CAS: 2133-34-8; (S)-Azetidine-2-Carboxylic Acid

该化合物是一种非蛋白性氨基酸,由四人组成,由四人组成的Azetidine环组成,具有独特的相容限制,其立体特性(S)配置使其在peptide合成和药用化学中具有价值,它作为硬骨架,可以调节peptide脊柱灵活性,提高代谢稳定性.该化合物在酶抑制剂和生物活性peptides的设计中特别有用,因为它能够影响二级结构.其高纯度和定义明确的立体化学确保研究应用中的再生性.此外,它与标准的固相能阶段peptide合成协议的兼容性使得能够有效地融入复杂的分子结构.

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相似化合物

2517-04-6 7729-30-8 136552-06-2

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合成工艺路线路线简述

    📜S-腺苷蛋氨酸置于c-His6-Tagged Azej From Escherichia Coli体系中,用 Aq. Buffer 用作溶剂,化学反应 4.0H,反应生成(S)-(-)-2-羧基环丁胺
    参考文献:铜绿假单胞菌中群体感应调节非核糖体肽合成酶途径产生的含氮杂环丁烷的生物碱.
    标题:铜绿假单胞菌中群体感应调节非核糖体肽合成酶途径产生的含氮杂环丁烷的生物碱.
    摘要:铜绿假单胞菌显示出令人印象深刻的代谢多功能性,从而确保其在各种环境中的生存.本文报道的是鉴定自铜绿假单胞菌pao1的罕见的含氮杂环丁烷的生物碱,称为氮杂环丁烷酰胺,其衍生自保守的,群体感应调节的非核糖体肽合成酶(nrps)途径.氮杂环丁烷基序的生物合成已通过基因灭活,进食实验和体外生化表征得以阐明,其中涉及一种新的s-腺苷甲硫氨酸依赖性酶,以生成氮杂环丁烷2-羧酸,这是nrps的一个不常见的组成部分.铜绿假单胞菌的突变体不能产生azetidomonamides具有生长优势在体外高细胞密度和在显示快速毒力大蜡螟模型,推断azetidomonamides的功能作用在宿主适应.这项工作为研究氮杂环磷酰胺和相关化合物在致病性和环境细菌中的生物学功能开辟了道路.
    Doi:10.1002/anie.201809981

    海关参考信息

    专利信息


    专利号:US-12240808-B2
    优先权日:2021-05-28
    标 题 :Process for the synthesis of calebin-a and its intermediates
    发明人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; MUTHUKAMAN NAGARAJAN; NAIDU PENTAKOTA PARADESI
    权利人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; MUTHUKAMAN NAGARAJAN; NAIDU PENTAKOTA PARADESI
    摘要:The invention discloses novel intermediates in the synthesis of Calebin A represented by formula 3. The invention also covers processes for the synthesis of Calebin-A and its analogs using compounds of formula 3.

    专利号:US-6376649-B1
    优先权日:1998-12-18
    标题 :Methods for the synthesis of α- hydroxy-β-amino acid and amide derivatives
    发明人:SEMPLE JOSEPH E; LEVY ODILE E
    权利人:CORVAS INT INC
    摘要:Methods for the synthesis of alpha-hydroxy-beta-amino acid and amide derivatives and alpha-ketoamide derivatives and novel derivatives made by these methods are provided. These methods involve reacting a N-terminally blocked (protected) aminoaldehyde with an isonitrile and a carboxylic acid to give an amino-alpha-acyloxy carboxamide. The acyloxy group may be removed to give the derivative. Alternatively the protecting group is removed and acyl shift occurs to give the derivative. These derivatives are useful in the synthesis of compounds such as peptidyl alpha-ketoamides and alpha-hydroxy-beta-carboxylic acid and amide derivatives. Certain of these compounds have been reported to have activity as inhibitors of proteases, such as serine proteases and cysteine proteases.

    专利号:US-4190579-A
    优先权日:1977-12-29
    标题:Synthesis of beta-lactams from azetidine carboxylic acid esters
    发明人:LIPSHUTZ BRUCE H; WASSERMAN HARRY H; WU JAMES S
    权利人:RESEARCH CORP
    摘要:Azetidine carboxylic acid esters are converted into enol silyl ethers which, as enamino ketene acetals, undergo ready oxidative cleavage of the ethylenically unsaturated double bond, e.g. by dye-sensitized photo-oxygenation, to form beta-lactams. The beta-lactams and substitution products thereof are useful intermediates in the synthesis of biologically active lactams.

    专利号:US-4110380-A
    优先权日:1974-05-06
    标题 :Asymmetric synthesis of organic compounds
    发明人:HAJOS ZOLTAN GEORGE; PARRISH DAVID RICHARD
    权利人:HOFFMANN LA ROCHE
    摘要:Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a 'meso' type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.

    专利号:US-9206222-B2
    优先权日:2009-06-29
    标题:Solid phase peptide synthesis of peptide alcohols
    发明人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN
    权利人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN; CENTRE NAT RECH SCIENT
    摘要:The present invention relates to the synthesis of depsipeptides on solid phase support. Said depsipeptides are then implicated in a solution phase O—N acyl shift enabling to obtain the corresponding peptide alcohols.

    专利号:US-2003180804-A1
    优先权日:2001-10-29
    标题:Solid phase synthesis of chemical libraries
    发明人:PRYOR KENT E; LEWIS RONALD D; BROWN JASON W
    权利人:CORVAS INT INC
    摘要:The present invention provides compounds and compound libraries that are useful as protease modulators. The compounds and compound libraries are preferably made using the methods of the present invention which utilize peptide synthesis and combinatorial chemistry methods on a solid phase.

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Sato T, Hoshida H, Akada R. Inhibition of Distinct Proline- or N-Acetylglucosamine-Induced Hyphal Formation Pathways by Proline Analogs in Candida albicans. Biomed Res Int. 2020 Nov 17;2020:7245782. doi: 10.1155/2020/7245782.
    2: Berg MD, Zhu Y, Isaacson J, Genereaux J, Loll-Krippleber R, Brown GW, Brandl CJ. Chemical-Genetic Interactions with the Proline Analog L-Azetidine-2-Carboxylic Acid in Saccharomyces cerevisiae. G3 (Bethesda). 2020 Dec 3;10(12):4335-4345. doi: 10.1534/g3.120.401876.
    3: Mat Nanyan NSB, Watanabe D, Sugimoto Y, Takagi H. Involvement of the stress- responsive transcription factor gene MSN2 in the control of amino acid uptake in Saccharomyces cerevisiae. FEMS Yeast Res. 2019 Aug 1;19(5):foz052. doi: 10.1093/femsyr/foz052. 51(8):1221-1232. doi: 10.1007/s00726-019-02763-w. Epub 2019 Jul 13. 7(12):239. doi: 10.3390/cells7120239.

    合成参考文献


    摘要:COUSE NL ET AL; STRUCTURAL ABERRATION IN T-EVEN BACTERIOPHAGE. I. SPECIFICITY OF INDUCTION OF ABERRATIONS; VIROLOGY 42(3) 590 (1970)
    摘要:KERSHENOBICH D, ROJKIND M; EFFECT OF THE ADMINISTRATION OF L-AZETIDINE-2-CARBOXYLIC ACID ON ALBUMIN AND TRANSFERRIN BIOSYNTHESIS BY LIVER SLICES OF RATS TREATED WITH CARBON TETRACHLORIDE; BIOCHIM BIOPHYS ACTA 319(2) 216 (1973)
    摘要:RUCH JV, KARCHER-DJURICIC V; TOOTH MORPHOGENESIS AND CYTODIFFERENTIATIONS IN VITRO. EFFECT OF 2-L-AZETIDINECARBOXYLIC ACID; COLLOQ INST NATL SANTE RECH MED 19(OTES CULT) 109 (1973)
    摘要:Shepard, T. H. Catalog of Teratogenic Agents. 3rd ed. Baltimore, MD.: Johns Hopkins University Press, 1980., p. 31
    参考文献:10.1042/bj0700626
    摘要:FOWDEN L, BRYANT M. Nitrogenous compounds and nitrogen metabolism in the Liliaceae. 4. Isolation of azetidine-2-carboxylic acid and evidence for the occurence of alpha gamma-diaminobutyric acid in Polygonatum. Biochem J. 1958 Dec;70(4):626–9.
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