(S)-N-(2-chloroethyl)-N-methylphenylalanine methyl ester | 338462-77-4

• 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: (S)-N-(2-chloroethyl)-N-methylphenylalanine methyl ester
• CAS: 338462-77-4
• 化学式: C₁₃H₁₈ClNO₂
• 分子量: 255.744
• InChiKey: SQCQAQBLMRGLKY-LBPRGKRZSA-N

物化性质

• 沸点：
  320.2±37.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-chloroethyl)-N-methylphenylalanine methyl ester 在 盐酸 作用下， 反应 1.0h， 生成 (2S)-2-[2-chloroethyl(methyl)amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  A new inhibitor design strategy for carboxypeptidase A as exemplified by N -(2-chloroethyl)- N -methylphenylalanine

  摘要：

  N-(2-Chloroethyl)-N-methylphenylalanine was designed and synthesized in an optically active form as a novel class of mechanism-based inactivator for carboxypeptidase A (CPA). It was anticipated that the chloroethylamino moiety of the CPA bound inhibitor undergoes an intramolecular S(N)2 reaction to generate a chemically reactive species (an aziridinium ion) which is expectedly subjected to a nucleophilic attack by the carboxylate of Glu-270, leading to covalent modification of the carboxylate. The irreversible nature of the inhibition of CPA by the inhibitor was supported by the kinetic data: the enzyme lost its enzymic activity in a time-dependent manner in the presence of the inhibitor and the inactivated CPA failed to regain the activity upon dialysis. Interestingly, the (R)-isomer that belongs to the D-series was more potent than its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00239-x
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 palladium on activated charcoal 氯化亚砜 、 sodium perchlorate 、 氢气 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.0h， 生成 (S)-N-(2-chloroethyl)-N-methylphenylalanine methyl ester
  参考文献：
  名称：

  A new inhibitor design strategy for carboxypeptidase A as exemplified by N -(2-chloroethyl)- N -methylphenylalanine

  摘要：

  N-(2-Chloroethyl)-N-methylphenylalanine was designed and synthesized in an optically active form as a novel class of mechanism-based inactivator for carboxypeptidase A (CPA). It was anticipated that the chloroethylamino moiety of the CPA bound inhibitor undergoes an intramolecular S(N)2 reaction to generate a chemically reactive species (an aziridinium ion) which is expectedly subjected to a nucleophilic attack by the carboxylate of Glu-270, leading to covalent modification of the carboxylate. The irreversible nature of the inhibition of CPA by the inhibitor was supported by the kinetic data: the enzyme lost its enzymic activity in a time-dependent manner in the presence of the inhibitor and the inactivated CPA failed to regain the activity upon dialysis. Interestingly, the (R)-isomer that belongs to the D-series was more potent than its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00239-x