Arg-Pro-Gly-Leu-Leu-Asp-Leu-Lys

• 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: Arg-Pro-Gly-Leu-Leu-Asp-Leu-Lys
• 英文别名: Octaneuropeptide；(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-4-methylpentanoyl]amino]hexanoic acid
• 化学式: C₄₁H₇₄N₁₂O₁₁
• 分子量: 911.112
• InChiKey: ZMHOWEUHDSPZTF-XIJWKTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  64
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  386
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  Fmoc-L-亮氨酸 、 Fmoc-L-脯氨酸 、 Fmoc-L-天冬氨酸 beta-叔丁酯 、 聚甘氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 Arg-Pro-Gly-Leu-Leu-Asp-Leu-Lys
  参考文献：
  名称：

  Structure−Activity Relationships of a Series of Analogues of the Octadecaneuropeptide ODN on Calcium Mobilization in Rat Astrocytes

  摘要：

  The octadecaneuropeptide ODN (QATVGDVNTDRPGLLDLK)I originally characterized as an endogenous ligand for central-type benzodiazepine receptors, increases intracellular calcium concentration ([Ca2+](i)) in rat astroglial cells. A series of ODN analogues was synthesized, and each compound was studied for its ability to induce Ca2+ mobilization in cultured rat astrocytes. Replacement of each amino acid by an L-alanine residue (AlaScan) showed that the N-terminal region of the molecule was relatively tolerant to alanine substitution (2-8, 10), except for the Ala(9)-substituted analogue (9) which was totally devoid of activity. Pyroglutamization (21) and acetylation (22) of the GLn(1) residue reduced the Ca2+ response suggesting that a free N-terminal amine function is required for full activity of ODN. Alanine substitution of the residues in the C-terminal region of the molecule (11-14, 16-18) significantly reduced the biological activity of ODN. In particular, modifications of the Leu(15) residue (15, 20) abolished the Ca2+-mobilizing activity. The analogues [Ala(9)]ODN (9), [Ala(15)]ODN(15), [D-Thr(9)]ODN (19), and [D-Leu(15)]ODN (20) partially antagonized the Ca2+ response evoked by ODN. Most importantly, the octapeptide ODN11-18 (OP, 24) produced a dose-response curve that was superimposable to that obtained with ODN, indicating that the C-terminal region of the molecule possesses full biological activity. Finally, the AlaScan of OP revealed that replacement of the Leu(5) residue by Ala (29) or D-Leu (33) totally suppressed the calcium response, confirming the crucial contribution of the Leu(15) residue of ODN to the biological activity of the neuropeptide.

  DOI：

  10.1021/jm980275d