N-[2-cyanoethyl(n-butyl)phosphinyl]-L-glutamic acid dimethyl ester | 253269-38-4

• 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: N-[2-cyanoethyl(n-butyl)phosphinyl]-L-glutamic acid dimethyl ester
• 英文别名: dimethyl (2S)-2-[[butyl(2-cyanoethoxy)phosphoryl]amino]pentanedioate
• CAS: 253269-38-4
• 化学式: C₁₄H₂₅N₂O₆P
• 分子量: 348.336
• InChiKey: QZEIKNORBMLYBL-AKYMPMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[2-cyanoethyl(n-butyl)phosphinyl]-L-glutamic acid dimethyl ester 在 劳森试剂 作用下， 生成 N-[2-cyanoethyl(n-butyl)phosphinothioyl]-L-glutamic acid dimethyl ester
  参考文献：
  名称：

  Competitive inhibition of a glutamate carboxypeptidase by phosphonamidothionate derivatives of glutamic acid

  摘要：

  Several N-thiophosphonyl-glutamates were found to be potent competitive inhibitors of a zinc-dependent glutamyl hydrolase, carboxypeptidase G (CPG). Weak inhibition exhibited by an analogous N-phosphonyl-glutamate suggests that the enhanced potency of the phosphonamidothioates is due to the presence of their sulfur ligand and its favorable interactions with active site features, presumably zinc(II). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00198-5
• 作为产物：
  描述：

  谷氨酸二甲酯 、 在 二乙醇胺 作用下， 生成 N-[2-cyanoethyl(n-butyl)phosphinyl]-L-glutamic acid dimethyl ester
  参考文献：
  名称：

  Competitive inhibition of a glutamate carboxypeptidase by phosphonamidothionate derivatives of glutamic acid

  摘要：

  Several N-thiophosphonyl-glutamates were found to be potent competitive inhibitors of a zinc-dependent glutamyl hydrolase, carboxypeptidase G (CPG). Weak inhibition exhibited by an analogous N-phosphonyl-glutamate suggests that the enhanced potency of the phosphonamidothioates is due to the presence of their sulfur ligand and its favorable interactions with active site features, presumably zinc(II). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00198-5

文献信息

• Synthesis of <i>N</i>-Phosphonamidothionate Derivatives of Glutamic Acid
  作者：Haiyan Lu、Karyn L. Mlodnosky、Trang T. Dinh、Azar Dastgah、Vinh Q. Lam、Clifford E. Berkman

  DOI：10.1021/jo991090x

  日期：1999.11.1
• Competitive inhibition of a glutamate carboxypeptidase by phosphonamidothionate derivatives of glutamic acid
  作者：Chester E. Rodriguez、Haiyan Lu、Trang T. Ding、Karyn L. Mlodnosky、Azar Dastgah、Vinh Q. Lam、C.Blake Nichols、Clifford E. Berkman

  DOI：10.1016/s0960-894x(99)00198-5

  日期：1999.5

  Several N-thiophosphonyl-glutamates were found to be potent competitive inhibitors of a zinc-dependent glutamyl hydrolase, carboxypeptidase G (CPG). Weak inhibition exhibited by an analogous N-phosphonyl-glutamate suggests that the enhanced potency of the phosphonamidothioates is due to the presence of their sulfur ligand and its favorable interactions with active site features, presumably zinc(II). (C) 1999 Elsevier Science Ltd. All rights reserved.