His-Phe-Pro-Gly-Pro

• 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: His-Phe-Pro-Gly-Pro
• 英文别名: (2S)-1-[2-[[(2S)-1-[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carboxylic acid
• 化学式: C₂₇H₃₅N₇O₆
• 分子量: 553.618
• InChiKey: SWNRUSHLSIAVNM-CMOCDZPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  191
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  脯氨酰-甘氨酰-脯氨酰-肾上腺皮质激素 (4-7) 在 pig kidney microsomal aminopeptidase M 作用下， 生成 L-蛋氨酰-L-谷氨酸 、 His-Phe-Pro-Gly-Pro
  参考文献：
  名称：

  Studies of the aminopeptidase proteolysis of semax analogues with different N-terminal amino acid residues

  摘要：

  Proteolysis of semax (Met-Glu-His-Phe-Pro-Gly-Pro, Sem) and its analogues with the substitution of Ala, Gly, Thr, or Trp for the N-terminal Met was studied. This substitution was shown to change the degradation rate of these peptides by leucine aminopeptidase (EC 3.4.11.2, Sigma, Type VI, 9.2 activity units/mg). [Ala(1)] Sem, [Gly(1)] Sem, and [Thr(1)] Sem (the semax analogues) proved to be more stable to the proteolysis than semax itself. It was demonstrated that the primary product of the proteolysis was His-Phe-Pro-Gly-Pro (Sem-5). In the case of [Trp(1)] Sem, the comparable amount of Glu-His-Phe-Pro-Gly-Pro (Sem-6) was found to be formed along with Sem-5. In was established that all the studied semax analogues could be used as inhibitors of its proteolysis.

  DOI：

  10.1134/s1068162011040133

文献信息

• Studies of the aminopeptidase proteolysis of semax analogues with different N-terminal amino acid residues
  作者：K. V. Shevchenko、T. V. V’yunova、I. Yu. Nagaev、L. A. Andreeva、L. Yu. Alfeeva、N. F. Myasoedov

  DOI：10.1134/s1068162011040133

  日期：2011.7

  Proteolysis of semax (Met-Glu-His-Phe-Pro-Gly-Pro, Sem) and its analogues with the substitution of Ala, Gly, Thr, or Trp for the N-terminal Met was studied. This substitution was shown to change the degradation rate of these peptides by leucine aminopeptidase (EC 3.4.11.2, Sigma, Type VI, 9.2 activity units/mg). [Ala(1)] Sem, [Gly(1)] Sem, and [Thr(1)] Sem (the semax analogues) proved to be more stable to the proteolysis than semax itself. It was demonstrated that the primary product of the proteolysis was His-Phe-Pro-Gly-Pro (Sem-5). In the case of [Trp(1)] Sem, the comparable amount of Glu-His-Phe-Pro-Gly-Pro (Sem-6) was found to be formed along with Sem-5. In was established that all the studied semax analogues could be used as inhibitors of its proteolysis.