3-[7,12,18-tris(2-carboxyethyl)-8,13,17-tris(carboxymethyl)-3-methyl-5,10,15,20,21,22,23,24-octahydroporphyrin-2-yl]propanoic acid | 55538-43-7

• 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: 3-[7,12,18-tris(2-carboxyethyl)-8,13,17-tris(carboxymethyl)-3-methyl-5,10,15,20,21,22,23,24-octahydroporphyrin-2-yl]propanoic acid
• CAS: 55538-43-7
• 化学式: C₃₉H₄₄N₄O₁₄
• 分子量: 792.797
• InChiKey: ASFNCEZZTQUPIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  324.26
• 氢给体数：
  11.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-[7,12,18-tris(2-carboxyethyl)-8,13,17-tris(carboxymethyl)-3-methyl-5,10,15,20,21,22,23,24-octahydroporphyrin-2-yl]propanoic acid 以0.5%的产率得到
  参考文献：
  名称：

  维生素B 12的生物合成：什么时候乙酸酯脱羧生成维生素的12β-甲基基团？

  摘要：

  precorrin-3（5）的芳香形式的12-甲基类似物（13）是通过12-de羧基-尿'-gen-III（2）的酶C-甲基化制备的，并用于掺入实验，表明脱羧C 17甲基化后，B 12-生物合成中的12-乙酸酯残基发生。

  DOI：

  10.1039/c39880001117
• 作为产物：
  描述：

  在 sodium amalgam 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-[7,12,18-tris(2-carboxyethyl)-8,13,17-tris(carboxymethyl)-3-methyl-5,10,15,20,21,22,23,24-octahydroporphyrin-2-yl]propanoic acid
  参考文献：
  名称：

  Synthesis of substrate analogs of methyltransferases in the vitamin B12 biosynthetic pathway and characterization of their enzymatic products

  摘要：

  The specificity toward substrate analogs of the first two methyltransferases in the vitamin B-12 biosynthetic pathway was probed with 15 synthetic porphyrinogens. Several novel methylated chlorins and isobacteriochlorins were isolated and characterized, suggesting the same methylation sequence C-2 > C-7 > C-20 as for the natural substrate, uro'gen III. The results allow us to narrow down possible structural requirements concerning substrate recognition by the methyltransferase enzymes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.041

文献信息

• Synthesis of substrate analogs of methyltransferases in the vitamin B12 biosynthetic pathway and characterization of their enzymatic products
  作者：Clotilde Pichon-Santander、Patricio J. Santander、A. Ian Scott

  DOI：10.1016/j.bmc.2006.01.041

  日期：2006.6

  The specificity toward substrate analogs of the first two methyltransferases in the vitamin B-12 biosynthetic pathway was probed with 15 synthetic porphyrinogens. Several novel methylated chlorins and isobacteriochlorins were isolated and characterized, suggesting the same methylation sequence C-2 > C-7 > C-20 as for the natural substrate, uro'gen III. The results allow us to narrow down possible structural requirements concerning substrate recognition by the methyltransferase enzymes. (c) 2006 Elsevier Ltd. All rights reserved.
• Biosynthesis of vitamin B₁₂: when is the 12β-methyl group of the vitamin generated by acetate decarboxylation?
  作者：Francis Blanche、Sheetal Handa、Denis Thibaut、Colin L. Gibson、Finian J. Leeper、Alan R. Battersby

  DOI：10.1039/c39880001117

  日期：——

  analogue (13) of the aromatised form of precorrin-3(5) has been prepared by enzymic C-methylation of 12-decarboxy-uro'gen-III (2) and is used for incorporation experiments which indicate that decarboxylation of the 12-acetate residue in B12-biosynthesis occurs after C-17 methylation.

  precorrin-3（5）的芳香形式的12-甲基类似物（13）是通过12-de羧基-尿'-gen-III（2）的酶C-甲基化制备的，并用于掺入实验，表明脱羧C 17甲基化后，B 12-生物合成中的12-乙酸酯残基发生。