1-dibenzyl 2-dimethyl 4,4'-((3R,8R)-8-formamido-3-((2-methoxy-2-oxoethyl)carbamoyl)-9,12-dioxo-13-oxa-5,6-dithia-2,10-diazatetradecanoyl)(2S,2'S,4S,4'S)-bis(pyrrolidine-1,2-dicarboxylate) | 586396-31-8

• 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: 1-dibenzyl 2-dimethyl 4,4'-((3R,8R)-8-formamido-3-((2-methoxy-2-oxoethyl)carbamoyl)-9,12-dioxo-13-oxa-5,6-dithia-2,10-diazatetradecanoyl)(2S,2'S,4S,4'S)-bis(pyrrolidine-1,2-dicarboxylate)
• CAS: 586396-31-8
• 化学式: C₄₂H₅₂N₆O₁₆S₂
• 分子量: 961.037
• InChiKey: GFNZQVCSMDPYAA-JNRWAQIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  66.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  280.68
• 氢给体数：
  4.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1-dibenzyl 2-dimethyl 4,4'-((3R,8R)-8-formamido-3-((2-methoxy-2-oxoethyl)carbamoyl)-9,12-dioxo-13-oxa-5,6-dithia-2,10-diazatetradecanoyl)(2S,2'S,4S,4'S)-bis(pyrrolidine-1,2-dicarboxylate) 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以96%的产率得到(2'S,4S,4'S)-4,4'-((((2R,2'R)-disulfanediylbis(3-((carboxymethyl)amino)-3-oxopropane-1,2-diyl))bis(azanediyl))bis(carbonyl))bis(1-((benzyloxy)carbonyl)-L-proline)
  参考文献：
  名称：

  Proline–Glutamate Chimeras in Isopeptides. Synthesis and Biological Evaluation of Conformationally Restricted Glutathione Analogues

  摘要：

  The two novel diastereoisomeric glutathione analogues I and 2 have been designed and synthesized by replacing the native gamma-glutamylic moiety with the conformational rigid skeleton of cis- or trans-4-carboxy-L-proline residue. Both analogues have been obtained by following the solution phase peptide chemistry methodologies and final reduction of the corresponding disulfide forms 13 and 14. The two analogues 1 and 2 have been tested towards gamma-glutamyltranspeptidase (gamma-GT) and human glutathione S-transferase (hGST P1-1). Both analogues 1 and 2 are completely resistant to enzymatic degradation by gamma-GT. The S-transferase utilizes the analogue 2 as a good substrate while is unable to bind the analogue 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00041-5
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline dimethyl ester 在 sodium hydroxide 、 碘 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.5h， 生成 1-dibenzyl 2-dimethyl 4,4'-((3R,8R)-8-formamido-3-((2-methoxy-2-oxoethyl)carbamoyl)-9,12-dioxo-13-oxa-5,6-dithia-2,10-diazatetradecanoyl)(2S,2'S,4S,4'S)-bis(pyrrolidine-1,2-dicarboxylate)
  参考文献：
  名称：

  Proline–Glutamate Chimeras in Isopeptides. Synthesis and Biological Evaluation of Conformationally Restricted Glutathione Analogues

  摘要：

  The two novel diastereoisomeric glutathione analogues I and 2 have been designed and synthesized by replacing the native gamma-glutamylic moiety with the conformational rigid skeleton of cis- or trans-4-carboxy-L-proline residue. Both analogues have been obtained by following the solution phase peptide chemistry methodologies and final reduction of the corresponding disulfide forms 13 and 14. The two analogues 1 and 2 have been tested towards gamma-glutamyltranspeptidase (gamma-GT) and human glutathione S-transferase (hGST P1-1). Both analogues 1 and 2 are completely resistant to enzymatic degradation by gamma-GT. The S-transferase utilizes the analogue 2 as a good substrate while is unable to bind the analogue 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00041-5