L-亮氨酸,N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]-3-(1H-吲哚-3-基)丙基]-,(S)- | 103934-58-3

• 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
• 中文名称: L-亮氨酸,N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]-3-(1H-吲哚-3-基)丙基]-,(S)-
• 英文名称: (tert-butyloxycarbonyl)-L-tryptophyl-ψ(CH2NH)-L-leucine
• CAS: 103934-58-3
• 化学式: C₂₂H₃₃N₃O₄
• 分子量: 403.522
• InChiKey: BKXCRYCGFLOGOJ-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103.45
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  L-亮氨酸,N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]-3-(1H-吲哚-3-基)丙基]-,(S)- 在 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Boc-Trp-ψ(CH2NH)-Leu-Asp p-fluorophenethyl ester
  参考文献：
  名称：

  Phenethyl ester derivative analogs of the C-terminal tetrapeptide of gastrin as potent gastrin antagonists

  摘要：

  A series of phenethyl ester derivative analogues of the C-terminal tetrapeptide of gastrin, in which the phenylalanyl residue has been replaced by a phenethyl group and the peptide bond between aspartic acid and phenylalanine by an ester bond, were synthesized. None of these derivatives were able to stimulate gastric acid secretion in the anesthetized rat, whereas they inhibited gastrin-induced acid secretion with ED50 values between 0.02 and 1.5 mg/kg. Among these derivatives, Boc-beta Ala-Trp-Leu-Asp phenethyl ester (9) and Boc-beta Ala-Trp-Leu-Asp p-fluorophenethyl ester (16) were very potent in inhibiting gastrin-induced acid secretion. From these studies, the significant role of the C-terminal dipeptide of gastrin was pointed out. More particularly, the functional role of the phenylalanine through the C-terminal carboxamide and its binding role through its aromatic ring were demonstrated.

  DOI：

  10.1021/jm00161a012
• 作为产物：
  描述：

  乙酰赖氨酸 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 L-亮氨酸,N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]-3-(1H-吲哚-3-基)丙基]-,(S)-
  参考文献：
  名称：

  Phenethyl ester derivative analogs of the C-terminal tetrapeptide of gastrin as potent gastrin antagonists

  摘要：

  A series of phenethyl ester derivative analogues of the C-terminal tetrapeptide of gastrin, in which the phenylalanyl residue has been replaced by a phenethyl group and the peptide bond between aspartic acid and phenylalanine by an ester bond, were synthesized. None of these derivatives were able to stimulate gastric acid secretion in the anesthetized rat, whereas they inhibited gastrin-induced acid secretion with ED50 values between 0.02 and 1.5 mg/kg. Among these derivatives, Boc-beta Ala-Trp-Leu-Asp phenethyl ester (9) and Boc-beta Ala-Trp-Leu-Asp p-fluorophenethyl ester (16) were very potent in inhibiting gastrin-induced acid secretion. From these studies, the significant role of the C-terminal dipeptide of gastrin was pointed out. More particularly, the functional role of the phenylalanine through the C-terminal carboxamide and its binding role through its aromatic ring were demonstrated.

  DOI：

  10.1021/jm00161a012