dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate | 841233-89-4

• 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: dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate
• CAS: 841233-89-4
• 化学式: C₃₄H₃₇N₃O₈
• 分子量: 615.683
• InChiKey: YVVXFEJXWXNNIM-WDYNHAJCSA-N

物化性质

• 沸点：
  828.6±65.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  140.34
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 以94%的产率得到N-(N-glycyl-L-prolyl)-D-glutamic acid
  参考文献：
  名称：

  Synthesis and neuroprotective activity of analogues of glycyl-l-prolyl-l-glutamic acid (GPE) modified at the α-carboxylic acid

  摘要：

  The synthesis of nine GPE* analogues, wherein the alpha-carboxylic acid group of glutamic acid has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline 2 with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.005
• 作为产物：
  描述：

  L-脯氨酸 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 58.67h， 生成 dibenzyl N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-D-glutamate
  参考文献：
  名称：

  Synthesis and neuroprotective activity of analogues of glycyl-l-prolyl-l-glutamic acid (GPE) modified at the α-carboxylic acid

  摘要：

  The synthesis of nine GPE* analogues, wherein the alpha-carboxylic acid group of glutamic acid has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline 2 with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.005

文献信息

• Analogues of the neuroprotective tripeptide Gly-Pro-Glu (GPE): synthesis and structure–activity relationships
  作者：Sergio A. Alonso De Diego、Pilar Muñoz、Rosario González-Muñiz、Rosario Herranz、Mercedes Martín-Martínez、Edurne Cenarruzabeitia、Diana Frechilla、Joaquín Del Río、M. Luisa Jimeno、M. Teresa García-López

  DOI：10.1016/j.bmcl.2005.03.015

  日期：2005.5

  A series of GPE analogues, including modifications at the Pro and/or Glu residues, was prepared and evaluated for their NMDA binding and neuroprotective effects. Main results suggest that the pyrrolidine ring puckering of the Pro residue plays a key role in the biological responses, while the preference for cis or trans rotamers around the Gly-Pro peptide bond is not important. (c) 2005 Elsevier Ltd. All rights reserved.