glycyl-(D,L)-5,5-dimethylprolyl-L-glutamic acid | 853400-77-8

• 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: glycyl-(D,L)-5,5-dimethylprolyl-L-glutamic acid
• 英文别名: H-Gly-dmP-Glu-OH；(2S)-2-[[(2S)-1-(2-aminoacetyl)-5,5-dimethylpyrrolidine-2-carbonyl]amino]pentanedioic acid
• CAS: 853400-77-8
• 化学式: C₁₄H₂₃N₃O₆
• 分子量: 329.353
• InChiKey: KNUZCBVWBGSPRA-IUCAKERBSA-N

物化性质

• 沸点：
  646.3±55.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  5,5-二甲基脯氨酸 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 (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 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 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

文献信息

• Analogs of Glycyl-Prolyl-Glutamate
  申请人：Brimble Margaret Anne

  公开号：US20080145335A1

  公开（公告）日：2008-06-19

  Embodiments of this invention include novel analogs of Glycyl-Prolyl-Glutamate (GPE) and compositions containing such analogs of GPE. Of these, certain analogs have modified proline residues. Other embodiments of this invention include uses of analogs of GPE to protect neural cells from degeneration and/or death in response to injury or disease. Disorders treatable with compounds and compositions of this invention include hypoxia/ischemia, toxic injury, and chronic neurodegenerative disorders including Parkinson's disease.

  本发明的实施例包括甘氨酰-脯氨酰-谷氨酸（GPE）的新型类似物和含有这种类似物的组合物。其中，某些类似物具有改性脯氨酸残基。本发明的其他实施例包括使用GPE的类似物保护神经细胞免受损伤或疾病引起的退化和/或死亡。可用本发明的化合物和组合物治疗的疾病包括缺氧/缺血、毒性损伤和慢性神经退行性疾病，包括帕金森病。
• 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.
• ANALOGS OF GLYCYL-PROLYL-GLUTAMATE
  申请人：Neuren Pharmaceuticals Limited

  公开号：EP1888618A2

  公开（公告）日：2008-02-20
• EP1888618A4
  申请人：——

  公开号：EP1888618A4

  公开（公告）日：2009-07-15
• US7863304B2
  申请人：——

  公开号：US7863304B2

  公开（公告）日：2011-01-04