[3,3-(2)H2]-5-aminolaevulinic acid

• 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: [3,3-(2)H2]-5-aminolaevulinic acid
• 英文别名: [3,3-(2)H2]ALA；5-Amino-3,3-dideuterio-4-oxopentanoic acid
• 化学式: C₅H₉NO₃
• 分子量: 133.115
• InChiKey: ZGXJTSGNIOSYLO-DICFDUPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3,3-(2)H2]-5-aminolaevulinic acid 在 bovine liver porphobilinogen synthase 作用下， 生成
  参考文献：
  名称：

  Stereochemistry and mechanism of the conversion of 5-aminolaevulinic acid into porphobilinogen catalysed by porphobilinogen synthaseElectronic supplementary information (ESI) available: purification and assay protocols and plots of enzymic activity vs. substrate concentration. See http://www.rsc.org/suppdata/ob/b3/b302509h/

  摘要：

  合成了(3R)-和(3S)-脱胎形式的 5-aminolaevulinic acid，(3R)-形式的 5-aminolaevulinic acid 在与牛肝脏和枯草芽孢杆菌中的门冬氨酸合成酶孵育时显示出明显更大的同位素效应；基于这一点和现有的晶体结构，提出了酶促反应的改进机制。

  DOI：

  10.1039/b302509h
• 作为产物：
  描述：

  5-氨基乙酰丙酸 在 吡啶 、 diclazuril 、 水 、 重水 、 吡哆醛 作用下， 生成 [3,3-(2)H2]-5-aminolaevulinic acid
  参考文献：
  名称：

  Deuterium isotope effects on porphobilinogen synthesis catalysed by 5-aminolaevulinic acid dehydratase

  摘要：

  Deuteriation of 5-aminolaevulinic acid (ALA) at C-5 has no effect on the rate of porphobilinogen synthesis by ALA dehydratase from Bacillus subtilis but deuteriation at C-3 gave isotope effects on k(cat) and k(cat)/K-M of 3.4 and 2.3 respectively. Reisolated ALA after 50% reaction shows no significant loss of deuterium at C-3, indicating that it is probably the first deprotonation at this carbon which is rate-determining. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00199-0

文献信息

• Stereochemistry and mechanism of the conversion of 5-aminolaevulinic acid into porphobilinogen catalysed by porphobilinogen synthaseElectronic supplementary information (ESI) available: purification and assay protocols and plots of enzymic activity vs. substrate concentration. See http://www.rsc.org/suppdata/ob/b3/b302509h/
  作者：Catherine E. Goodwin、Finian J. Leeper

  DOI：10.1039/b302509h

  日期：2003.4.23

  (3R)- and (3S)-Deuteriated forms of 5-aminolaevulinic acid have been synthesised and the (3R)-form shows a significantly larger isotope effect when incubated with porphobilinogen synthase from bovine liver and from Bacillus subtilis; based on this and on available crystal structures, a modified mechanism for the enzymic reaction is proposed.

  合成了(3R)-和(3S)-脱胎形式的 5-aminolaevulinic acid，(3R)-形式的 5-aminolaevulinic acid 在与牛肝脏和枯草芽孢杆菌中的门冬氨酸合成酶孵育时显示出明显更大的同位素效应；基于这一点和现有的晶体结构，提出了酶促反应的改进机制。
• Deuterium isotope effects on porphobilinogen synthesis catalysed by 5-aminolaevulinic acid dehydratase
  作者：Diana Appleton、Finian J. Leeper

  DOI：10.1016/0960-894x(96)00199-0

  日期：1996.6

  Deuteriation of 5-aminolaevulinic acid (ALA) at C-5 has no effect on the rate of porphobilinogen synthesis by ALA dehydratase from Bacillus subtilis but deuteriation at C-3 gave isotope effects on k(cat) and k(cat)/K-M of 3.4 and 2.3 respectively. Reisolated ALA after 50% reaction shows no significant loss of deuterium at C-3, indicating that it is probably the first deprotonation at this carbon which is rate-determining. Copyright (C) 1996 Elsevier Science Ltd