CAS: 70982-53-5; L-Vinylglycine

该化合物是一种手性非蛋白性氨基酸,在β位置上有一个维尼基类,使其成为有机合成和制药应用中的宝贵基石.它的对应(S)配置在非对称合成和生物活性化合物的制作方面特别有用.该维尼基类提供多种反应,通过交叉组合,循环添加或聚合反应使功能化.该化合物通常用于浸泡剂改造,并作为异环菌类的先质.其高纯度和定义明确的立体化学确保研究和工业过程的再生性.它适合于医药化学和材料科学,为开发新型治疗和功能性材料提供了一个强有力的平台.

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合成工艺路线路线简述

    N-Acetyl-2-Aminobut-3-Enoic Acid 反应 2.0H,反应生成 L-乙烯基甘氨酸
    参考文献:Syntheses Of Optically Active,Protected And Unprotected Vinylglycines.
    标题:Syntheses Of Optically Active,Protected And Unprotected Vinylglycines.
    摘要:乙烯基甘氨酸(2)在酸性条件下会发生消旋化.通过酶水解 N-乙酰乙烯基甘氨酸 (5),然后重结晶,从 2-Hcl 中得到了光学纯度为 2 的乙烯基甘氨酸.(在酸性条件下,(S)-N-(甲氧羰基)乙烯基甘氨酸(6)的构型非常不稳定,因此无法从 2 中得到光学纯的 6.另一方面,从(S)-高丝氨酸合成了构型稳定的(S)-N-(9-苯基芴-9-基)乙烯基甘氨酸甲酯(9).
    DOI:10.1248/cpb.42.1927

    海关参考信息

    专利信息


    专利号:WO-9726002-A1
    优先权日:1996-01-17
    标 题:Synthesis of conformationally restricted amino acids, peptides and peptidomimetics by catalytic ring closing metathesis
    发明人:GRUBBS ROBERT H; MILLER J SCOTT; BLACKWELL HELEN E
    权利人:CALIFORNIA INST OF TECHN
    摘要:A method for synthesizing conformationally restricted amino acids, peptides, and peptidomimetics by ring closing metathesis. The method includes the steps of synthesizing a peptide precursor containing first and second unsaturated C-C bonds and contacting the peptide precursor with an RCM catalyst to yield a conformationally restricted peptide. Suitable peptide precursors may contain two or more unsaturated C-C bonds. These bonds may be olefinic bonds and may be contained in first and second alkenyl groups which may be allyl groups. The RCM catalyst may be a Ruthenium or Osmium carbene complex catalyst and more specifically, a Ruthenium or Osmium carbene complex catalyst that includes a Ruthenium or Osmium metal center that is in a +2 oxidation state, has an electron count of 16, and is pentacoordinated. The method may be carried out using solid-phase-peptide-synthesis techniques. In this embodiment, the precursor, which is anchored to a solid support, is contacted with an RCM catalyst and the product is then cleaved from the solid support to yield a conformationally restricted peptide.

    专利号:US-2024209029-A1
    优先权日:2021-04-21
    标题:Adiponectin glycopeptides and compositions and methods of use thereof
    发明人:WANG YU; LI XUECHEN; XU AIMIN; WU HONGXIANG; ZHANG YIWEI; LI YUANXIN
    权利人:UNIV HONG KONG
    摘要:An improved method for the chemical synthesis of glycosylated peptides has been developed. The method uses stereoselective glycan synthesis and chemical peptide ligation to produce glycopeptides at lower-cost and with higher efficiency/yield compared to conventional methods. In particular, a method for the large-scale, chemical synthesis of hydroxylated amino acid building blocks and glycosylated amino acids suitable for solid phase peptide synthesis (SPPS) are disclosed. SPPS-based methods using the glycosylated amino acids to chemically synthesize adiponectin-like peptides are also described. In vivo studies show that the adiponectin mimicking glycopeptides exhibit significant anticancer, anti-obesity and insulin sensitizing effects. Pharmaceutical compositions of the synthetic glycopeptides and methods of use thereof in treating diseases associated with deficient adiponectin are also described.

    专利号:WO-2008098280-A1
    优先权日:2007-02-16
    标题:Methods for the synthesis of dicarba bridges in growth hormone peptides
    发明人:ROBINSON ANDREA JANE; VAN LIEROP BIANCA; WHELAN AMANDA
    权利人:POLYCHIP PHARMACEUTICALS PTY; UNIV MONASH; ROBINSON ANDREA JANE; VAN LIEROP BIANCA; WHELAN AMANDA
    摘要:The invention relates to peptides comprising the carboxy terminal sequence of a growth hormone or an analogue of such a peptide in which the disulfide bridge is replaced by a dicarba bridge. Compositions containing such dicarba bridged peptides and method of treating obesity in an animal such as a human comprising administration of such dicarba bridged peptides are also disclosed.

    专利号:US-6069272-A
    优先权日:1992-03-09
    标 题:Simplified method for the production of vinyl glycine (2-aminobut-3-enoic acid) and a convenient resolution of a derivative
    发明人:CROUT DAVID HERBERT GEORGE; HALLINAN KEITH OLIVER
    权利人:HOECHST AG
    摘要:The invention relates to a three-step synthesis of vinyl glycine (1) using a cheap, commercially available starting material (3-butenenitrile (2)) and using cheap, simple reagents. Also disclosed is a convenient optical resolution of the N-tert.butyloxycarbonyl derivative by papain-catalyzed enantioselective esterification in a two-phase system.

    专利号:US-8580998-B2
    优先权日:2008-12-11
    标题 :Preparation of alkenes by mild thermolysis of sulfoxides
    发明人:LONG TIMOTHY EDWARD; PATEL SRAVAN KUMAR
    权利人:LONG TIMOTHY EDWARD; PATEL SRAVAN KUMAR; UNIV GEORGIA
    摘要:Embodiments of this disclosure, among others, encompass methods for generating alkenes under mild thermolytic conditions that can provide almost total conversion of a precursor compound to an alkene without isomerization or the need to chromatographically purify the final product By selectively blocking the amino and carboxy groups of the derivatized amino acid, the methods of the disclosure provide for the synthesis of a peptide having the vinylglycine moiety at either the carboxy or the amino terminus of the peptide The mild conditions for the thermolytic removal of an o-NO 2 -phenyl substituted aryl group ensure that there is minimal if any damage to thermally sensitive conjugates such as a peptide bearing the vinylglycine The methods of the present disclosure have practical applications for the preparation of unsaturated compounds under mild, thermolytic conditions.

    专利号:US-7393954-B2
    优先权日:2002-12-12
    标题:Process for the production of pentostatin aglycone and pentostatin
    发明人:NADJI SOURENA; SMOOT JAMES; SAMPATH UMASHANKER
    权利人:RELIABLE BIOPHARMACEUTICAL COR
    摘要:A novel, scaleable and improved process for preparing pentostatin and its analogs is disclosed. The method comprises the diastereospecific synthesis of the nucleobase from commercially available L-Dialkyl tartarates.
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    主要参考文献

    参考标题:Synthesis Of 2'-Epi-Distichonic Acid A, An Iron-Chelating Amino Acid Derivative.
    作者:Takashi Tashiro,Shinji Fushiya,Shigeo Nozoe
    摘要:2'-Epi-Distichonic Acid A (4B), An Iron-Chelating Amino Acid Derivative Was Synthesized Starting From L-Vinylglycine Epoxide (6B). Reaction Of 6B With Glycine Ester 17 Afforded A β-Hydroxy Amino Acid Derivative (18). Reductive Coupling Of 21 Derived From 18 With L-Malic-β-Semialdehyde (25) Gave 2'-Epi-Distichonic Acid A (4B) After Deprotection.

    合成参考文献


    摘要:Hollmann, F., Science of Synthesis Knowledge Updates, (2021) 3, 437.
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