3,4'-bis-(2-methoxycarbonylethyl)-4,3'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole-5,5'-dicarbaldehyde | 58950-56-4

• 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: 3,4'-bis-(2-methoxycarbonylethyl)-4,3'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole-5,5'-dicarbaldehyde
• 英文别名: 5,5'-diformyl-3',4-di-(2-methoxycarbonylethyl)-3,4'-dimethoxycarbonylmethyl-2,2'-methylenedi-pyrrole；3,3'-(5,2'-diformyl-4,4'-bis-methoxycarbonylmethyl-2,5'-methanediyl-di-pyrrol-3,3'diyl)-bis-propionic acid dimethyl ester
• CAS: 58950-56-4
• 化学式: C₂₅H₃₀N₂O₁₀
• 分子量: 518.521
• InChiKey: FMLMXFUUSWQFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  170.92
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4'-bis-(2-methoxycarbonylethyl)-4,3'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole-5,5'-dicarbaldehyde 在 氢氧化钾 、 sodium amalgam 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 74.0h， 生成
  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：

  benzyl 5'-t.butyloxycarbonyl-4,3'-di(2-methoxycarbonylethyl)-3,4'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole-5-carboxylate 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 3,4'-bis-(2-methoxycarbonylethyl)-4,3'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole-5,5'-dicarbaldehyde
  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 16. Proof that the single intramolecular rearrangement leading to natural porphyrins (type-III) occurs at the tetrapyrrole level
  作者：Alan R. Battersby、Christopher J. R. Fookes、Mary J. Meegan、Edward McDonald、Hanns K. W. Wurziger

  DOI：10.1039/p19810002786

  日期：——

  established earlier is thus proved to take place at the tetrapyrole level. Synthesis of singly 13C-labelled bilane (2) followed by its enzymic conversion into uro'gen-III serves to register each of the pyrrole rings of the product relative to the initial bilane. Finally, methods for synthesis of the bilane are developed in two different doubly 13C-labelled forms to allow the following key points to be established

  未重排的氨基甲基胆烷（2）是通过合理的途径合成的，并被脱氨酶和辅酶合成，并协同作用转化为uro'gen-III（3）。因此证明了较早建立的单个重排步骤发生在四吡咯水平。单独合成13 C标记的胆烷（2），然后将其酶促转化为uro'gen-III，相对于初始胆烷来说，该产物的每个吡咯环均具有配准作用。最后，以两种不同的双13 C标记形式开发了合成胆烷的方法，从而可以通过13 C nmr光谱学在很大程度上确定以下关键点：（a）随着胆烷体系被转化为尿根-III，发生了末端环D的分子内重排，并且（b）线性四吡咯被完整地转化为尿根-III。