2-benzyl-3-methylthiopropanoic acid methyl ester | 666197-94-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-benzyl-3-methylthiopropanoic acid methyl ester
• 英文别名: Methyl 2-benzyl-3-methylsulfanylpropanoate；methyl 2-benzyl-3-methylsulfanylpropanoate
• CAS: 666197-94-0
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: HSYKBWKOMPJGKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-3-methylthiopropanoic acid methyl ester 在 sodium hydroxide 、 氯化亚砜 、 phosphate buffer 、 α-chymotrypsin 作用下， 以 水 为溶剂， 反应 11.0h， 生成 (S)-2-benzyl-3-methylthiopropanoic acid methyl ester
  参考文献：
  名称：

  Optically active 2-benzyl-3-methanesulfinylpropanoic acid: Synthesis and evaluation as inhibitors for carboxypeptidase A

  摘要：

  All four possible stereomers of 2-benzyl-3-methanesulfinylpropanoic acid were synthesized and evaluated as inhibitors for carboxypeptidase A to find that the isomer having the (2S,4S)-configuration is most potent followed by isomers of (2R,4S)- and (2S,4R)-configurations. The stereochemical preferences shown by the isomers of the inhibitor in binding to the enzyme suggest that the sulfoxide oxygen in the inhibitor fails to ligate the active site zinc ion but may form a hydrogen bond with the guanidinium moiety of Arg-127 like the carbonyl oxygen of scissile peptide bond of oligopeptide Substrate of the enzyme does. It may thus be inferred that a sulfoxide moiety may serve as an isosterer of a carboxamide moiety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00481-4
• 作为产物：
  描述：

  甲醇 、 (+/-)-2-Benzyl-3-(methylthio)propionic acid 在 氯化亚砜 作用下， 以97%的产率得到2-benzyl-3-methylthiopropanoic acid methyl ester
  参考文献：
  名称：

  Optically active 2-benzyl-3-methanesulfinylpropanoic acid: Synthesis and evaluation as inhibitors for carboxypeptidase A

  摘要：

  All four possible stereomers of 2-benzyl-3-methanesulfinylpropanoic acid were synthesized and evaluated as inhibitors for carboxypeptidase A to find that the isomer having the (2S,4S)-configuration is most potent followed by isomers of (2R,4S)- and (2S,4R)-configurations. The stereochemical preferences shown by the isomers of the inhibitor in binding to the enzyme suggest that the sulfoxide oxygen in the inhibitor fails to ligate the active site zinc ion but may form a hydrogen bond with the guanidinium moiety of Arg-127 like the carbonyl oxygen of scissile peptide bond of oligopeptide Substrate of the enzyme does. It may thus be inferred that a sulfoxide moiety may serve as an isosterer of a carboxamide moiety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00481-4

文献信息

• Optically active 2-benzyl-3-methanesulfinylpropanoic acid: Synthesis and evaluation as inhibitors for carboxypeptidase A
  作者：Jing-Yi Jin、Guan Rong Tian、Dong H Kim

  DOI：10.1016/s0968-0896(03)00481-4

  日期：2003.10

  All four possible stereomers of 2-benzyl-3-methanesulfinylpropanoic acid were synthesized and evaluated as inhibitors for carboxypeptidase A to find that the isomer having the (2S,4S)-configuration is most potent followed by isomers of (2R,4S)- and (2S,4R)-configurations. The stereochemical preferences shown by the isomers of the inhibitor in binding to the enzyme suggest that the sulfoxide oxygen in the inhibitor fails to ligate the active site zinc ion but may form a hydrogen bond with the guanidinium moiety of Arg-127 like the carbonyl oxygen of scissile peptide bond of oligopeptide Substrate of the enzyme does. It may thus be inferred that a sulfoxide moiety may serve as an isosterer of a carboxamide moiety. (C) 2003 Elsevier Ltd. All rights reserved.