N-acetyl-L-phenylalanine vinyl ester | 147092-06-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-L-phenylalanine vinyl ester
• 英文别名: vinyl N-acetyl-L-phenylalaninate；(L)-N-acetyl-phenylalanine vinyl ester；N-acetylphenylalanine vinyl ester；ethenyl (2S)-2-acetamido-3-phenylpropanoate
• CAS: 147092-06-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: KTCGQRCQNDVTDC-LBPRGKRZSA-N

物化性质

• 沸点：
  424.1±45.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-1-戊醇 、 N-acetyl-L-phenylalanine vinyl ester 在 KCl-Subtilisin Bacillus lentus 作用下， 以 叔丁醇 为溶剂， 反应 120.0h， 生成 (S)-2-Acetylamino-3-phenyl-propionic acid 2-methyl-pentyl ester
  参考文献：
  名称：

  Probing the specificity of the S 1 ′, leaving group, site of subtilisin Bacillus lentus using an enzyme-catalyzed transesterification reaction

  摘要：

  Subtilisin Bacillus lentus catalyzes transesterifications between N-acetyl-L-phenylalanine vinyl ester and a wide range of alcohols. Reaction yields are high when primary alcohols are used, and quantitative with methanol. With chiral alcohols, the reaction is enantioselective, and the stereoselectivity is reversed on going from open chain secondary alcohols to beta-branched primary alcohols. A model is proposed to account for this change in absolute configuration preference. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00022-6
• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 在 4-二甲氨基吡啶 、 双氧水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 N-acetyl-L-phenylalanine vinyl ester
  参考文献：
  名称：

  A New Methodology for the Preparation of Vinyl Esters

  摘要：

  新方法已研发成功，用于制备未取代的烯醇酯。通过获得乙烯基芳香α-氨基酸酯，展示了其应用。简要调查制备其他疏水性乙烯酯也取得成功。由于采用温和反应条件，相信这一途径可通向其他烯醇酯。

  DOI：

  10.1055/s-1993-25802

文献信息

• Regio‐ and Stereoselective Chan‐Lam‐Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
  作者：Luuk Steemers、Linda Wijsman、Jan H. van Maarseveen

  DOI：10.1002/adsc.201800914

  日期：2018.11.5

  Efficient and scalable Cu(II)‐mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2‐substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N‐hydroxyimides

  提出了一种高效，可扩展的Cu（II）介导的烯基环硼氧烷和硼酸羧酸的烯醇酯化方法。该反应在脂肪族和芳香族羧酸与几种烯基环硼氧烷化合物的组合中显示出广泛的范围。对于2取代的烯基硼氧烷，双键构型完全保留在烯醇酯产品中。N-羟基酰亚胺和酰亚胺也可以在相应的酰氧基乙烯基烯醇醚和乙烯基酰胺中转化。最后，除甲硫氨酸外，所有其他19种规范氨基酸都显示出它们的相容性，从而以立体选择性方式生成烯醇酯。
• Ready protease-catalyzed synthesis of carbohydrate–amino acid conjugates
  作者：Viviane Boyer、Benjamin G. Davis、Mincho Stanchev、Antony J. Fairbanks

  DOI：10.1039/b104137c

  日期：——

  The protease-catalyzed synthesis of amino acid ester–carbohydrate conjugates as glycopeptide analogues has been achieved in a highly regioselective and carbohydrate-specific manner using amino acid vinyl ester acyl donors and minimally or completely unprotected carbohydrate acyl acceptors, which together probed active sites of proteases to reveal yield efficiencies that are modulated by the carbohydrate C-2 substituent, and that may be exploited to allow selective one-pot syntheses.

  利用氨基酸乙烯酯酰基供体和最小程度或完全无保护的碳水化合物酰基受体，通过蛋白酶催化的氨基酸酯-碳水化合物偶联反应，实现了作为糖肽类似物的氨基酸酯-碳水化合物偶联物的高区域选择性和碳水化合物特异性合成。这些偶联物共同探测了蛋白酶的活性位点，揭示了由碳水化合物C-2取代基调节的产率效率，并可能被利用以实现选择性的单锅合成。
• COMPOSITION THAT CAN BE CURED BY POLYMERISATION FOR THE PRODUCTION OF BIODEGRADABLE, BIOCOMPATIBLE, CROSS-LINKABLE POLYMERS ON THE BASIS OF POLYVINYL ALCOHOL
  申请人：Liska Robert

  公开号：US20100303804A1

  公开（公告）日：2010-12-02

  The present invention relates to a polymerization-curable composition for the preparation of biodegradable, biocompatible, cross-linked polymers on the basis of polyvinyl alcohol comprising: 5 to 100% by weight of (a) vinyl ester monomer(s) of one of the general formulas (I) to (III): wherein X is oxygen, sulfur, nitrogen, or phosphorus; n is 1 to 1000, at least 20% of the n being ≧2; the R 1 are selected from hydrogen; straight, branched or cyclic, saturated or unsaturated, n-valent hydrocarbon groups having 1 to 30 carbon atoms, which optionally have heteroatoms and are optionally substituted with one or more substituents selected from —OH, —COON, —CN, —CHO, and ═O, and n-valent radicals of biodegradable, biocompatible oligomers and polymers; m is an integer from 1 to 5; the R 2 are selected from hydrogen, —OH, ═O, and the options listed for R 1 ; and the R 3 are selected from hydrogen, —OH, and the options listed for R 1 ; 0 to 50% by weight of ethylenically unsaturated co-monomers; 0 to 10% by weight of (a) polymerization initiator(s); and 0 to 95% by weight of solvent(s).

  本发明涉及一种用于制备基于聚乙烯醇的可生物降解、生物相容、交联聚合物的聚合固化组合物，包括：按重量计5至100%的(a)乙烯酸酯单体，其具有下列通式(I)至(III)之一： 其中X为氧、硫、氮或磷；n为1至1000，n的至少20%为≧2；R 1 选自氢；直链、支链或环状、饱和或不饱和、含有1至30个碳原子的n价碳氢基团，该基团可选地具有杂原子，并可选地被选自—OH、—COON、—CN、—CHO和═O的一个或多个取代基以及生物降解、生物相容寡聚物和聚合物的n价基团取代；m为1至5的整数；R 2 选自氢、—OH、═O以及R 1 中列出的选项；R 3 选自氢、—OH以及R 1 中列出的选项；按重量计0至50%的乙烯基不饱和共聚单体；按重量计0至10%的(a)聚合引发剂；按重量计0至95%的溶剂。
• Chemically modified mutant serine hydrolases show improved catalytic activity and chiral selectivity
  申请人：Jones Bryan John

  公开号：US20050282248A1

  公开（公告）日：2005-12-22

  This invention provides novel chemically modified mutant serine hydrolases that catalyze a transamidation and/or a transpeptidation and/or a transesterification reaction. The modified serine hydrolases have one or more amino acid residues in a subsite replaced with a cysteine, wherein the cysteine is modified by replacing the thiol hydrogen in the cysteine with a substituent group providing a thiol side chain comprising a moiety selected from the group consisting of a polar aromatic substituent, an alkyl amino group with a positive charge, and a glycoside. In particularly preferred embodiments, the substitutents include an oxazolidinone, a C 1 to C 15 alkyl amino group with a positive charge, or a glycoside.

  该发明提供了一种新型的化学修饰突变丝氨酸水解酶，其催化转酰胺化和/或转肽化和/或酯交换反应。改性的丝氨酸水解酶具有一个或多个氨基酸残基在一个亚位点上被取代为半胱氨酸，其中半胱氨酸通过用提供来自一组成员的基团的硫醇侧链替换半胱氨酸中的硫氢原子而进行修饰，所述基团包括极性芳香基团、带有正电荷的烷基氨基团和糖苷。在特别优选的实施方式中，取代基包括噁唑啉酮、具有正电荷的C1到C15烷基氨基团或糖苷。
• Method for preparing ester linked peptide-carbohydrate conjugates
  申请人：——

  公开号：US20040208883A1

  公开（公告）日：2004-10-21

  A method of producing an ester linked carbohydrate-peptide conjugate is provided comprising: (a) providing a vinyl ester amino acid group, and (b) reacting the vinyl ester amino acid with a carbohydrate acyl acceptor in the presence of an enzyme, to produce thereby an ester-linked carbohydrate-peptide conjugate. Also provided are ester linked carbohydrate-peptide conjugates obtainable by such methods.

  提供了一种生产酯化的碳水化合物-肽共轭物的方法，包括：(a)提供一种乙烯基酯氨基酸基团，以及(b)在酶的存在下，将乙烯基酯氨基酸与碳水化合物酰基受体反应，从而产生酯化的碳水化合物-肽共轭物。还提供了通过这种方法获得的酯化的碳水化合物-肽共轭物。