H-His-Phe-Arg-Trp-Gly-Ala-Pro-Val-NH2

• 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: H-His-Phe-Arg-Trp-Gly-Ala-Pro-Val-NH2
• 英文别名: (2S)-1-[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-phenyl-propanoyl]amino]-5-guanidino-pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]propanoyl]-N-[(1S)-1-carbamoyl-2-methyl-propyl]pyrrolidine-2-carboxamide；(2S)-1-[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-phenylpropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]propanoyl]-N-[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]pyrrolidine-2-carboxamide
• 化学式: C₄₇H₆₅N₁₅O₈
• 分子量: 968.129
• InChiKey: BCGXMZLPSCDQOP-JNZLLMNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  373
• 氢给体数：
  12
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 、 N-Fmoc-N'-三苯甲基-L-组氨酸 、 Fmoc-Pbf-L-精氨酸 、 Fmoc-L-色氨酸(Boc)-OH 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 H-His-Phe-Arg-Trp-Gly-Ala-Pro-Val-NH2
  参考文献：
  名称：

  Novel α-Melanocyte Stimulating Hormone Peptide Analogues with High Candidacidal Activity

  摘要：

  alpha-Melanocyte stimulating hormone (alpha-MSH) is an endogenous linear tridecapeptide with potent antiinflammatory effects. We recently demonstrated that alpha-MSH and its C-terminal sequence Lys-Pro-Val (alpha-MSH (11- 13)) have antimicrobial effects against two major and representative pathogens: Staphylococcus aureus and Candida albicans. In an attempt to improve the candidacidal activity of alpha-MSH and to better understand the peptide structure - antifungal activity relations, we designed and synthesized novel peptide analogues. Because previous data suggested that antimicrobial effects of alpha-MSH were receptor-mediated, we chose to focus on the sequence alpha-MSH (6-13), which contains the invariant core sequence His-Phe-Arg-Trp (6-9) that is important for binding to the known melanocortin receptors and also contains the sequence Lys-Pro-Val (11-13) that is known to be important for antimicrobial activity. In this structure-activity study, we discovered several compounds that have greater candidacidal activity than (alpha-MSH. The peptide [D-Nal-7,Phe-12]-alpha-MSH (6-13) was the most potent of the analogues tested. The present results are very encouraging because they show the great potential of these peptides as a truly novel class of candidacidal compounds.

  DOI：

  10.1021/jm0204338

文献信息

• Novel α-Melanocyte Stimulating Hormone Peptide Analogues with High Candidacidal Activity
  作者：Paolo Grieco、Claudia Rossi、Gualtiero Colombo、Stefano Gatti、Ettore Novellino、James M. Lipton、Anna Catania

  DOI：10.1021/jm0204338

  日期：2003.2.1

  alpha-Melanocyte stimulating hormone (alpha-MSH) is an endogenous linear tridecapeptide with potent antiinflammatory effects. We recently demonstrated that alpha-MSH and its C-terminal sequence Lys-Pro-Val (alpha-MSH (11- 13)) have antimicrobial effects against two major and representative pathogens: Staphylococcus aureus and Candida albicans. In an attempt to improve the candidacidal activity of alpha-MSH and to better understand the peptide structure - antifungal activity relations, we designed and synthesized novel peptide analogues. Because previous data suggested that antimicrobial effects of alpha-MSH were receptor-mediated, we chose to focus on the sequence alpha-MSH (6-13), which contains the invariant core sequence His-Phe-Arg-Trp (6-9) that is important for binding to the known melanocortin receptors and also contains the sequence Lys-Pro-Val (11-13) that is known to be important for antimicrobial activity. In this structure-activity study, we discovered several compounds that have greater candidacidal activity than (alpha-MSH. The peptide [D-Nal-7,Phe-12]-alpha-MSH (6-13) was the most potent of the analogues tested. The present results are very encouraging because they show the great potential of these peptides as a truly novel class of candidacidal compounds.