(S,E)-4-氨基-5-氟-2-戊烯酸盐酸盐 | 103500-21-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S,E)-4-氨基-5-氟-2-戊烯酸盐酸盐
• 英文名称: (S,E)-4-amino-5-fluoro-2-pentenoic acid hydrochloride
• 英文别名: (E,4S)-4-amino-5-fluoropent-2-enoic acid;hydrochloride
• CAS: 103500-21-6
• 化学式: C₅H₈FNO₂*ClH
• 分子量: 169.583
• InChiKey: FZOZYHLZJRUJDO-MXXSFESMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-4-amino-5-fluoropentanoic acid 在 盐酸 、 正丁基锂 、 氯化亚砜 、 四甲基乙二胺 、 双氧水 、 三乙胺 、 六甲基二硅氮烷 、 三氟乙酸 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 16.17h， 生成 (S,E)-4-氨基-5-氟-2-戊烯酸盐酸盐
  参考文献：
  名称：

  Inactivation of .gamma.-aminobutyric acid aminotransferase by (S,E)-4-amino-5-fluoropent-2-enoic acid and effect on the enzyme of (E)-3-(1-aminocyclopropyl)-2-propenoic acid

  摘要：

  (S,E)-4-Amino-5-fluoropent-2-enoic acid (6) is synthesized in six steps starting from the known gamma-aminobutyric acid aminotransferase (gamma-Abu-T) inactivator, (S)-4-amino-5-fluoropentanoic acid (1). Compound 6 is a mechanism-based inactivator of gamma-Abu-T: time-dependent inactivation is saturatable and protected by substrate; thiols do not protect the enzyme from inactivation; no enzyme activity returns upon dialysis. This compound (6) binds 50 times more tightly to gamma-Abu-T than does the saturated analogue (1). No transamination of 6 occurs prior to inactivation. However, five molecules of 6 are required to inactivate the enzyme with concomitant release of five fluoride ions. Therefore, four molecules are being converted to product for each inactivation event. (E)-3-(1-Aminocyclopropyl)-2-propenoic acid is synthesized in seven steps from 1-aminocyclopropanecarboxylic acid. It is prepared as a cyclopropyl derivative of the proposed intermediate in the inactivation of gamma-Abu-T by 6. The cyclopropyl derivative, however, is a noncompetitive inhibitor and does not inactivate the enzyme. This study shows the usefulness and hazards of incorporation of a trans double bond into potential gamma-Abu-T inactivators.

  DOI：

  10.1021/jm00160a007

文献信息

• US4528028A
  申请人：——

  公开号：US4528028A

  公开（公告）日：1985-07-09
• Inactivation of .gamma.-aminobutyric acid aminotransferase by (S,E)-4-amino-5-fluoropent-2-enoic acid and effect on the enzyme of (E)-3-(1-aminocyclopropyl)-2-propenoic acid
  作者：Richard B. Silverman、Benedict J. Invergo、Jacob Mathew

  DOI：10.1021/jm00160a007

  日期：1986.10

  (S,E)-4-Amino-5-fluoropent-2-enoic acid (6) is synthesized in six steps starting from the known gamma-aminobutyric acid aminotransferase (gamma-Abu-T) inactivator, (S)-4-amino-5-fluoropentanoic acid (1). Compound 6 is a mechanism-based inactivator of gamma-Abu-T: time-dependent inactivation is saturatable and protected by substrate; thiols do not protect the enzyme from inactivation; no enzyme activity returns upon dialysis. This compound (6) binds 50 times more tightly to gamma-Abu-T than does the saturated analogue (1). No transamination of 6 occurs prior to inactivation. However, five molecules of 6 are required to inactivate the enzyme with concomitant release of five fluoride ions. Therefore, four molecules are being converted to product for each inactivation event. (E)-3-(1-Aminocyclopropyl)-2-propenoic acid is synthesized in seven steps from 1-aminocyclopropanecarboxylic acid. It is prepared as a cyclopropyl derivative of the proposed intermediate in the inactivation of gamma-Abu-T by 6. The cyclopropyl derivative, however, is a noncompetitive inhibitor and does not inactivate the enzyme. This study shows the usefulness and hazards of incorporation of a trans double bond into potential gamma-Abu-T inactivators.