2-(2-羧基乙基)-2-氮丙啶羧酸 | 157643-41-9

• 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-(2-羧基乙基)-2-氮丙啶羧酸
• 英文名称: 2-(2-carboxyethyl)aziridine-2-carboxylic acid
• CAS: 157643-41-9
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: FWZAXTATSWXGNX-UHFFFAOYSA-N

物化性质

• 沸点：
  413.2±30.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-羧基乙基)-2-氮丙啶羧酸 在 氘氧化钾 、 deuterated potassium dihydrogen phosphate 作用下， 以 重水 为溶剂， 反应 0.07h， 生成 2-(Aminomethyl)-5-oxotetrahydrofuran-2-carboxylic acid
  参考文献：
  名称：

  The synthesis and stability of aziridino-glutamate, an irreversible inhibitor of glutamate racemase

  摘要：

  Aziridino-glutamate (2-(2-carboxyethyl)aziridine-2-carboxylic acid, (+/-)4) was synthesized by heating alpha-fluoromethylglutamate in base. In neutral solution, 4 was shown to cyclize to the gamma-lactone 5 with a half life of 4 minutes. Aziridino-glutamate was shown to irreversibly inactivate glutamate racemase by alkylating an active site cysteine residue, Electrospray mass spectrometry was used to establish that a covalent bond had famed and that this bond protects one of the enzyme's two cysteine residues from reacting with iodoacetate under denaturing conditions.

  DOI：

  10.1016/s0040-4039(00)73115-7
• 作为产物：
  描述：

  (fluoromethyl)glutamic acid 在 氢氧化钾 作用下， 反应 1.5h， 生成 2-(2-羧基乙基)-2-氮丙啶羧酸
  参考文献：
  名称：

  The synthesis and stability of aziridino-glutamate, an irreversible inhibitor of glutamate racemase

  摘要：

  Aziridino-glutamate (2-(2-carboxyethyl)aziridine-2-carboxylic acid, (+/-)4) was synthesized by heating alpha-fluoromethylglutamate in base. In neutral solution, 4 was shown to cyclize to the gamma-lactone 5 with a half life of 4 minutes. Aziridino-glutamate was shown to irreversibly inactivate glutamate racemase by alkylating an active site cysteine residue, Electrospray mass spectrometry was used to establish that a covalent bond had famed and that this bond protects one of the enzyme's two cysteine residues from reacting with iodoacetate under denaturing conditions.

  DOI：

  10.1016/s0040-4039(00)73115-7

文献信息

• The synthesis and stability of aziridino-glutamate, an irreversible inhibitor of glutamate racemase
  作者：Martin E. Tanner、Shichang Miao

  DOI：10.1016/s0040-4039(00)73115-7

  日期：1994.6

  Aziridino-glutamate (2-(2-carboxyethyl)aziridine-2-carboxylic acid, (+/-)4) was synthesized by heating alpha-fluoromethylglutamate in base. In neutral solution, 4 was shown to cyclize to the gamma-lactone 5 with a half life of 4 minutes. Aziridino-glutamate was shown to irreversibly inactivate glutamate racemase by alkylating an active site cysteine residue, Electrospray mass spectrometry was used to establish that a covalent bond had famed and that this bond protects one of the enzyme's two cysteine residues from reacting with iodoacetate under denaturing conditions.