(S,S,S)-N-(2-benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carbonyl)-histidyl-prolinamide | 460326-94-7

• 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: (S,S,S)-N-(2-benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carbonyl)-histidyl-prolinamide
• CAS: 460326-94-7
• 化学式: C₂₃H₂₈N₆O₇S
• 分子量: 532.577
• InChiKey: MDVDOZLWDATCPH-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.35
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  184.86
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S,S,S)-N-(2-benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carbonyl)-histidyl-prolinamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到(S,S,S)-N-(isothiazolidine-1,1-dioxide-3-carbonyl)-histidyl-prolinamide
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel pyroglutamyl-modified TRH analogue

  摘要：

  The TRH analogue 3, incorporating the (S)-isothiazolidine-1,1-dioxide-3-carboxylic acid (I) moiety in place of the native L-pyroglutamic acid (pGlu) residue, has been synthesized and fully characterized by H-1 and C-13 NMR. The effects of replacing pGlu with its sulphonamido counterpart on biological activity have been investigated. This peptide, which is significantly stabilized towards hydrolysis by pyroglutamyl peptidase type I (PP I, EC 3.4.19.3), has shown to maintain in vitro prolactin-releasing activity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01232-6
• 作为产物：
  描述：

  (S)-2-Benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carboxylic acid 在 TEA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.33h， 生成 (S,S,S)-N-(2-benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carbonyl)-histidyl-prolinamide
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel pyroglutamyl-modified TRH analogue

  摘要：

  The TRH analogue 3, incorporating the (S)-isothiazolidine-1,1-dioxide-3-carboxylic acid (I) moiety in place of the native L-pyroglutamic acid (pGlu) residue, has been synthesized and fully characterized by H-1 and C-13 NMR. The effects of replacing pGlu with its sulphonamido counterpart on biological activity have been investigated. This peptide, which is significantly stabilized towards hydrolysis by pyroglutamyl peptidase type I (PP I, EC 3.4.19.3), has shown to maintain in vitro prolactin-releasing activity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01232-6