent assay showed that sera from patients with Guillain-Barré syndrome reacted both with natural and with synthetic GalNAc-GD1a. PMID:21469228

  17. MGF-Ct24E改性聚乳酸的合成、表征及其对成骨细胞增殖的评价%Synthesis, characterization and osteoblasts proliferation of a novel biomimetic material based on MGF-Ct24E modified poly (D, L-lactic acid)

    Institute of Scientific and Technical Information of China (English)

    罗嘉; 李玉筱; 王品品; 王远亮

    2013-01-01

    力生长因子(MGF)是骨修复重建的一种重要生长因子.以二环己基碳二亚胺为缩合剂,将MGF羧基端E结构域24肽(MGF-Ct24E)共价接枝到丁二胺改性的聚乳酸上(DPLA),制得了新型MGF-Ct24E改性聚乳酸仿生材料(MGF Ct24E-DPLA).采用氨基酸分析和高效液相色谱对MGF-Ct24E含量进行了定性定量表征,静态水接触角和吸水率测定了MGF-Ct24E DPLA材料的亲水性,MTT法评价了其对成骨细胞的增殖作用.结果表明,MGF-Ct24E成功引入到DPLA中,接枝效率为24.7%,并且和DPLA相比,MGF-Ct24E-DPLA材料具有更好的亲水性和促进成骨细胞增殖的能力.因此这种新型MGF-Ct24E改性聚乳酸仿生材料有望成为骨组织工程领域中一种卓越的生物材料.%Mechano-growth factor (MGF) is one of the most important growth factors of bone regeneration. A novel biomimetic poly (D, L-lactic acid) (PDLLA) modification was designed and synthesized based on MGF-Ct24E grafted butanediamine modified PDLLA (DPLA). MGF-Ct24Es were grafted into the side chain of DP-LA via a stable covalent amide bond by using dicyclohexylcarbodiimide (DCC) as the condensing agent to produce biomimetic DPLA materials (MGF-Ct24E-DPLA). Amino acid analyzer (AAA) and high performance liquid chromatography (HPLC) were used to characterize the MGF-Ct24E-DPLA. The hydrophilicity of MGF-Ct24E-DPLA was evaluated by means of the water-uptake ratios and static water contact angle. Data revealed that the grafting efficiency of MGF-Ct24E was about 24. 7%. MGF-Ct24E-MPLA had better hydrophilicity than DPLA. The osteoblasts behavior of proliferation, on glass, DPLA and MGF-Ct24E-DPLA films was investigated and the results indicated that the introduction of MGF-Ct24E could improve osteoblasts proliferation. The MGF-Ct24EMPLA with higher bioactivity may have potential application for bone tissue engineering.

  18. Plants and Animals as Concept Generators for the Development of Biomimetic Cable Entry Systems

    Institute of Scientific and Technical Information of China (English)

    Tom Masseiter; Uwe Scharf; Thomas Speck

    2008-01-01

    Many animals and plants have high potential to serve as concept generators for developing biomimetic materials and structures. We present some ideas based on structural and functional properties of plants and animals that led to the development of two types of biomimetic cable entry systems. Those systems have been realized on the level of functional demonstrators.

  19. A future of living machines?: International trends and prospects in biomimetic and biohybrid systems

    Science.gov (United States)

    Prescott, Tony J.; Lepora, Nathan; Vershure, Paul F. M. J.

    2014-03-01

    Research in the fields of biomimetic and biohybrid systems is developing at an accelerating rate. Biomimetics can be understood as the development of new technologies using principles abstracted from the study of biological systems, however, biomimetics can also be viewed from an alternate perspective as an important methodology for improving our understanding of the world we live in and of ourselves as biological organisms. A biohybrid entity comprises at least one artificial (engineered) component combined with a biological one. With technologies such as microscale mobile computing, prosthetics and implants, humankind is moving towards a more biohybrid future in which biomimetics helps us to engineer biocompatible technologies. This paper reviews recent progress in the development of biomimetic and biohybrid systems focusing particularly on technologies that emulate living organisms—living machines. Based on our recent bibliographic analysis [1] we examine how biomimetics is already creating life-like robots and identify some key unresolved challenges that constitute bottlenecks for the field. Drawing on our recent research in biomimetic mammalian robots, including humanoids, we review the future prospects for such machines and consider some of their likely impacts on society, including the existential risk of creating artifacts with significant autonomy that could come to match or exceed humankind in intelligence. We conclude that living machines are more likely to be a benefit than a threat but that we should also ensure that progress in biomimetics and biohybrid systems is made with broad societal consent.

  20. Total algorithms

    NARCIS (Netherlands)

    Tel, G.

    1993-01-01

    We define the notion of total algorithms for networks of processes. A total algorithm enforces that a "decision" is taken by a subset of the processes, and that participation of all processes is required to reach this decision. Total algorithms are an important building block in the design of distri

  1. Biomimetics in materials science self-healing, self-lubricating, and self-cleaning materials

    CERN Document Server

    Nosonovsky, Michael

    2012-01-01

    Biomimetics in Materials Science provides a comprehensive theoretical and practical review of biomimetic materials with self-healing, self-lubricating and self-cleaning properties. These three topics are closely related and constitute rapidly developing areas of study. The field of self-healing materials requires a new conceptual understanding of this biomimetic technology, which is in contrast to traditional  engineering processes such as wear and fatigue.  Biomimetics in Materials Science is the first monograph to be devoted to these materials. A new theoretical framework for these processes is presented based on the concept of multi-scale structure of entropy and non-equilibrium thermodynamics, together with a detailed review of the available technology. The latter includes experimental, modeling, and simulation results obtained on self-healing/lubricating/cleaning materials since their emergence in the past decade. Describes smart, biomimetic materials in the context of nanotechnology, biotechnology, an...

  2. Biomimetic design of a bacterial cellulose/hydroxyapatite nanocomposite for bone healing applications

    International Nuclear Information System (INIS)

    This study describes the design and synthesis of bacterial cellulose/hydroxyapatite nanocomposites for bone healing applications using a biomimetic approach. Bacterial cellulose (BC) with various surface morphologies (pellicles and tubes) was negatively charged by the adsorption of carboxymethyl cellulose (CMC) to initiate nucleation of calcium-deficient hydroxyapatite (cdHAp). The cdHAp was grown in vitro via dynamic simulated body fluid (SBF) treatments over a one week period. Characterization of the mineralized samples was done with X-ray Photoelectron Spectroscopy (XPS) and Field Emission Scanning Electron Microscopy (FESEM) with Energy Dispersive Spectroscopy (EDS). The amount of cdHAp observed varied among different samples. XPS demonstrated that the atomic presence of calcium and phosphorus ranged from 0.44 at.% to 7.71 at.% Ca and 0.27 at.% to 11.18 at.% P. The Ca/P overall ratio ranged from 1.22 to 1.92. FESEM images showed that the cdHAp crystal size increased with increasing nanocellulose fibril density. To determine the viability of the scaffolds in vitro, the morphology and differentiation of osteoprogenitor cells was analyzed using fluorescence microscopy and alkaline phosphatase gene expression. The presence of cdHAp crystals on BC surfaces resulted in increased cell attachment.

  3. Biomimetic design of a bacterial cellulose/hydroxyapatite nanocomposite for bone healing applications

    Energy Technology Data Exchange (ETDEWEB)

    Zimmermann, Kristen A., E-mail: kazimmer@vt.edu [Department of Materials Science and Engineering, Virginia Tech, Blacksburg, VA 24060 (United States); School of Biomedical Engineering Sciences, Virginia Tech, Blacksburg, VA 24060 (United States); LeBlanc, Jill M.; Sheets, Kevin T.; Fox, Robert W. [Department of Materials Science and Engineering, Virginia Tech, Blacksburg, VA 24060 (United States); Gatenholm, Paul [Department of Materials Science and Engineering, Virginia Tech, Blacksburg, VA 24060 (United States); School of Biomedical Engineering Sciences, Virginia Tech, Blacksburg, VA 24060 (United States)

    2011-01-01

    This study describes the design and synthesis of bacterial cellulose/hydroxyapatite nanocomposites for bone healing applications using a biomimetic approach. Bacterial cellulose (BC) with various surface morphologies (pellicles and tubes) was negatively charged by the adsorption of carboxymethyl cellulose (CMC) to initiate nucleation of calcium-deficient hydroxyapatite (cdHAp). The cdHAp was grown in vitro via dynamic simulated body fluid (SBF) treatments over a one week period. Characterization of the mineralized samples was done with X-ray Photoelectron Spectroscopy (XPS) and Field Emission Scanning Electron Microscopy (FESEM) with Energy Dispersive Spectroscopy (EDS). The amount of cdHAp observed varied among different samples. XPS demonstrated that the atomic presence of calcium and phosphorus ranged from 0.44 at.% to 7.71 at.% Ca and 0.27 at.% to 11.18 at.% P. The Ca/P overall ratio ranged from 1.22 to 1.92. FESEM images showed that the cdHAp crystal size increased with increasing nanocellulose fibril density. To determine the viability of the scaffolds in vitro, the morphology and differentiation of osteoprogenitor cells was analyzed using fluorescence microscopy and alkaline phosphatase gene expression. The presence of cdHAp crystals on BC surfaces resulted in increased cell attachment.

  4. Optimizing the Production of Biodiesel Using Lipase Entrapped in Biomimetic Silica

    Directory of Open Access Journals (Sweden)

    Chi-Yang Yu

    2013-04-01

    Full Text Available We entrapped lipase from Pseudomonas cepacia in polyallylamine-mediated biomimetic silica, and then applied entrapped lipase to the synthesis of biodiesel with soybean oil or waste cooking oil as a feedstock. The effects of reaction temperature, substrate molar ratio (methanol/oil and n-hexane content (w/w of oil were evaluated using response surface methodology (RSM combined with Box-Behnken design. The optimal reaction conditions for soybean oil were 43.6 °C, substrate molar ratio of 4.3%, and 75% n-hexane. The predicted and experimental values of biodiesel conversion were 79% and 76%, respectively. The optimal reaction conditions for waste cooking oil were 43.3 °C, substrate molar ratio of 5%, and 38% n-hexane. The predicted and experimental values of conversion were 68% and 67%, respectively. The conversion efficiency remained the same even after 1-month storage of entrapped lipase at 4 °C or room temperature.

  5. Biomimetic Catalysts for Oxidation of Veratryl Alcohol, a Lignin Model Compound

    Directory of Open Access Journals (Sweden)

    Marcelino Maneiro

    2013-03-01

    Full Text Available Kraft pulp has to be bleached to eliminate the chromophoric structures, which cause a darkening of the pulp. In Nature, an equivalent role is assumed by ligninolytic enzymes such as lignin peroxidases, manganese peroxidases and laccases. The development of low molecular weight manganese peroxidase mimics may achieve environmentally-safe bleaching catalysts for the industry. Herein we report the synthesis and characterization of six manganese(III complexes 1–6, incorporating dianionic hexadentate Schiff base ligands (H2L1-H2L4 and different anions. Complex 4, Mn2L22(H2O2(DCA2 was crystallographically characterized. Complexes 1–4 behave as more efficient mimics of peroxidase in contrast to 5–6. We have studied the use of these complexes as catalysts for the degradation of the lignin model compound veratryl alcohol. The biomimetic catalysts were used in conjunction with chlorine-free inexpensive co-oxidants as dioxygen or hydrogen peroxide. Yields up to 30% of veratryl alcohol conversion to veratraldehyde have been achieved at room temperature in presence of air flow using 0.5% of catalyst.

  6. Ultra-Porous Nanoparticle Networks: A Biomimetic Coating Morphology for Enhanced Cellular Response and Infiltration

    Science.gov (United States)

    Nasiri, Noushin; Ceramidas, Anthony; Mukherjee, Shayanti; Panneerselvan, Anitha; Nisbet, David R.; Tricoli, Antonio

    2016-01-01

    Orthopedic treatments are amongst the most common cause of surgery and are responsible for a large share of global healthcare expenditures. Engineering materials that can hasten bone integration will improve the quality of life of millions of patients per year and reduce associated medical costs. Here, we present a novel hierarchical biomimetic coating that mimics the inorganic constituent of mammalian bones with the aim of improving osseointegration of metallic implants. We exploit the thermally-driven self-organization of metastable core-shell nanoparticles during their aerosol self-assembly to rapidly fabricate robust, ultra-porous nanoparticle networks (UNN) of crystalline hydroxyapatite (HAp). Comparative analysis of the response of osteoblast cells to the ultra-porous nanostructured HAp surfaces and to the spin coated HAp surfaces revealed superior osseointegrative properties of the UNN coatings with significant cell and filopodia infiltration. This flexible synthesis approach for the engineering of UNN HAp coatings on titanium implants provides a platform technology to study the bone-implant interface for improved osseointegration and osteoconduction. PMID:27076035

  7. Rapid biomimetic deposition of octacalcium phosphate coatings on zirconia ceramics (Y-TZP) for dental implant applications

    Science.gov (United States)

    Stefanic, Martin; Krnel, Kristoffer; Pribosic, Irena; Kosmac, Tomaz

    2012-03-01

    Octacalcium phosphate (OCP) coatings on zirconia oral implants have a great potential to improve the osseointegration of already existing ceramic implants, owing to high osteoconductive characteristics of OCP and its possibility of use as a drug delivery system. Such OCP coatings can be prepared with a simple two-step biomimetic procedure investigated in our study. In the first step, zirconia discs were immersed into the solution with a pH 7.4 and after 1 h of soaking a thin nanostructured calcium phosphate (Ca-P) layer was precipitated on the ceramic substrate via three stages: (i) precipitation of an amorphous Ca-P; (ii) precipitation of the OCP; and (iii) the transformation of the OCP to apatite. This Ca-P layer later served as a template for the rapid deposition of a thicker OCP coating in the second step of the synthesis where the substrate was immersed into the solution with pH 7.0. The main benefits of the method are a relatively quick synthesis, simplicity and a good reproducibility. Moreover, the coatings show good tensile adhesion strength according to the tape tests (ASTM D-3359). In addition, mild physiological conditions of the synthesis may allow incorporation of biologically active molecules in the coating.

  8. Biomimetic oxidation studies. 9. Mechanistic aspects of the oxidation of alcohols with functional,active site methane monooxygenase enzyme models in aqueous solution

    Energy Technology Data Exchange (ETDEWEB)

    Rabion, A. [Lawrence Berkeley National Lab., CA (United States)]|[Univ. of California, Berkeley, CA (United States)]|[Groupement de Recherche de Lacq, Artix (France); Chen, S.; Wang, J.; Buchanan, R.M. [Univ. of Louisville, KY (United States); Seris, J.L. [Groupement de recherche de Lacq, Artix (France); Fish, R.H. [Lawrence Berkeley National Lab., CA (United States)]|[Univ. of California, Berkeley, CA (United States)

    1995-12-13

    The syntheses of biomimetic complexes that mimic the major structural features of the hydroxylase component of methane monooxygenase enzyme (MMO) and, more importantly, that provide similar alkane functionalization activity, in the presence of an oxidant, have been of great interest to the discipline of bioinorganic chemistry. In this communication, we will demonstrate the feasibility of conducting biomimetic oxidation studies in H{sub 2}O with soluble substrates, i.e., alcohols (cyclohexanol, benzyl alcohol), using H{sub 2}O-stable MMO mimics at pH 4.2, and the oxidant, tert-butyl hydroperoxide (TBHP). Both the Mitusunobu procedure and the mesylate displacement reaction proceeded with complete inversion of the stereo-center and provided optically pure penultimate intermediate (>99.9% ee). The synthesis was completed by reduction of the nitro group under standard conditions to deliver LY300164 in 87%. In summary, we have developed an efficient and environmentally benign synthesis of the 5H-2,3-benzodiazepine LY300164 that provides the optically pure compound in 51% overall yield. Intramolecular hydrazone alkylation led to a remarkably facile and selective formation of the benzodiazepine. Furthermore, the application of resins to whole-cell-based biotransformations should find general utility for similar reactions that are complicated by component inhibition and product isolation. 11 refs., 1 fig.

  9. First Total Synthesis of 4,5-Secoeudesmane-type and Iphionane-type Compounds- Synthesis of 4,5-Dioxo-seco-γ-eudesmol and 5β ,11-Dihydroxyiphionan-4-one

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    @@ 4, 5-Secoeudesmane-type and iphionane-type compounds are sesquiterpenes with new carbon skeletons found in natrual sources in recent years.1-6 The co-occurence of 4, 5-secoeudesmanes, iphionanes and eudesmanes as natrual products suggests that 4, 5-secoeudesmanes, iphionanes most likely are generated biogenetically from eudesmanes, and iphionanes are formed biogenetically by aldol reaction of 4, 5-dioxosecoeudesmanes1,4,6,7. The study on the synthesis of this two kind of new sesquiterpenes has not been reported in the literature.

  10. Anti-wear properties on 20CrMnTi steel surfaces with biomimetic non-smooth units

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    In order to gain a sufficient wear resistance for applications, the biomimetic non-smooth units in concave were fabricated on the surfaces of 20CrMnTi steel using a biomimetic laser remelting technology. The diameter and distribution of the concaves were optimized using orthogonal experiment. The microstructures of the biomimetic non-smooth units were examined. The anti-wear behaviors were investigated by the rolling wear test with lubricant. The results of wear tests indicated that the biomimetic surfaces exhibit a higher anti-wear ability than the smooth surfaces. The biomimetic surface with concaves of 250 μm in diameter and transverse distance of 270 μm and longitudinal distance of 400 μm exhibits the best anti-wear property. The enhancement of wear resistance can be mainly attributed to the action of biomimetic non-smooth units and the super fined microstructure and hardness in the biomimetic unit zones.

  11. Manipulation of biomimetic objects in acoustic levitation

    OpenAIRE

    Castro, Angelica

    2013-01-01

    This thesis contains 9 chapters making a total of 205 pages including articles. The articles are menctioned throughout the work and are listed as annexes. These articles were produced during the PhD.; Levitation is a promising tool for contactless guiding and non-toxic manipulation. Acoustic levitation by ultrasonic standing waves (USW) allows micron-scale particle manipulation in acoustic resonators. The main goal of this thesis is to explore the possibilities given by the acoustic levitatio...

  12. Modular Terpenoid Construction via Catalytic Enantioselective Formation of All-Carbon Quaternary Centers: Total Synthesis of Oridamycin A, Triptoquinones B and C, and Isoiresin.

    Science.gov (United States)

    Feng, Jiajie; Noack, Florian; Krische, Michael J

    2016-09-28

    Total syntheses of oridamycin A, triptoquinones B and C, and isoiresin are accomplished from a common intermediate prepared via iridium-catalyzed alcohol C-H tert-(hydroxy)prenylation - a byproduct-free process that forms an all-carbon quaternary stereocenter with excellent control of diastereo- and enantioselectivity.

  13. A biomimetic methane-oxidising catalyst

    Energy Technology Data Exchange (ETDEWEB)

    Dalton, H. [Warwick Univ., Coventry (United Kingdom). Dept. of Biological Sciences

    1996-12-31

    The diminishing resources of petroleum oil has meant that there has been considerable efforts in recent years to find a suitable substitute for gasoline as a transportation fuel. Methanol has been identified as a suitable substitute since it is a readily combustible fuel which can be manufactured from a number of different sources. Methane is commonly used as a starting material for the production of synthesis gas (CO + H{sub 2}) and hence methanol. It is well known that the cleavage of the C-H bond of methane is extremely difficult (bond energy is around 104 kcal/mol) and that fairly drastic conditions are required to convert methane into methanol. Temperatures around 1200 deg C and pressures of up to 100 atmospheres over metal catalysts in a series of reactions are required to effect this process. Efforts have been made to reduce the temperature and the number of steps by using lanthanide ruthenium oxide catalyst but such reactions are still thermodynamically endothermic. An energetically more efficient reaction would be the direct conversion of methane to methanol using oxygen as the oxidant: CH{sub 4} + 1/2O{sub 2} -> CH{sub 3}OH {Delta}H deg = - 30.7 kcal/mol. Such a direct oxidation route is manifest in the bacterially-mediated oxidation of methane by methanotrophic bacteria. These organisms effect the direct oxidation of methane to methanol by the enzyme methane monooxygenase (MMO) as part of the reaction sequences to oxidize methane to carbon dioxide. (14 refs.)

  14. A novel soft biomimetic microrobot with two motion attitudes.

    Science.gov (United States)

    Shi, Liwei; Guo, Shuxiang; Li, Maoxun; Mao, Shilian; Xiao, Nan; Gao, Baofeng; Song, Zhibin; Asaka, Kinji

    2012-01-01

     A variety of microrobots have commonly been used in the fields of biomedical engineering and underwater operations during the last few years. Thanks to their compact structure, low driving power, and simple control systems, microrobots can complete a variety of underwater tasks, even in limited spaces. To accomplish our objectives, we previously designed several bio-inspired underwater microrobots with compact structure, flexibility, and multi-functionality, using ionic polymer metal composite (IPMC) actuators. To implement high-position precision for IPMC legs, in the present research, we proposed an electromechanical model of an IPMC actuator and analysed the deformation and actuating force of an equivalent IPMC cantilever beam, which could be used to design biomimetic legs, fingers, or fins for an underwater microrobot. We then evaluated the tip displacement of an IPMC actuator experimentally. The experimental deflections fit the theoretical values very well when the driving frequency was larger than 1 Hz. To realise the necessary multi-functionality for adapting to complex underwater environments, we introduced a walking biomimetic microrobot with two kinds of motion attitudes: a lying state and a standing state. The microrobot uses eleven IPMC actuators to move and two shape memory alloy (SMA) actuators to change its motion attitude. In the lying state, the microrobot implements stick-insect-inspired walking/rotating motion, fish-like swimming motion, horizontal grasping motion, and floating motion. In the standing state, it implements inchworm-inspired crawling motion in two horizontal directions and grasping motion in the vertical direction. We constructed a prototype of this biomimetic microrobot and evaluated its walking, rotating, and floating speeds experimentally. The experimental results indicated that the robot could attain a maximum walking speed of 3.6 mm/s, a maximum rotational speed of 9°/s, and a maximum floating speed of 7.14 mm/s. Obstacle

  15. A Novel Soft Biomimetic Microrobot with Two Motion Attitudes

    Directory of Open Access Journals (Sweden)

    Liwei Shi

    2012-12-01

    Full Text Available  A variety of microrobots have commonly been used in the fields of biomedical engineering and underwater operations during the last few years. Thanks to their compact structure, low driving power, and simple control systems, microrobots can complete a variety of underwater tasks, even in limited spaces. To accomplish our objectives, we previously designed several bio-inspired underwater microrobots with compact structure, flexibility, and multi-functionality, using ionic polymer metal composite (IPMC actuators. To implement high-position precision for IPMC legs, in the present research, we proposed an electromechanical model of an IPMC actuator and analysed the deformation and actuating force of an equivalent IPMC cantilever beam, which could be used to design biomimetic legs, fingers, or fins for an underwater microrobot. We then evaluated the tip displacement of an IPMC actuator experimentally. The experimental deflections fit the theoretical values very well when the driving frequency was larger than 1 Hz. To realise the necessary multi-functionality for adapting to complex underwater environments, we introduced a walking biomimetic microrobot with two kinds of motion attitudes: a lying state and a standing state. The microrobot uses eleven IPMC actuators to move and two shape memory alloy (SMA actuators to change its motion attitude. In the lying state, the microrobot implements stick-insect-inspired walking/rotating motion, fish-like swimming motion, horizontal grasping motion, and floating motion. In the standing state, it implements inchworm-inspired crawling motion in two horizontal directions and grasping motion in the vertical direction. We constructed a prototype of this biomimetic microrobot and evaluated its walking, rotating, and floating speeds experimentally. The experimental results indicated that the robot could attain a maximum walking speed of 3.6 mm/s, a maximum rotational speed of 9°/s, and a maximum floating speed of 7

  16. 应用SMARTercDNA合成技术扩增落地生根叶片的总RNA%Total RNA Amplification from Leaves of Kalanchoe daigremontiana Using SMARTer cDNA Synthesis Technology

    Institute of Scientific and Technical Information of China (English)

    钟天秀; 曾会明

    2011-01-01

    以落地生根(Kalanchoe daigremontiana)未长芽和长芽的叶片为材料,提取落地生根的总RNA,采用SMARTer cDNA合成技术合成cDNA第1链,优化扩增第2链,通过设置梯度PCR扩增循环数,电泳分析后鉴定cDNA质量.结果表明:未长芽和长芽的材料各1μg总RNA分别成功扩增质量较高的双链cDNA.此方法的应用解决了研究材料有限的问题,可由微量的总RNA扩增出足够多的高质量双链cDNA,为进一步从基因水平研究落地生根奠定基础.%Total RNA was extracted from Kalanchoe daigremontiana leaves with or without bulbiferous spurs. The first-strand of cDNA synthesis and the double-strands cDNA amplification were performed u-sing super SMARTer cDNA synthesis technology. The quality of cDNA was evaluated through the gradient of PCR amplification cycles and electrophoresis. High quality double-strands cDNA were obtained from 1 ug total RNA. This method can solve the problem of limited research materials as sufficient high-quality double-strands cDNA are obtained from small amounts of total RNA. This technique allows further research of Kalanchoe daigremontiana.

  17. Polycyclic Polyprenylated Xanthones from Symphonia globulifera: Isolation and Biomimetic Electrosynthesis.

    Science.gov (United States)

    Cottet, Kevin; Neudörffer, Anne; Kritsanida, Marina; Michel, Sylvie; Lallemand, Marie-Christine; Largeron, Martine

    2015-08-28

    Two regioisomeric polycyclic xanthones, 3,16-oxyguttiferone A (2) and 1,16-oxyguttiferone A (3), which are polyprenylated acylphloroglucinol-derived analogues, were isolated from the seeds of Symphonia globulifera, together with their presumed o-dihydroxybenzoyl precursor, guttiferone A (1). Anodic oxidation of 1 into the corresponding o-quinone species proved to be an efficient biomimetic method to generate xanthones 2 and 3 in high overall yield and to confirm their structures. Both compounds displayed cytotoxicity against the HCT 116 colon carcinoma cell line with IC₅₀ values of 8 and 3 μM, respectively. PMID:26221771

  18. Touch stimulated pulse generation in biomimetic single-layer graphene

    Science.gov (United States)

    Sul, Onejae; Chun, Hyunsuk; Choi, Eunseok; Choi, Jungbong; Cho, Kyeongwon; Jang, Dongpyo; Chun, Sungwoo; Park, Wanjun; Lee, Seung-Beck

    2016-02-01

    Detecting variation in contact pressure is a separate sensing mode in the human somatosensory system that differs from the detection of pressure magnitude. If pressure magnitude and variation sensing can be achieved simultaneously, an advanced biomimetic tactile system that better emulates human senses may be developed. We report on a novel single-layer graphene based artificial mechanoreceptor that generates a resistance pulse as the contact stimulus passes a specific threshold pressure, mimicking the generation of action potentials in a biological fast-adapting mechanoreceptor. The electric field from a flexible membrane gate electrode placed above a graphene channel raises the Fermi level from the valence band as pressure deflects the membrane. The threshold pressure is reached when the Fermi level crosses the Dirac point in the graphene energy band, which generates a sharp peak in the measured resistance. We found that by changing the gate potential it was possible to modulate the threshold pressure and using a series of graphene channels, a train of pulses were generated during a transient pressurizing stimulus demonstrating biomimetic behaviour.Detecting variation in contact pressure is a separate sensing mode in the human somatosensory system that differs from the detection of pressure magnitude. If pressure magnitude and variation sensing can be achieved simultaneously, an advanced biomimetic tactile system that better emulates human senses may be developed. We report on a novel single-layer graphene based artificial mechanoreceptor that generates a resistance pulse as the contact stimulus passes a specific threshold pressure, mimicking the generation of action potentials in a biological fast-adapting mechanoreceptor. The electric field from a flexible membrane gate electrode placed above a graphene channel raises the Fermi level from the valence band as pressure deflects the membrane. The threshold pressure is reached when the Fermi level crosses the Dirac

  19. UV photofunctionalization promotes nano-biomimetic apatite deposition on titanium

    Directory of Open Access Journals (Sweden)

    Saita M

    2016-01-01

    Full Text Available Makiko Saita,1 Takayuki Ikeda,1,2 Masahiro Yamada,1,3 Katsuhiko Kimoto,4 Masaichi Chang-Il Lee,5 Takahiro Ogawa1 1Division of Advanced Prosthodontics, Weintraub Center for Reconstructive Biotechnology, UCLA School of Dentistry, Los Angeles, CA, USA; 2Department of Complete Denture Prosthodontics, Nihon University School of Dentistry, Yokosuka, Japan; 3Division of Molecular and Regenerative Prosthodontics, Tohoku University Graduate School of Dentistry, Sendai, Miyagi, Japan; 4Department of Prosthodontics and Oral Rehabilitation, 5Yokosuka-Shonan Disaster Health Emergency Research Center and ESR Laboratories, Kanagawa Dental University Graduate School of Dentistry, Yokosuka, Japan Background: Although biomimetic apatite coating is a promising way to provide titanium with osteoconductivity, the efficiency and quality of deposition is often poor. Most titanium implants have microscale surface morphology, and an addition of nanoscale features while preserving the micromorphology may provide further biological benefit. Here, we examined the effect of ultraviolet (UV light treatment of titanium, or photofunctionalization, on the efficacy of biomimetic apatite deposition on titanium and its biological capability.Methods and results: Micro-roughed titanium disks were prepared by acid-etching with sulfuric acid. Micro-roughened disks with or without photofunctionalization (20-minute exposure to UV light were immersed in simulated body fluid (SBF for 1 or 5 days. Photofunctionalized titanium disks were superhydrophilic and did not form surface air bubbles when immersed in SBF, whereas non-photofunctionalized disks were hydrophobic and largely covered with air bubbles during immersion. An apatite-related signal was observed by X-ray diffraction on photofunctionalized titanium after 1 day of SBF immersion, which was equivalent to the one observed after 5 days of immersion of control titanium. Scanning electron microscopy revealed nodular apatite deposition

  20. Multiwalled carbon nanotube reinforced biomimetic bundled gel fibres.

    Science.gov (United States)

    Kim, Young-Jin; Yamamoto, Seiichiro; Takahashi, Haruko; Sasaki, Naruo; Matsunaga, Yukiko T

    2016-08-19

    This work describes the fabrication and characterization of hydroxypropyl cellulose (HPC)-based biomimetic bundled gel fibres. The bundled gel fibres were reinforced with multiwalled carbon nanotubes (MWCNTs). A phase-separated aqueous solution with MWCNT and HPC was transformed into a bundled fibrous structure after being injected into a co-flow microfluidic device and applying the sheath flow. The resulting MWCNT-bundled gel fibres consist of multiple parallel microfibres. The mechanical and electrical properties of MWCNT-bundled gel fibres were improved and their potential for tissue engineering applications as a cell scaffold was demonstrated. PMID:27200527

  1. Acoustic beam control in biomimetic projector via velocity gradient

    Science.gov (United States)

    Gao, Xiaowei; Zhang, Yu; Cao, Wenwu; Dong, Erqian; Song, Zhongchang; Li, Songhai; Tang, Liguo; Zhang, Sai

    2016-07-01

    A biomimetic projector (BioP) based on computerized tomography of pygmy sperm whale's biosonar system has been designed using gradient-index (GRIN) material. The directivity of this BioP device was investigated as function of frequency and the velocity gradient of the GRIN material. A strong beam control over a broad bandwidth at the subwavelength scale has been achieved. Compared with a bare subwavelength source, the main lobe pressure of the BioP is about five times as high and the angular resolution is one order of magnitude better. Our results indicate that this BioP has excellent application potential in miniaturized underwater sonars.

  2. Framing biomimetics in a strategic orientation perspective (biopreneuring)

    DEFF Research Database (Denmark)

    Ulhøi, John Parm

    2015-01-01

    This paper discusses how design originally rooted in biology can be translated into applications outside its original domain (biomimetics), and thus become strategically important for commercial organisations. This paper will also discuss how concepts from organisation and management theory can...... somewhat overlooked. This paper fills some of that void. Business orientation literature is applied to identify some of the key strategic aspects associated with commercial translations. In closing, this paper briefly sketches out some key implications for business research and for affected decision-makers....

  3. 3-D Locomotion control for a biomimetic robot fish

    Institute of Scientific and Technical Information of China (English)

    Zhigang ZHANG; Shuo WANG; Min TAN

    2004-01-01

    This paper concerns with 3-D locomotion control methods for a biomimetic robot fish. The system architecture of the fish is firstly presented based on a physical model of carangiform fish. The robot fish has a flexible body, a rigid caudal fin and a pair of pectoral fins, driven by several servomotors. The motion control of the robot fish are then divided into speed control, orientation control, submerge control and transient motion control, corresponding algorithms are detailed respectively.Finally, experiments and analyses on a 4-1ink, radio-controlled robot fish prototype with 3-D locomotion show its good performance.

  4. Advances in modelling of biomimetic fluid flow at different scales

    Directory of Open Access Journals (Sweden)

    Celata Gian

    2011-01-01

    Full Text Available Abstract The biomimetic flow at different scales has been discussed at length. The need of looking into the biological surfaces and morphologies and both geometrical and physical similarities to imitate the technological products and processes has been emphasized. The complex fluid flow and heat transfer problems, the fluid-interface and the physics involved at multiscale and macro-, meso-, micro- and nano-scales have been discussed. The flow and heat transfer simulation is done by various CFD solvers including Navier-Stokes and energy equations, lattice Boltzmann method and molecular dynamics method. Combined continuum-molecular dynamics method is also reviewed.

  5. Enantioselective Total Synthesis and Structural Revision of (一)-Isochaetominine%(一)-Isochaetominine推测结构的对映选择性全合成与结构修正

    Institute of Scientific and Technical Information of China (English)

    黄培强; 茅中一; 耿辉

    2016-01-01

    报道生物碱isochaetominine推测结构8的对映选择性全合成与结构修正.采用立体多样性合成策略,通过L-色氨酸与L-丙氨酸苄酯组合,以DMDO氧化启动的串联反应为关键反应,经5步高效地完成了isochaetominine推测结构8及其立体异构体(+)-2,3,14-tri-epi-chaetominine (12)的全合成.基于本实验室此前有关毛壳菌素(1)立体多样性合成的工作,天然isochaetominine的结构修正为(一)-11-epi-chaetominine (18).我们此前已完成了该天然产物的首次对映选择性全合成(从L-色氨酸出发,5步,总产率31.6%).此外,通过研究色氨酸与缬氨酸叔丁酯组合,建立了isochaetominine C三个非对映立体异构体的立体多样性合成.最后,证实了化合物13B无法进行C(14)位定点差向异构化,但可以进行C(11)和C(14)双差向异构化.%In this paper,the enantioselective total synthesis and structure revision of the proposed structure of isochaetominine 8 are described.On the basis of the stereodivergent strategy,a highly efficient five-step synthesis of the proposed structure of isochaetominine 8 and its diastereomer (+)-2,3,14-tri-epi-chaetominine (12) was achieved.The method features the use of L-tryptophan and L-alanine benzyl ester as the starting materials,and a dimethyldioxirane (DMDO)-triggered tandem reaction as a key step.A comparison of the physical and spectral data of the natural isochaetominine with those of the diastereomers obtained during our previous stereodivergent synthesis of chaetominine (1),allowed revising the structure of isochaetominine as (一)-11-epi-chaetominine (18).The first enantioselective total synthesis of this natural product has been accomplished previously in our laboratories in five steps,31.6% overall yield from L-tryptophan.Besides,an investigation on the L-tryptophan and L-valine tert-butyl ester-based synthesis of isochaetominine C resulted in a stereodivergent synthesis of three diastereomers of isochaetominine C

  6. Concise Total Synthesis of (±)-Salinosporamide A, (±)-Cinnabaramide A, and Derivatives via a Bis-Cyclization Process: Implications for a Biosynthetic Pathway?

    OpenAIRE

    Ma, Gil; Nguyen, Henry; Romo, Daniel

    2007-01-01

    4-Alkylidene-β-lactones (hetero ketene dimers) and α-amino acids are useful precursors for total syntheses of the β-lactone containing proteasome inhibitors, salinosporamide A, cinnabaramide A, and derivatives. A key step is a nucleophile-promoted, bis-cyclization of keto acids that simultaneously generates the γ-lactam-and β-lactone of these natural products. This reaction sequence may have implications for the biosynthesis of these natural products.

  7. Preparation, anti-biofouling and drag-reduction properties of a biomimetic shark skin surface

    Directory of Open Access Journals (Sweden)

    Xia Pu

    2016-04-01

    Full Text Available Shark skin surfaces show non-smoothness characteristics due to the presence of a riblet structure. In this study, biomimetic shark skin was prepared by using the polydimethylsiloxane (PDMS-embedded elastomeric stamping (PEES method. Scanning electron microscopy (SEM was used to examine the surface microstructure and fine structure of shark skin and biomimetic shark skin. To analyse the hydrophobic mechanism of the shark skin surface microstructure, the effect of biomimetic shark skin surface microstructure on surface wettability was evaluated by recording water contact angle. Additionally, protein adhesion experiments and anti-algae adhesion performance testing experiments were used to investigate and evaluate the anti-biofouling properties of the surface microstructure of biomimetic shark skin. The recorded values of the water contact angle of differently microstructured surfaces revealed that specific microstructures have certain effects on surface wettability. The anti-biofouling properties of the biomimetic shark skin surface with microstructures were superior to a smooth surface using the same polymers as substrates. Moreover, the air layer fixed on the surface of the biomimetic shark skin was found to play a key role in their antibiont adhesion property. An experiment into drag reduction was also conducted. Based on the experimental results, the microstructured surface of the prepared biomimetic shark skin played a significant role in reducing drag. The maximum of drag reduction rate is 12.5%, which is higher than the corresponding maximum drag reduction rate of membrane material with a smooth surface.

  8. Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland-Japp derived 2H-dihydropyran-4-ones: a total synthesis of diospongin B.

    Science.gov (United States)

    Clarke, Paul A; Nasir, Nadiah Mad; Sellars, Philip B; Peter, Alejandra M; Lawson, Connor A; Burroughs, James L

    2016-07-12

    6-Substituted-2H-dihydropyran-4-one products of the Maitland-Japp reaction have been converted into tetrahydropyrans containing uncommon substitution patterns. Treatment of 6-substituted-2H-dihydropyran-4-ones with carbon nucleophiles led to the formation of tetrahydropyran rings with the 2,6-trans-stereochemical arrangement. Reaction of the same 6-substituted-2H-dihydropyran-4-ones with l-Selectride led to the formation of 3,6-disubstituted tetrahydropyran rings, while trapping of the intermediate enolate with carbon electrophiles in turn led to the formation 3,3,6-trisubstituted tetrahydropyran rings. The relative stereochemical configuration of the new substituents was controlled by the stereoelectronic preference for pseudo-axial addition of the nucleophile and trapping of the enolate from the opposite face. Application of these methods led to a synthesis of the potent anti-osteoporotic diarylheptanoid natural product diospongin B. PMID:27340028

  9. Biomimetic strategies for engineering composite tissues.

    Science.gov (United States)

    Lee, Nancy; Robinson, Jennifer; Lu, Helen

    2016-08-01

    The formation of multiple tissue types and their integration into composite tissue units presents a frontier challenge in regenerative engineering. Tissue-tissue synchrony is crucial in providing structural support for internal organs and enabling daily activities. This review highlights the state-of-the-art in composite tissue scaffold design, and explores how biomimicry can be strategically applied to avoid over-engineering the scaffold. Given the complexity of biological tissues, determining the most relevant parameters for recapitulating native structure-function relationships through strategic biomimicry will reduce the burden for clinical translation. It is anticipated that these exciting efforts in composite tissue engineering will enable integrative and functional repair of common soft tissue injuries and lay the foundation for total joint or limb regeneration. PMID:27010653

  10. A biomimetic projector with high subwavelength directivity based on dolphin biosonar

    Science.gov (United States)

    Zhang, Yu; Gao, Xiaowei; Zhang, Sai; Cao, Wenwu; Tang, Liguo; Wang, Ding; Li, Yan

    2014-09-01

    Based on computed tomography of a Yangtze finless porpoise's biosonar system, a biomimetic structure was designed to include air cavity, gradient-index material, and steel outer-structure mimicking air sacs, melon, and skull, respectively. The mainlobe pressure was about three times higher, the angular resolution was one order of magnitude higher, and the effective source size was orders of magnitude larger than those of the subwavelength source without the biomimetic structure. The superior subwavelength directivity over a broad bandwidth suggests potential applications of this biomimetic projector in underwater sonar, medical ultrasonography, and other related applications.

  11. Rapid prototyping of biomimetic vascular phantoms for hyperspectral reflectance imaging

    Science.gov (United States)

    Ghassemi, Pejhman; Wang, Jianting; Melchiorri, Anthony J.; Ramella-Roman, Jessica C.; Mathews, Scott A.; Coburn, James C.; Sorg, Brian S.; Chen, Yu; Joshua Pfefer, T.

    2015-12-01

    The emerging technique of rapid prototyping with three-dimensional (3-D) printers provides a simple yet revolutionary method for fabricating objects with arbitrary geometry. The use of 3-D printing for generating morphologically biomimetic tissue phantoms based on medical images represents a potentially major advance over existing phantom approaches. Toward the goal of image-defined phantoms, we converted a segmented fundus image of the human retina into a matrix format and edited it to achieve a geometry suitable for printing. Phantoms with vessel-simulating channels were then printed using a photoreactive resin providing biologically relevant turbidity, as determined by spectrophotometry. The morphology of printed vessels was validated by x-ray microcomputed tomography. Channels were filled with hemoglobin (Hb) solutions undergoing desaturation, and phantoms were imaged with a near-infrared hyperspectral reflectance imaging system. Additionally, a phantom was printed incorporating two disjoint vascular networks at different depths, each filled with Hb solutions at different saturation levels. Light propagation effects noted during these measurements-including the influence of vessel density and depth on Hb concentration and saturation estimates, and the effect of wavelength on vessel visualization depth-were evaluated. Overall, our findings indicated that 3-D-printed biomimetic phantoms hold significant potential as realistic and practical tools for elucidating light-tissue interactions and characterizing biophotonic system performance.

  12. Formation of Biomimetic Hydroxyapatite Coating on Titanium Plates

    Directory of Open Access Journals (Sweden)

    Ievgen Volodymyrovych PYLYPCHUK

    2014-09-01

    Full Text Available Hydroxyapatite (HA has long been used as a coating material in the implant industry for orthopedic implant applications. HA is the natural inorganic constituent of bone and teeth. By coating titanium (base material of implant engineering because of its lightness and durability with hydroxyapatite, we can provide higher biocompatibility of titanium implants, according to HA ability to form a direct biochemical bond with living tissues. This article reports a biomimetic approach for coating hydroxyapatite with titanium A method of modifying the surface of titanium by organic modifiers (for creating functional groups on the surface, followed by formation "self-assembled" layer of biomimetic hydroxyapatite in simulated body fluid (SBF. FTIR and XPS confirmed the formation of hydroxyapatite coatings on titanium surface. Comparative study of the formation of HA on the surface of titanium plates modified by different functional groups: Ti(≡OH, Ti/(≡Si-OH and Ti/(≡COOH is conducted. It was found that the closest to natural stoichiometric hydroxyapatite Ca/P ratio was obtained on Ti/(≡COOH samples. DOI: http://dx.doi.org/10.5755/j01.ms.20.3.4974

  13. Biomimetic Drag Reduction Study on Herringbone Riblets of Bird Feather

    Institute of Scientific and Technical Information of China (English)

    Huawei Chen; Fugang Rao; Xiaopeng Shang; Deyuan Zhang; Ichiro Hagiwara

    2013-01-01

    Birds have gradually formed various excellent structures such as streamlined shape and hollow shaft of feather to improve their flying performance by millions of years of natural selection.As typical property of bird feather,herringbone riblets align along the shaft of each feather,which is caused by perfect link of barbs,especially for the primary and secondary feathers of wings.Such herringbone riblets of feather are assumed to have great impact on drag reduction.In this paper,microstructures of secondary feathers of adult pigeons are investigated by SEM,and their structural parameters are statistically obtained.Based on quantitative analysis of feather structure,novel biomimetic herringbone riblets with narrow smooth edge are proposed to reduce surface drag.In comparison with traditional microgroove riblets and other drag reduction structures,the drag reduction rate of the proposed biomimetic herringbone riblets is experimentally clarified up to 16%,much higher than others.Moreover,the drag reduction mechanism of herringbone riblets are also confirmed and exploited by CFD.

  14. Helicoidal microstructure of Scarabaei cuticle and biomimetic research

    Energy Technology Data Exchange (ETDEWEB)

    Chen, B. [Department of Engineering Mechanics, Chongqing University, Chongqing 400044 (China)]. E-mail: bchen@cqu.edu.cn; Peng, X. [Department of Engineering Mechanics, Chongqing University, Chongqing 400044 (China); Cai, C. [Department of Applied Physics, Chongqing University, Chongqing 400044 (China); Niu, H. [Department of Engineering Mechanics, Chongqing University, Chongqing 400044 (China); Wu, X. [Department of Engineering Mechanics, Chongqing University, Chongqing 400044 (China)

    2006-05-15

    Insect cuticles as a natural biocomposite include many favorable microstructures which have been refined over centuries and endow the cuticles excellent mechanical and physical properties, such as light weight, high strength and toughness, etc. The various microstructures of a Scarabaei cuticle are investigated with a scanning electronic microscope and reported in this paper. It is found that the cuticle is a kind of fiber-reinforced biocomposite composed of chitin-fiber layers and sclerous protein matrixes. Different chitin-fiber layers have different orientations, composed of crossed and helicoidal structures at different location. In the helicoidal structure, each fiber layer rotates with an almost fixed angle against its neighboring layer. The maximum pullout energy of the helicoidal structure is analyzed based on the representative model of the structure. The result shows that the pullout energy of the helicoidal structure is markedly larger than that of the conventional 0{sup o}-structure. A biomimetic composite with the observed helicoidal structure is designed and fabricated. A comparative test shows that the fracture toughness of the biomimetic composite is markedly larger than that of the 0{sup o}-layer composite.

  15. Small-Scale Fabrication of Biomimetic Structures for Periodontal Regeneration

    Directory of Open Access Journals (Sweden)

    David William Green

    2016-02-01

    Full Text Available The periodontium is the supporting tissues for the tooth organ and is vulnerable to destruction, arising from overpopulating pathogenic bacteria and spirochaetes. The presence of microbes together with host responses can destroy large parts of the periodontium sometimes leading tooth loss. Permanent tissue replacements are made possible with tissue engineering techniques. However, existing periodontal biomaterials cannot promote proper tissue architectures, necessary tissue volumes within the periodontal pocket and a water-tight barrier, to become clinically acceptable. New kinds of small-scale engineered biomaterials, with increasing biological complexity are needed to guide proper biomimetic regeneration of periodontal tissues. So the ability to make compound structures with small modules, filled with tissue components, is a promising design strategy for simulating the anatomical complexity of the periodotium attachement complexes along the tooth root and the abutment with the tooth collar. Anatomical structures such as, intima, adventitia and special compartments such as the epithelial cell rests of Malassez or a stellate reticulum niche need to be engineered from the start of regeneration to produce proper periodontium replacement.. It is our contention that the positioning of tissue components at the origin is also necessary to promote self-organising cell-cell connections, cell-matrix connections. This leads to accelerated, synchronized and well-formed tissue architectures and anatomies. This strategy is a highly effective preparation for tackling periodontitis, periodontium tissue resorption and to ultimately prevent tooth loss. Furthermore, such biomimetic tissue replacements will tackle problems associated with dental implant support and perimimplantitis.

  16. Biomimetics inspired surfaces for drag reduction and oleophobicity/philicity

    Directory of Open Access Journals (Sweden)

    Bharat Bhushan

    2011-02-01

    Full Text Available The emerging field of biomimetics allows one to mimic biology or nature to develop nanomaterials, nanodevices, and processes which provide desirable properties. Hierarchical structures with dimensions of features ranging from the macroscale to the nanoscale are extremely common in nature and possess properties of interest. There are a large number of objects including bacteria, plants, land and aquatic animals, and seashells with properties of commercial interest. Certain plant leaves, such as lotus (Nelumbo nucifera leaves, are known to be superhydrophobic and self-cleaning due to the hierarchical surface roughness and presence of a wax layer. In addition to a self-cleaning effect, these surfaces with a high contact angle and low contact angle hysteresis also exhibit low adhesion and drag reduction for fluid flow. An aquatic animal, such as a shark, is another model from nature for the reduction of drag in fluid flow. The artificial surfaces inspired from the shark skin and lotus leaf have been created, and in this article the influence of structure on drag reduction efficiency is reviewed. Biomimetic-inspired oleophobic surfaces can be used to prevent contamination of the underwater parts of ships by biological and organic contaminants, including oil. The article also reviews the wetting behavior of oil droplets on various superoleophobic surfaces created in the lab.

  17. Biomimetic surface modification of polyurethane with phospholipids grafted carbon nanotubes.

    Science.gov (United States)

    Tan, Dongsheng; Liu, Liuxu; Li, Zhen; Fu, Qiang

    2015-08-01

    To improve blood compatibility of polyurethane (PU), phospholipids grafted carbon nanotubes (CNTs) were prepared through zwitterion-mediated cycloaddition reaction and amide condensation, and then were added to the PU as fillers via solution mixing to form biomimetic surface. The properties of phospholipids grafted CNTs (CNT-PC) were investigated by thermal gravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS) and proton nuclear magnetic resonance ((1) H NMR). The results indicated that the phospholipids were grafted onto CNTs in high efficiency, and the hydrophilicity and dispersibility of the modified CNTs were improved effectively. The structures and properties of composites containing CNT-PC were investigated by optical microscope, XPS, and water contact angles. The results indicated that phospholipids were enriched on the surface with addition of 0.1 wt % of CNT-PC, which significantly reduced protein adsorption and platelet adhesion. The method of carrying phospholipids on the nanofiller to modify polymers has provided a promising way of constructing biomimetic phospholipid membrane on the surface to improve blood compatibility. PMID:25630300

  18. Biomimetics of fetal alveolar flow phenomena using microfluidics.

    Science.gov (United States)

    Tenenbaum-Katan, Janna; Fishler, Rami; Rothen-Rutishauser, Barbara; Sznitman, Josué

    2015-01-01

    At the onset of life in utero, the respiratory system begins as a liquid-filled tubular organ and undergoes significant morphological changes during fetal development towards establishing a respiratory organ optimized for gas exchange. As airspace morphology evolves, respiratory alveolar flows have been hypothesized to exhibit evolving flow patterns. In the present study, we have investigated flow topologies during increasing phases of embryonic life within an anatomically inspired microfluidic device, reproducing real-scale features of fetal airways representative of three distinct phases of in utero gestation. Micro-particle image velocimetry measurements, supported by computational fluid dynamics simulations, reveal distinct respiratory alveolar flow patterns throughout different stages of fetal life. While attached, streamlined flows characterize the shallow structures of premature alveoli indicative of the onset of saccular stage, separated recirculating vortex flows become the signature of developed and extruded alveoli characteristic of the advanced stages of fetal development. To further mimic physiological aspects of the cellular environment of developing airways, our biomimetic devices integrate an alveolar epithelium using the A549 cell line, recreating a confluent monolayer that produces pulmonary surfactant. Overall, our in vitro biomimetic fetal airways model delivers a robust and reliable platform combining key features of alveolar morphology, flow patterns, and physiological aspects of fetal lungs developing in utero. PMID:25759753

  19. Conversion of methane to higher hydrocarbons (Biomimetic catalysis of the conversion of methane to methanol). Final report

    Energy Technology Data Exchange (ETDEWEB)

    Watkins, B.E.; Taylor, R.T.; Satcher, J.H. [and others

    1993-09-01

    In addition to inorganic catalysts that react with methane, it is well-known that a select group of aerobic soil/water bacteria called methanotrophs can efficiently and selectively utilize methane as the sole source of their energy and carbon for cellular growth. The first reaction in this metabolic pathway is catalyzed by the enzyme methane monooxygenase (MMO) forming methanol. Methanol is a technology important product from this partial oxidation of methane since it can be easily converted to liquid hydrocarbon transportation fuels (gasoline), used directly as a liquid fuel or fuel additive itself, or serve as a feedstock for chemicals production. This naturally occurring biocatalyst (MMO) is accomplishing a technologically important transformation (methane directly to methanol) for which there is currently no analogous chemical (non-biological) process. The authors approach has been to use the biocatalyst, MMO, as the initial focus in the development of discrete chemical catalysts (biomimetic complexes) for methane conversion. The advantage of this approach is that it exploits a biocatalytic system already performing a desired transformation of methane. In addition, this approach generated needed new experimental information on catalyst structure and function in order to develop new catalysts rationally and systematically. The first task is a comparative mechanistic, biochemical, and spectroscopic investigation of MMO enzyme systems. This work was directed at developing a description of the structure and function of the catalytically active sites in sufficient detail to generate a biomimetic material. The second task involves the synthesis, characterization, and chemical reactions of discrete complexes that mimic the enzymatic active site. These complexes were synthesized based on their best current understanding of the MMO active site structure.

  20. Effect of Different Light Intensities on Total Phenolics and Flavonoids Synthesis and Anti-oxidant Activities in Young Ginger Varieties (Zingiber officinale Roscoe

    Directory of Open Access Journals (Sweden)

    Ali Ghasemzadeh

    2010-10-01

    Full Text Available Nowadays, phytochemicals and antioxidants in plants are raising interest in consumers for their roles in the maintenance of human health. Phenolics and flavonoids are known for their health-promoting properties due to protective effects against cardiovascular disease, cancers and other disease. Ginger (Zingiber officinale is one of the traditional folk medicinal plants and it is widely used in cooking in Malaysia. In this study, four levels of glasshouse light intensities (310, 460, 630 and 790 μmol m−2s−1 were used in order to consider the effect of light intensity on the production, accumulation and partitioning of total phenolics (TP, total flavonoids (TF and antioxidant activities in two varieties of Malaysian young ginger (Zingiber officinale. TF biosynthesis was highest in the Halia Bara variety under 310 μmol m−2s−1 and TP was high in this variety under a light intensity of 790 μmol m−2s−1. The highest amount of these components accumulated in the leaves and after that in the rhizomes. Also, antioxidant activities determined by the 1,1-Diphenyl-2-picryl-hydrazyl (DPPH assay in both of varieties, increased significantly (p ≤ 0.01 with increasing TF concentration, and high antioxidant activity was observed in the leaves of Halia Bara grown under 310 μmol m−2s−1. The ferric reducing (FRAP activity of the rhizomes was higher than that of the leaves in 310 μmol m−2s−1 of sun light. This study indicates the ability of different light intensities to enhance the medicinal components and antioxidant activities of the leaves and young rhizomes of Zingiber officinale varieties. Additionally, this study also validated their medicinal potential based on TF and TP contents.