N-(benzyloxycarbonyl)-O-tert-butyltyrosylglycylglycine ethyl ester | 107941-81-1

• 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: N-(benzyloxycarbonyl)-O-tert-butyltyrosylglycylglycine ethyl ester
• 英文别名: Z-L-Tyr(Bu-t)-Gly-Gly-OEt
• CAS: 107941-81-1
• 化学式: C₂₇H₃₅N₃O₇
• 分子量: 513.591
• InChiKey: KXYIZGQDKGZDHC-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  132.06
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-O-tert-butyltyrosylglycylglycine ethyl ester 在 palladium on activated charcoal N-甲基吗啉 、 sodium hydroxide 、 氢气 、 ammonium formate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.17h， 生成 (N,N-dipropyl,Leu⁵)enkephalin
  参考文献：
  名称：

  N,N-Dialkylated leucine enkephalins as potential .delta. opioid receptor antagonists

  摘要：

  A series of N,N-dialkylated leucine enkephalins were prepared in order to study the effect of substitution on antagonist activity at the delta opioid receptor. The target peptides 1-7 were evaluated in the mouse vas deferens (MVD) and guinea pig ileum (GPI) at 1 microM. All of the compounds except [N,N-di-2-phenethyl,Leu5]enkephalin (7) showed antagonist activity in the MVD against the delta receptor agonist [D-Ala2,D-Leu5]enkephalin. The most potent congener, [N,N-dibenzyl,Leu5]enkephalin (3), was 2.5-fold more potent than [N,N-diallyl,Leu5]enkephalin (1). None of the compounds at 1 microM showed any antagonist activity against agonists for other receptor types. The N,N-di-2-phenethyl (7) and N,N-dioctyl (6) analogues showed significant agonist activity at 1 microM in the MVD.

  DOI：

  10.1021/jm00390a005
• 作为产物：
  描述：

  N-[(苯基甲氧基)羰基]-L-酪氨酸乙酯 在 N-甲基吗啉 、 sodium hydroxide 、 硫酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(benzyloxycarbonyl)-O-tert-butyltyrosylglycylglycine ethyl ester
  参考文献：
  名称：

  N,N-Dialkylated leucine enkephalins as potential .delta. opioid receptor antagonists

  摘要：

  A series of N,N-dialkylated leucine enkephalins were prepared in order to study the effect of substitution on antagonist activity at the delta opioid receptor. The target peptides 1-7 were evaluated in the mouse vas deferens (MVD) and guinea pig ileum (GPI) at 1 microM. All of the compounds except [N,N-di-2-phenethyl,Leu5]enkephalin (7) showed antagonist activity in the MVD against the delta receptor agonist [D-Ala2,D-Leu5]enkephalin. The most potent congener, [N,N-dibenzyl,Leu5]enkephalin (3), was 2.5-fold more potent than [N,N-diallyl,Leu5]enkephalin (1). None of the compounds at 1 microM showed any antagonist activity against agonists for other receptor types. The N,N-di-2-phenethyl (7) and N,N-dioctyl (6) analogues showed significant agonist activity at 1 microM in the MVD.

  DOI：

  10.1021/jm00390a005

文献信息

• A Simple and Convenient Method for the Synthesis of Iminomethylene Analogs of Peptides
  作者：Hidekazu Oyamada、Masaaki Ueki

  DOI：10.1246/bcsj.60.267

  日期：1987.1

  improving the conditions for the selective reduction of the peptide bond of N-protected dipeptide esters by borane. Among the ester residues investigated, the t-butyl ester gave the best result. During reactions no racemization occurred. [L-Pheψ[CH2–NH]L-Leu4−5]leucineenkephalin was synthesized in good yield starting from N-benzyloxycarbonyl-L-phenylalanyl-L-leucine t-butyl ester.

  研究了合成部分肽键被其他等排键取代的假肽，以获得长效肽药物，并研究肽与生物活性的构效关系。通过改进硼烷选择性还原 N 保护的二肽酯的肽键的条件，建立了一种简单方便的合成假 [CH2–NH]肽的方法。在所研究的酯残基中，叔丁酯的结果最好。在反应过程中没有发生外消旋化。[L-Pheψ[CH2-NH]L-Leu4-5]亮氨酸脑啡肽以N-苄氧羰基-L-苯丙氨酰基-L-亮氨酸叔丁酯为原料，以良好的收率合成。