(S)-2-{[(S)-1-(2-Benzyloxycarbonylamino-acetyl)-5,5-dimethyl-pyrrolidine-2-carbonyl]-amino}-pentanedioic acid dibenzyl ester | 900159-01-5

• 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)-2-{[(S)-1-(2-Benzyloxycarbonylamino-acetyl)-5,5-dimethyl-pyrrolidine-2-carbonyl]-amino}-pentanedioic acid dibenzyl ester
• CAS: 900159-01-5
• 化学式: C₃₆H₄₁N₃O₈
• 分子量: 643.737
• InChiKey: YLNXZOKKKCFPGO-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (S)-2-{[(S)-1-(2-Benzyloxycarbonylamino-acetyl)-5,5-dimethyl-pyrrolidine-2-carbonyl]-amino}-pentanedioic acid dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 6.0h， 以100%的产率得到glycyl-(D,L)-5,5-dimethylprolyl-L-glutamic acid
  参考文献：
  名称：

  The neuroprotective activity of GPE tripeptide analogues does not correlate with glutamate receptor binding affinity

  摘要：

  The influence of several modifications on the GPE tripeptide structure upon the binding to GluRs and on their neuroprotective effects has been studied. The results indicated that the prevention of neuronal death showed by GPE and some analogues is not directly related to their affinity at glutamate receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.033
• 作为产物：
  描述：

  5,5-二甲基脯氨酸 在 盐酸 、 4-二甲氨基吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 (S)-2-{[(S)-1-(2-Benzyloxycarbonylamino-acetyl)-5,5-dimethyl-pyrrolidine-2-carbonyl]-amino}-pentanedioic acid dibenzyl ester
  参考文献：
  名称：

  The neuroprotective activity of GPE tripeptide analogues does not correlate with glutamate receptor binding affinity

  摘要：

  The influence of several modifications on the GPE tripeptide structure upon the binding to GluRs and on their neuroprotective effects has been studied. The results indicated that the prevention of neuronal death showed by GPE and some analogues is not directly related to their affinity at glutamate receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.033

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.