苄氧羰基-甘氨酰-脯氨酰-琥珀酰亚胺 | 38417-02-6

• 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
• 中文名称: 苄氧羰基-甘氨酰-脯氨酰-琥珀酰亚胺
• 中文别名: N-苄氧羰基-甘氨酰脯氨酸-N-羟基琥珀酰亚胺酯
• 英文名称: N-(N-benzyloxycarbonyl-glycyl)-L-proline N-hydroxysuccinimidyl ester
• 英文别名: Z-Gly-pro-osu；(2,5-dioxopyrrolidin-1-yl) (2S)-1-[2-(phenylmethoxycarbonylamino)acetyl]pyrrolidine-2-carboxylate
• CAS: 38417-02-6
• 化学式: C₁₉H₂₁N₃O₇
• 分子量: 403.392
• InChiKey: YOEIDHODHKSHNL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄氧羰基-甘氨酰-脯氨酰-琥珀酰亚胺 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 以85%的产率得到[2-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  A chemical model for the activation of pyruvate-formate-lyase

  摘要：

  A chemical model is described for the activation of the carbon-centred radical-based enzyme, pyruvate-formate-lyase. The feasibility of a 5'-deoxyadenosyl radical abstracting a hydrogen atom from C-2 of a peptideglycine residue has been demonstrated in an intramolecular process.

  DOI：

  10.1016/0040-4039(95)00167-b
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 苄氧羰基-甘氨酰-脯氨酰-琥珀酰亚胺
  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

• Copper-Catalyzed [3 + 2] Cycloaddition Reaction of <i>N</i>-Hydroxysuccinimide Ester with Isocyanoacetates for the Synthesis of 4,5-Disubstituted Oxazoles
  作者：Shuo Wang、Shi-Jie Ma、Ji-Cong Lou、Wen-Wu Sun、Bin Wu

  DOI：10.1021/acs.joc.2c03084

  日期：——

  The cycloaddition reaction of N-hydroxysuccinimide ester and isocyanatoacetate catalyzed by copper was described. A series of 4,5-disubstituted oxazole compounds, including ones derived from natural fatty acids, drugs, amino acids, and peptides, were obtained in moderate to high yields. The derivatization reaction was explored. The reaction mechanism was discussed.

  描述了铜催化的N-羟基琥珀酰亚胺酯与异氰酸根乙酸酯的环加成反应。以中高产率获得了一系列 4,5-二取代恶唑化合物，包括衍生自天然脂肪酸、药物、氨基酸和肽的化合物。探索了衍生化反应。讨论了反应机理。
• The Study of Stability of Proline-Containing Derivatives of Dopamine and Serotonin in the Biological Media in Vitro Experiments
  作者：K. V. Shevchenko、L. A. Andreeva、I. Yu. Nagaev、V. P. Shevchenko、N. F. Myasoedov

  DOI：10.1134/s1990750820020110

  日期：2020.4

  The peptides Boc-Gly-Pro-DP, Z-Gly-Pro-DP, LA-Gly-Pro-DP, Boc-Gly-Pro-Srt, Z-Gly-Pro-Srt have been synthesized for the first time. The study of their stability in the presence of leucine aminopeptidase, carboxypeptidase Y, carboxypeptidase B, and proline endopeptidase (PEP) has shown that the synthesized peptides are stable in the presence of aminopeptidases and carboxypeptidases. In the presence of PEP, dopamine (DP) and serotonin (Srt) have been cleaved from these substances. Thus, the originally synthesized proline derivatives of Srt and DP may be considered as the resources, from which Srt and DP can be gradually released. This creates the possibility of a prolonged action of these biologically active compounds on cells and, consequently, on the whole body.
• Guziec, Frank S.; Wasmund, Loide Mayer, Journal of Chemical Research, Miniprint, 1989, # 6, p. 1301 - 1353
  作者：Guziec, Frank S.、Wasmund, Loide Mayer

  DOI：——

  日期：——
• Chain reversals in model peptides: studies of cystine-containing cyclic peptides. 1. Conformational free energies of cyclization of hexapeptides of sequence Ac-Cys-X-Pro-Gly-Y-Cys-NHMe
  作者：P. J. Milburn、Y. Konishi、Y. C. Meinwald、H. A. Scheraga

  DOI：10.1021/ja00249a010

  日期：1987.7
• Synthesis and pharmacological evaluation of side chain modified glutamic acid analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)
  作者：Margaret A. Brimble、Nicholas S. Trotter、Paul W.R. Harris、Frank Sieg

  DOI：10.1016/j.bmc.2004.10.006

  日期：2005.1

  The synthesis of eight GPE* analogues, wherein the gamma-carboxylic moiety of the glutamic residue has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline 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.