2-(4-氨基-5-羟基-5-氧代戊基)氮丙啶-2-羧酸 | 125509-89-9

• 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
• 中文名称: 2-(4-氨基-5-羟基-5-氧代戊基)氮丙啶-2-羧酸
• 中文别名: 丁基2,3-二氯丙酸盐
• 英文名称: 2-(4-amino-4-carboxybutyl)-2-aziridinecarboxylic acid
• 英文别名: 2-(4-amino-4-carboxybutyl)aziridine-2-carboxylic acid
• CAS: 125509-89-9
• 化学式: C₈H₁₄N₂O₄
• 分子量: 202.21
• InChiKey: PZLRXNWCQLUSBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-氨基-5-羟基-5-氧代戊基)氮丙啶-2-羧酸 在 sodium hydroxide 作用下， 反应 6.0h， 生成 2-(4-amino-4-carboxybutyl)-2-aziridinecarboxylic acid disodium salt
  参考文献：
  名称：

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid. A potent irreversible inhibitor of diaminopimelic acid epimerase. Spontaneous formation from .alpha.-(halomethyl)diaminopimelic acids

  摘要：

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid (3) (aziridino-DAP) was identified as the product of spontaneous hydrolysis of alpha-(halomethyl)diaminopimelic acids (alpha-halomethyl-DAPs) 2a-c. Under physiological conditions, 3 is an extremely potent irreversible inhibitor of the bacterial enzyme diaminopimelic acid epimerase (DAP-epimerase; EC 5.1.1.7). This unusual mode of action of an alpha-halomethyl amino acid with a non-pyridoxal enzyme is investigated. Synthesis and characterization of 2a-c and 3, kinetics of spontaneous formation of 3 from alpha-halomethyl-DAPs, and kinetics of enzyme inhibition by both 3 and by alpha-halomethyl-DAPs are reported.

  DOI：

  10.1021/jm00170a018
• 作为产物：
  描述：

  2,6-Diamino-2-chloromethyl-heptanedioic acid 生成 2-(4-氨基-5-羟基-5-氧代戊基)氮丙啶-2-羧酸
  参考文献：
  名称：

  GERHART, FRITZ;HIGGINS, WILLIAM;TARDIF, CHANTAL;DUCEP, JEAN-BERNARD, J. MED. CHEM., 33,(1990) N, C. 2157-2162

  摘要：

  DOI：

文献信息

• GERHART, FRITZ;HIGGINS, WILLIAM;TARDIF, CHANTAL;DUCEP, JEAN-BERNARD, J. MED. CHEM., 33,(1990) N, C. 2157-2162
  作者：GERHART, FRITZ、HIGGINS, WILLIAM、TARDIF, CHANTAL、DUCEP, JEAN-BERNARD

  DOI：——

  日期：——
• 2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid. A potent irreversible inhibitor of diaminopimelic acid epimerase. Spontaneous formation from .alpha.-(halomethyl)diaminopimelic acids
  作者：Fritz Gerhart、William Higgins、Chantal Tardif、Jean Bernard Ducep

  DOI：10.1021/jm00170a018

  日期：1990.8

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid (3) (aziridino-DAP) was identified as the product of spontaneous hydrolysis of alpha-(halomethyl)diaminopimelic acids (alpha-halomethyl-DAPs) 2a-c. Under physiological conditions, 3 is an extremely potent irreversible inhibitor of the bacterial enzyme diaminopimelic acid epimerase (DAP-epimerase; EC 5.1.1.7). This unusual mode of action of an alpha-halomethyl amino acid with a non-pyridoxal enzyme is investigated. Synthesis and characterization of 2a-c and 3, kinetics of spontaneous formation of 3 from alpha-halomethyl-DAPs, and kinetics of enzyme inhibition by both 3 and by alpha-halomethyl-DAPs are reported.