(tert-butyloxycarbonyl)-L-leucyl-β-benzyl-L-aspartic acid phenethyl ester | 103934-29-8

• 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: (tert-butyloxycarbonyl)-L-leucyl-β-benzyl-L-aspartic acid phenethyl ester
• 英文别名: 4-O-benzyl 1-O-(2-phenylethyl) (2S)-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]butanedioate
• CAS: 103934-29-8
• 化学式: C₃₀H₄₀N₂O₇
• 分子量: 540.657
• InChiKey: DQTNZZLLMFXAEK-DQEYMECFSA-N

物化性质

• 沸点：
  695.3±55.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (tert-butyloxycarbonyl)-L-leucyl-β-benzyl-L-aspartic acid phenethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 Boc-Leu-Asp phenethyl 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phenethyl ester derivative analogues of the C-terminal tetrapeptide of gastrin, in which the phenylalanyl residue has been replaced by a phenethyl group and the peptide bond between aspartic acid and phenylalanine by an ester bond, were synthesized.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：

  4-O-benzyl 1-O-(2-phenylethyl) (2S)-2-aminobutanedioate;2,2,2-trifluoroacetic acid 、 BOC-L-亮氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (tert-butyloxycarbonyl)-L-leucyl-β-benzyl-L-aspartic acid phenethyl 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phenethyl ester derivative analogues of the C-terminal tetrapeptide of gastrin, in which the phenylalanyl residue has been replaced by a phenethyl group and the peptide bond between aspartic acid and phenylalanine by an ester bond, were synthesized.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

文献信息

• ——
  作者：MARTINEZ J.、 BALI J. -P.、 MAGOUS R.、 CASTRO B.、 DEMAME H.

  DOI：——

  日期：——