4,6,7-tris-(2-methoxycarbonylethyl)-5-methoxycarbonylmethyl-1,3,8-trimethyl-2-vinylporphyrin | 61316-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 4,6,7-tris-(2-methoxycarbonylethyl)-5-methoxycarbonylmethyl-1,3,8-trimethyl-2-vinylporphyrin
• 英文别名: dehydroisocoproporphyrin tetramethyl ester；3,3',3''-(3-methoxycarbonylmethyl-8,13,17-trimethyl-12-vinyl-21H,23H-porphine-2,7,18-triyl)-tris-propionic acid trimethyl ester
• CAS: 61316-59-4
• 化学式: C₄₀H₄₄N₄O₈
• 分子量: 708.811
• InChiKey: VYZXQEJYMBRRLI-JFYUAMAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  52.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  162.56
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  3-[7,12,18-Tris-(2-carboxy-ethyl)-3-carboxymethyl-8,13,17-trimethyl-porphyrinogen-2-yl]-propionic acid 在 咪唑 、 硫酸 、 氧气 、 coproporphyrinogen oxidase 作用下， 以 水 为溶剂， 反应 17.0h， 生成 4,6,7-tris-(2-methoxycarbonylethyl)-5-methoxycarbonylmethyl-1,3,8-trimethyl-2-vinylporphyrin
  参考文献：
  名称：

  Metabolism of pentacarboxylate porphyrinogens by highly purified human coproporphyrinogen oxidase: Further evidence for the existence of an abnormal pathway for heme biosynthesis

  摘要：

  An abnormal series of porphyrin tetracarboxylic acids known as the isocoproporphyrins, are commonly excreted by patients suffering from the disease porphyria cutanea tarda (PCT). These porphyrins appear to arise by bacterial degradation of dehydroisocoproporphyrinogen that is generated by the premature metabolism of the normal pentacarboxylate intermediate (5dab) by coproporphyrinogen oxidase (copro'gen oxidase). This porphyrinogen can be further metabolized by uroporphyrinogen decarboxylase to give harderoporphyrinogen, one of the usual intermediates in heme biosynthesis. Therefore, it is possible that some of the heme formed under abnormal conditions may originate from the 'isocopro-type' porphyrinogen intermediate. In order to investigate the feasibility of alternative pathways for heme biosynthesis, the four type III pentacarboxylate isomeric porphyrinogens were incubated with purified, cloned human copro'gen oxidase at 37 degrees C with various substrate concentrations under initial velocity conditions. Of the four isomers, only 5dab was a substrate for copro'gen oxidase and this gave dehydroisocoproporphyrin. The structure of the related porphyrin tetrarnethyl ester was confirmed by proton NMR spectroscopy and mass spectrometry. The Km value for proto'gen-IX formation from copro'gen, an indicator of molecular recognition, was similar to the K-m value for monovinyl product formation with 5dab, although copro'gen-III has an approximately twofold higher K-cat value. Although 5dab is a slightly poorer substrate than copro'gen-111, these results support the hypothesis that an abnormal route for heme biosynthesis is possible in humans suffering from PCT or related syndromes such as hexachlorobenzene poisoning. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.051