[D-Val12]des-acyl-ghrelin-(6-13) | 1363567-54-7

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: [D-Val12]des-acyl-ghrelin-(6-13)
• 英文别名: SPEHQRvQ-NH2；H-Ser-Pro-Glu-His-Gln-Arg-D-Val-Gln-NH2；(4S)-5-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2R)-1-[[(2S)-1,5-diamino-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-[[(2S)-1-[(2S)-2-amino-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid
• CAS: 1363567-54-7
• 化学式: C₄₀H₆₆N₁₆O₁₃
• 分子量: 979.063
• InChiKey: GPMRZQBDQVMUOW-KVGVFPRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.5
• 重原子数：
  69
• 可旋转键数：
  31
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  501
• 氢给体数：
  15
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2,6-bis(N-trimellitimido)-4-trifluoromethyl-40-phenoxydiphenyl ether 在 茴香硫醚 、 水 、 1,2-乙二硫醇 、 三氟乙酸 、 苯酚 作用下， 反应 3.0h， 生成 [D-Val12]des-acyl-ghrelin-(6-13)
  参考文献：
  名称：

  Des-Acyl Ghrelin Fragments and Analogues Promote Survival of Pancreatic β-Cells and Human Pancreatic Islets and Prevent Diabetes in Streptozotocin-Treated Rats

  摘要：

  Des-acyl ghrelin, although devoid of binding to ghrelin receptor (GRLN), exerts many biological effects, including regulation of glucose and lipid metabolism. Indeed, des-acyl ghrelin promotes pancreatic beta-cell and human islet cell survival and prevents diabetes in streptozotocin (STZ) treated rats. We investigated whether des-acyl ghrelin fragments excluding serine(3), which is essential for binding to GRLN, would display similar actions. Among the different compounds tested, des-acyl ghrelin((6-13)) and des-acyl ghrelin((6-13)) with alanine substitutions or cyclization, but not with D-amino acid substitutions, showed the best survival effect, similar to des-acyl ghrelin. Des-acyl ghrelin((6-13)) even prevented diabetes in STZ-treated rats and protected human circulating angiogenic cells from oxidative stress and senescence, similar to des-acyl ghrelin. These results suggest that not only full-length des-acyl ghrelin but also short des-acyl ghrelin fragments have clear beneficial effects on several tissues in vitro and in vivo.

  DOI：

  10.1021/jm201223m