(S)-1-((2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid | 62023-67-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-1-((2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid
• 英文别名: 1-[(2S,3R)-3-Amino-2-hydroxy-1-oxo-4-phenylbutyl]-L-proline；(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxylic acid
• CAS: 62023-67-0
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: KTXOSNPEUDHINY-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乌苯美司侧链 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-1-((2S,3R)-3-Amino-2-hydroxy-4-phenyl-butyryl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Novel 3-amino-2-hydroxy acids containing protease inhibitors. Part 1: Synthesis and kinetic characterization as aminopeptidase P inhibitors

  摘要：

  Novel, potent inhibitors of aminopeptidase P, containing a 3-amino-2-hydroxy acid and a proline ora proline analogues, have been prepared. One part of the bestatin-derived inhibitors was found to inhibit APP from Excherichia coli and from rat intestine according to a mixed-type mechanism, with K-i values up to 1.26 mu M. The other compounds. 3-amino-2-hydroxy acyl prolines of a different configuration. inhibit APP competitively, according to a slow-binding mechanism, with K-i values in the nanomolar up to the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.040

文献信息

• Novel 3-amino-2-hydroxy acids containing protease inhibitors. Part 1: Synthesis and kinetic characterization as aminopeptidase P inhibitors
  作者：Angela Stöckel-Maschek、Beate Stiebitz、Regine Koelsch、Klaus Neubert

  DOI：10.1016/j.bmc.2005.05.040

  日期：2005.8

  Novel, potent inhibitors of aminopeptidase P, containing a 3-amino-2-hydroxy acid and a proline ora proline analogues, have been prepared. One part of the bestatin-derived inhibitors was found to inhibit APP from Excherichia coli and from rat intestine according to a mixed-type mechanism, with K-i values up to 1.26 mu M. The other compounds. 3-amino-2-hydroxy acyl prolines of a different configuration. inhibit APP competitively, according to a slow-binding mechanism, with K-i values in the nanomolar up to the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.