3-<(ethoxycarbonyl)methyl>-3',4-bis<2-(methoxycarbonyl)ethyl>-4'-methyl-2,2'-dipyrrylmethane-5,5'-dicarboxylic acid | 220720-54-7

• 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-<(ethoxycarbonyl)methyl>-3',4-bis<2-(methoxycarbonyl)ethyl>-4'-methyl-2,2'-dipyrrylmethane-5,5'-dicarboxylic acid
• 英文别名: 5-[[5-carboxy-3-(2-ethoxy-2-oxoethyl)-4-(3-methoxy-3-oxopropyl)-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 220720-54-7
• 化学式: C₂₄H₃₀N₂O₁₀
• 分子量: 506.51
• InChiKey: DXOVBUJESTUSHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-<(ethoxycarbonyl)methyl>-3',4-bis<2-(methoxycarbonyl)ethyl>-4'-methyl-2,2'-dipyrrylmethane-5,5'-dicarboxylic acid 在 硫酸 、 氢溴酸 、 溶剂黄146 、 三氟乙酸 、 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 3.25h， 生成 3,8,13,17-tetrakis<2-(methoxycarbonyl)ethyl>-7-<(methoxycarbonyl)methyl>-2,12,18-trimethylporphyrin
  参考文献：
  名称：

  Normal and Abnormal Heme Biosynthesis. 2.¹ Synthesis and Metabolism of Type-III Pentacarboxylic Porphyrinogens:  Further Experimental Evidence for the Enzymic Clockwise Decarboxylation of Uroporphyrinogen-III

  摘要：

  Uroporphyrinogen decarboxylase catalyses the sequential decarboxylation of uroporphyrinogen-III (1) to-give coproporphyrinogen-III (2), a precursor to the hemes and chlorophylls. This involves the decarboxylation of four nonequivalent acetate side chains to produce methyl units and in principle could take place by 24 different pathways involving up to 14 intermediary porphyrinogens. In the past, seemingly contradictory data have been presented that either support an ordered "clockwise" decarboxylation pathway or a random decarboxylation process. Four pentacarboxylate porphyrinogens might be involved immediately before the formation of 2, and these compounds have been synthesized as the corresponding porphyrin pentamethyl esters via tripyrrene and a,c-biladiene intermediates. Hydrolysis of the methyl esters and reduction with 3% sodium amalgam gave the required porphyrinogens, and these were incubated with crude enzyme preparations derived from chicken red cell hemolysates. One of these pentacarboxylate porphyrinogens (5dab) consistently proved to be a much better substrate than the other three, providing new support for the "clockwise" pathway for coproporphyrinogen-III formation.

  DOI：

  10.1021/jo9814748
• 作为产物：
  描述：

  methyl 4,6-dioxoheptanoate, keto-tautomer 在 palladium on activated charcoal lead(IV) acetate 、 Montmorillonite clay K₁₀ 、 氢气 、 sodium acetate 、 potassium carbonate 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 25.0~90.0 ℃ 、275.79 kPa 条件下， 反应 24.0h， 生成 3-<(ethoxycarbonyl)methyl>-3',4-bis<2-(methoxycarbonyl)ethyl>-4'-methyl-2,2'-dipyrrylmethane-5,5'-dicarboxylic acid
  参考文献：
  名称：

  Normal and Abnormal Heme Biosynthesis. 2.¹ Synthesis and Metabolism of Type-III Pentacarboxylic Porphyrinogens:  Further Experimental Evidence for the Enzymic Clockwise Decarboxylation of Uroporphyrinogen-III

  摘要：

  Uroporphyrinogen decarboxylase catalyses the sequential decarboxylation of uroporphyrinogen-III (1) to-give coproporphyrinogen-III (2), a precursor to the hemes and chlorophylls. This involves the decarboxylation of four nonequivalent acetate side chains to produce methyl units and in principle could take place by 24 different pathways involving up to 14 intermediary porphyrinogens. In the past, seemingly contradictory data have been presented that either support an ordered "clockwise" decarboxylation pathway or a random decarboxylation process. Four pentacarboxylate porphyrinogens might be involved immediately before the formation of 2, and these compounds have been synthesized as the corresponding porphyrin pentamethyl esters via tripyrrene and a,c-biladiene intermediates. Hydrolysis of the methyl esters and reduction with 3% sodium amalgam gave the required porphyrinogens, and these were incubated with crude enzyme preparations derived from chicken red cell hemolysates. One of these pentacarboxylate porphyrinogens (5dab) consistently proved to be a much better substrate than the other three, providing new support for the "clockwise" pathway for coproporphyrinogen-III formation.

  DOI：

  10.1021/jo9814748

文献信息

• Normal and Abnormal Heme Biosynthesis. 2.¹ Synthesis and Metabolism of Type-III Pentacarboxylic Porphyrinogens:  Further Experimental Evidence for the Enzymic Clockwise Decarboxylation of Uroporphyrinogen-III
  作者：Timothy D. Lash、Ukti N. Mani、Elizabeth A. Lyons、Pornlert Thientanavanich、Marjorie A. Jones

  DOI：10.1021/jo9814748

  日期：1999.1.1

  Uroporphyrinogen decarboxylase catalyses the sequential decarboxylation of uroporphyrinogen-III (1) to-give coproporphyrinogen-III (2), a precursor to the hemes and chlorophylls. This involves the decarboxylation of four nonequivalent acetate side chains to produce methyl units and in principle could take place by 24 different pathways involving up to 14 intermediary porphyrinogens. In the past, seemingly contradictory data have been presented that either support an ordered "clockwise" decarboxylation pathway or a random decarboxylation process. Four pentacarboxylate porphyrinogens might be involved immediately before the formation of 2, and these compounds have been synthesized as the corresponding porphyrin pentamethyl esters via tripyrrene and a,c-biladiene intermediates. Hydrolysis of the methyl esters and reduction with 3% sodium amalgam gave the required porphyrinogens, and these were incubated with crude enzyme preparations derived from chicken red cell hemolysates. One of these pentacarboxylate porphyrinogens (5dab) consistently proved to be a much better substrate than the other three, providing new support for the "clockwise" pathway for coproporphyrinogen-III formation.