5'-hydroxyimidazolepropionate | 78957-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5'-hydroxyimidazolepropionate
• 英文别名: 3-(5-oxo-4,5-dihydro-1(3)H-imidazol-4-yl)-propionic acid；3-(4-hydroxy-1H-imidazol-5-yl)propanoic acid
• CAS: 78957-12-7
• 化学式: C₆H₈N₂O₃
• 分子量: 156.141
• InChiKey: OWVUGOIAIJBQNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式尿刊酸 在 urocanate hydratase 作用下， 以 水 为溶剂， 生成 5'-hydroxyimidazolepropionate
  参考文献：
  名称：

  Mechanism of Action of Urocanase: Ruling Out a 1,5 Sigmatropic H-Shift in the Intermediate NAD+ Urocanate Adduct

  摘要：

  The tightly bound NAD(+) in urocanase forms a covalent adduct with the inhibitor imidazole propionate and most likely also with the substrate urocanate. Subsequent tautomerizations and cleavage of the adduct lead eventually to the product, 5-hydroxyimidazole propionate. The possibility that the H4 atom of the nicotinamide moiety undergoes a 1,5 sigmatropic H-shift in one of the intermediates has been investigated by deuterium labeling. No incorporation of solvent deuterium into position 4 of the nicotinamide moiety could be detected, which rules out a 1,5-sigmatropic shift of the H4 atom. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1030