benzyl (2R,3S)-2-benzyl-3,4-epoxybutanoate | 172275-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2R,3S)-2-benzyl-3,4-epoxybutanoate
• 英文别名: benzyl (2R)-2-[(2S)-oxiran-2-yl]-3-phenylpropanoate
• CAS: 172275-58-0
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: QGTIORPQNQNFQR-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3S)-2-benzyl-3,4-epoxybutanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到(2R,3S)-2-benzyl-3,4-epoxybutanoic acid
  参考文献：
  名称：

  (2R, 3S)- and (2S, 3R)-2-Benzyl-3,4-epoxybutanoic acid as highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase a: design, asymmetric synthesis and inhibitory kinetics

  摘要：

  2-Benzyl-3,4-epoxybutanoic acid (BEBA) was studied as an irreversible inhibitor for the zinc-containing protease, carboxypeptidase A. Of four possible stereoisomers, those having a 2R,3S- and a 2S,3R-configuration inhibited carboxypeptidase A in a time dependent manner. The latter compound that belongs to the D series is more effective with a k(inact)/K-i value of 139.5 dm(3) mol(-1) s(-1) than the former having a K-inact/K-i value of 53.9 dm(3) mol(-1) s(-1). Partition ratios, fore (2R,3S)- and (2S,3R)-BEBA were determined as 1.01 and 0.53, respectively. The observed kinetic parameters reveal that both are highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase A. Details of the kinetic analyses, design principles and asymmetric syntheses of these inactivators are described.

  DOI：

  10.1039/p19950002877
• 作为产物：
  描述：

  dibenzyl (2S,3R)-2-benzyl-3-hydroxysuccinate 在 吡啶 、 sodium tetrahydroborate 、 二甲基硫 、 硼烷 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 49.5h， 生成 benzyl (2R,3S)-2-benzyl-3,4-epoxybutanoate
  参考文献：
  名称：

  (2R, 3S)- and (2S, 3R)-2-Benzyl-3,4-epoxybutanoic acid as highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase a: design, asymmetric synthesis and inhibitory kinetics

  摘要：

  2-Benzyl-3,4-epoxybutanoic acid (BEBA) was studied as an irreversible inhibitor for the zinc-containing protease, carboxypeptidase A. Of four possible stereoisomers, those having a 2R,3S- and a 2S,3R-configuration inhibited carboxypeptidase A in a time dependent manner. The latter compound that belongs to the D series is more effective with a k(inact)/K-i value of 139.5 dm(3) mol(-1) s(-1) than the former having a K-inact/K-i value of 53.9 dm(3) mol(-1) s(-1). Partition ratios, fore (2R,3S)- and (2S,3R)-BEBA were determined as 1.01 and 0.53, respectively. The observed kinetic parameters reveal that both are highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase A. Details of the kinetic analyses, design principles and asymmetric syntheses of these inactivators are described.

  DOI：

  10.1039/p19950002877

文献信息

• (2R, 3S)- and (2S, 3R)-2-Benzyl-3,4-epoxybutanoic acid as highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase a: design, asymmetric synthesis and inhibitory kinetics
  作者：Soo Suk Lee、Zhi-Hong Li、Dong Ha Lee、Dong H. Kim

  DOI：10.1039/p19950002877

  日期：——

  2-Benzyl-3,4-epoxybutanoic acid (BEBA) was studied as an irreversible inhibitor for the zinc-containing protease, carboxypeptidase A. Of four possible stereoisomers, those having a 2R,3S- and a 2S,3R-configuration inhibited carboxypeptidase A in a time dependent manner. The latter compound that belongs to the D series is more effective with a k(inact)/K-i value of 139.5 dm(3) mol(-1) s(-1) than the former having a K-inact/K-i value of 53.9 dm(3) mol(-1) s(-1). Partition ratios, fore (2R,3S)- and (2S,3R)-BEBA were determined as 1.01 and 0.53, respectively. The observed kinetic parameters reveal that both are highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase A. Details of the kinetic analyses, design principles and asymmetric syntheses of these inactivators are described.