Z-Arg(Z2)-Leu-Leu-Gln-OH | 153097-58-6

• 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
• 英文名称: Z-Arg(Z2)-Leu-Leu-Gln-OH
• CAS: 153097-58-6
• 化学式: C₄₇H₆₂N₈O₁₂
• 分子量: 931.056
• InChiKey: ULCGPPJYQBZPCX-ZQWQDMLBSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  67.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  295.04
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Z-Arg(Z2)-Leu-Leu-Gln-OH 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 hydroxyoxobenzotriazine 、 氢溴酸 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 H-Arg(HBr)-Leu-Leu-Gln-Gly-Leu-Val-NH2
  参考文献：
  名称：

  Zur Totalsynthese von Human-Sekretin

  摘要：

  The synthesis of the heptacosapeptide amide with the primary structure of Human-secretin is described. For this purpose 7 fragments were designed, i.e. H-Gly-Leu-Val-NH2 [25-27b], Z-Arg(Z2)-Leu-Leu-Gln-OH [21-24], Z-Arg(Z2)-Leu-Gln-OH[18-20], Z-Arg(Z2)-Glu(OtBu)-Gly-Ala-OH [14-17], Z-Arg(Z2)-Leu-OH [12-13], Z-Thr(tBu)-Ser(tBu)-Glu(OtBu)-Leu-Ser(tBu)-OH [7-11], Adoc-His(Adoc)-Ser(tBu)-Asp(OtBu)-Gly-Thr(tBu)-Phe-OH [1-6]; these fragments were consequently assembled to the overall protected total sequence using the Wunsch/Weygand-method with dicyclohexylcarbodiimide. After deprotection by exposure to trifluoroacetic acid in presence of 1,2-ethanedithiol and water as scavenger, the isolated crude product was purified by column chromatography on CM-Sepharose, fast flow. This synthetized Human-secretin showed the full biological activity in comparison to Porcine-secretin.

  DOI：

  10.1007/bf00819525
• 作为产物：
  描述：

  L-谷氨酰胺 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 碳酸氢钠 、 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Z-Arg(Z2)-Leu-Leu-Gln-OH
  参考文献：
  名称：

  Zur Totalsynthese von Human-Sekretin

  摘要：

  The synthesis of the heptacosapeptide amide with the primary structure of Human-secretin is described. For this purpose 7 fragments were designed, i.e. H-Gly-Leu-Val-NH2 [25-27b], Z-Arg(Z2)-Leu-Leu-Gln-OH [21-24], Z-Arg(Z2)-Leu-Gln-OH[18-20], Z-Arg(Z2)-Glu(OtBu)-Gly-Ala-OH [14-17], Z-Arg(Z2)-Leu-OH [12-13], Z-Thr(tBu)-Ser(tBu)-Glu(OtBu)-Leu-Ser(tBu)-OH [7-11], Adoc-His(Adoc)-Ser(tBu)-Asp(OtBu)-Gly-Thr(tBu)-Phe-OH [1-6]; these fragments were consequently assembled to the overall protected total sequence using the Wunsch/Weygand-method with dicyclohexylcarbodiimide. After deprotection by exposure to trifluoroacetic acid in presence of 1,2-ethanedithiol and water as scavenger, the isolated crude product was purified by column chromatography on CM-Sepharose, fast flow. This synthetized Human-secretin showed the full biological activity in comparison to Porcine-secretin.

  DOI：

  10.1007/bf00819525