(tert-butyloxycarbonyl)-L-tryptophyl-ψ(CH2-NH)-L-leucyl-β-benzyl-L-aspartyl-L-phenylalanine amide | 97530-06-8

• 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-tryptophyl-ψ(CH2-NH)-L-leucyl-β-benzyl-L-aspartyl-L-phenylalanine amide
• CAS: 97530-06-8
• 化学式: C₄₂H₅₄N₆O₇
• 分子量: 754.927
• InChiKey: DISZVENVCBHXLC-SNZVYYTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  55.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  193.74
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (tert-butyloxycarbonyl)-L-tryptophyl-ψ(CH2-NH)-L-leucyl-β-benzyl-L-aspartyl-L-phenylalanine amide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以91%的产率得到(tert-butyloxycarbonyl)-L-tryptophyl-ψ(CH2-NH)-L-leucyl-L-aspartyl-L-phenylalanine amide
  参考文献：
  名称：

  Synthesis and biological activities of some pseudo-peptide analogs of tetragastrin: the importance of the peptide backbone

  摘要：

  Pseudo-peptide analogues of the C-terminal tetrapeptide of gastrin, in which a peptide bond has been replaced by a CH2-NH bond, i.e. (tert-butyloxycarbonyl)-L-tryptophyl-psi (CH2-NH)-L-leucyl-L-aspartyl-L-phenylalanine amide (8), (tert-butyloxycarbonyl)-L-tryptophyl-L-leucyl-psi (CH2-NH)-L-aspartyl-L-phenylalanine amide (13), (tert-butyloxycarbonyl)-L-tryptophyl-L-leucyl-L-aspartyl-psi (CH2NH)-L-phenylalanine amide (20), were synthesized. The pseudo-peptides 8 and 13 were shown to have the same affinity as (tert-butyloxycarbonyl)-L-tryptophyl-L-leucyl-L-aspartyl-L-phenylalanine amide (21) for the gastrin receptor on isolated mucosal cells. The pseudo-peptide 20 exhibited lower affinity (IC50 congruent to 10(-5) M). The biological activity of these pseudo-peptides was studied on acid secretion in the anesthetized rat. Compound 8 stimulated acid secretion, identically with that of 21. Compound 13 did not exhibit any agonist activity but was able to antagonize the action of gastrin (ED50 = 0.3 mg/kg). Compound 20 did not show any agonist activity but was able to inhibit gastrin-induced acid secretion, with lower potency (ED50 = 15 mg/kg). The importance of the peptide bonds in the mode of action of gastrin is discussed, and a hypothetical approach of the mechanism of action is presented.

  DOI：

  10.1021/jm00150a020
• 作为产物：
  描述：

  (tert-butyloxycarbonyl)-L-leucyl-β-benzyl-L-aspartyl-L-phenylalanine amide 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 (tert-butyloxycarbonyl)-L-tryptophyl-ψ(CH2-NH)-L-leucyl-β-benzyl-L-aspartyl-L-phenylalanine amide
  参考文献：
  名称：

  Synthesis and biological activities of some pseudo-peptide analogs of tetragastrin: the importance of the peptide backbone

  摘要：

  Pseudo-peptide analogues of the C-terminal tetrapeptide of gastrin, in which a peptide bond has been replaced by a CH2-NH bond, i.e. (tert-butyloxycarbonyl)-L-tryptophyl-psi (CH2-NH)-L-leucyl-L-aspartyl-L-phenylalanine amide (8), (tert-butyloxycarbonyl)-L-tryptophyl-L-leucyl-psi (CH2-NH)-L-aspartyl-L-phenylalanine amide (13), (tert-butyloxycarbonyl)-L-tryptophyl-L-leucyl-L-aspartyl-psi (CH2NH)-L-phenylalanine amide (20), were synthesized. The pseudo-peptides 8 and 13 were shown to have the same affinity as (tert-butyloxycarbonyl)-L-tryptophyl-L-leucyl-L-aspartyl-L-phenylalanine amide (21) for the gastrin receptor on isolated mucosal cells. The pseudo-peptide 20 exhibited lower affinity (IC50 congruent to 10(-5) M). The biological activity of these pseudo-peptides was studied on acid secretion in the anesthetized rat. Compound 8 stimulated acid secretion, identically with that of 21. Compound 13 did not exhibit any agonist activity but was able to antagonize the action of gastrin (ED50 = 0.3 mg/kg). Compound 20 did not show any agonist activity but was able to inhibit gastrin-induced acid secretion, with lower potency (ED50 = 15 mg/kg). The importance of the peptide bonds in the mode of action of gastrin is discussed, and a hypothetical approach of the mechanism of action is presented.

  DOI：

  10.1021/jm00150a020