L-alanyl-L-prolyl-L-glutamic acid | 71190-92-6

• 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: L-alanyl-L-prolyl-L-glutamic acid
• 英文别名: Ala-Pro-Glu；(2S)-2-[[(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carbonyl]amino]pentanedioic acid
• CAS: 71190-92-6
• 化学式: C₁₃H₂₁N₃O₆
• 分子量: 315.326
• InChiKey: IORKCNUBHNIMKY-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  dibenzyl N-tert-butoxycarbonyl-L-prolyl-L-glutamate 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 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 43.0h， 生成 L-alanyl-L-prolyl-L-glutamic acid
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of glycine-modified analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)

  摘要：

  The synthesis of 10 G*PE analogues, wherein the glycine residue has been modified, is described by coupling readily accessible dibenzyl-L-prolyl-L-glutamate 2 with various analogues of glycine. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glycine residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.004

文献信息

• New Gly-Pro-Glu (GPE) analogues: Expedite solid-phase synthesis and biological activity
  作者：Sergio A. Alonso De Diego、Marta Gutiérrez-Rodríguez、M. Jesús Pérez de Vega、Diego Casabona、Carlos Cativiela、Rosario González-Muñiz、Rosario Herranz、Edurne Cenarruzabeitia、Diana Frechilla、Joaquín Del Río、M. Luisa Jimeno、M. Teresa García-López

  DOI：10.1016/j.bmcl.2005.11.040

  日期：2006.3

  A suitable solid-phase approach, based on Fmoc/Bu-t methodology and on the use of 2-chlorotrityl resin, allowed a rapid and efficient preparation of new GPE analogues. Most of the synthesized tripeptides displayed glutamate receptor binding affinity comparable to that of GPE, but only a few derivatives showed significant neuroprotective activity. (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacological evaluation of glycine-modified analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)
  作者：Michelle Y.H. Lai、Margaret A. Brimble、David J. Callis、Paul W.R. Harris、Mark S. Levi、Frank Sieg

  DOI：10.1016/j.bmc.2004.10.004

  日期：2005.1

  The synthesis of 10 G*PE analogues, wherein the glycine residue has been modified, is described by coupling readily accessible dibenzyl-L-prolyl-L-glutamate 2 with various analogues of glycine. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glycine residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.