3,3',3'',3'''-[3,8,13,17-四(羧甲基)-5,10,15,20,22,24-六氢卟啉-2,7,12,18-四基]四丙酸 | 53790-14-0

• 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
• 中文名称: 3,3',3'',3'''-[3,8,13,17-四(羧甲基)-5,10,15,20,22,24-六氢卟啉-2,7,12,18-四基]四丙酸
• 英文名称: Uroporphyrinogen-IV
• 英文别名: 3-[7,13,18-Tris(2-carboxyethyl)-3,8,12,17-tetrakis(carboxymethyl)-5,10,15,20,21,22,23,24-octahydroporphyrin-2-yl]propanoic acid；3-[7,13,18-tris(2-carboxyethyl)-3,8,12,17-tetrakis(carboxymethyl)-5,10,15,20,21,22,23,24-octahydroporphyrin-2-yl]propanoic acid
• CAS: 53790-14-0
• 化学式: C₄₀H₄₄N₄O₁₆
• 分子量: 836.807
• InChiKey: WWBIOKCOXCXEAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  362
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  甲醇 、 S-腺苷-L-蛋氨酸 、 3,3',3'',3'''-[3,8,13,17-四(羧甲基)-5,10,15,20,22,24-六氢卟啉-2,7,12,18-四基]四丙酸 在 antifoam 204 、 magnesium chloride Tris-HCl buffer 、 Escherichia coli CR₃₉₅ lysate 、 potassium chloride 、 硫酸 作用下， 反应 38.0h， 以7%的产率得到
  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
• 作为产物：
  描述：

  在 氢氧化钾 、 sodium amalgam 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 3,3',3'',3'''-[3,8,13,17-四(羧甲基)-5,10,15,20,22,24-六氢卟啉-2,7,12,18-四基]四丙酸
  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

• Biosynthesis of porphyrins and related macrocycles. Part 15. Chemical and enzymic formation of uroporphyrinogen isomers from unrearranged aminomethylpyrromethane: separation of isomeric coproporphyrin esters
  作者：Alan R. Battersby、Dennis G. Buckley、David W. Johnson、Lewis N. Mander、Edward McDonald、D. Clive Williams

  DOI：10.1039/p19810002779

  日期：——

  traces of uro'gen-III are formed. Uro'gen-I is produced via a tetrapyrrolic (bilane) intermediate and when the deaminase–cosynthetase enzyme system from Euglena gracilis is present, this intermediate is converted into uro'gen-III. The rearrangement step for this conversion has the same characteristics found earlier for the natural biosynthetic process from porphobilinogen. Pyrromethane (1) is not a direct

  未重排的吡咯甲烷（1）主要化学转化为具有少量uro'gen-IV的uro'gen-I，但仅形成了痕量的uro'gen-III。Uro'gen-I是通过四吡咯烷（乙撑）中间体生产的，当存在来自Euglena gracilis的脱氨基酶-合成酶体系时，该中间体会转化为uro'gen-III。该转化的重排步骤具有较早的从胆色素原的天然生物合成过程中发现的特征。吡咯甲烷（1）并不是uro'gen-III的直接生物合成前体，其原因尚可理解。
• Battersby, Alan R.; Fookes, Christopher J. R.; Matcham, George W. J., Angewandte Chemie, 1981, vol. 93, # 3, p. 290 - 292
  作者：Battersby, Alan R.、Fookes, Christopher J. R.、Matcham, George W. J.、Pandey, Pramod S.

  DOI：——

  日期：——
• 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.