Carbonic acid 4-((S)-2-tert-butoxycarbonylamino-2-{(R)-1-{[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-4-[((S)-pyrrolidine-2-carbonyl)-amino]-butylcarbamoyl}-ethyl)-phenyl ester tert-butyl ester | 1053257-97-8

• 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: Carbonic acid 4-((S)-2-tert-butoxycarbonylamino-2-{(R)-1-{[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-4-[((S)-pyrrolidine-2-carbonyl)-amino]-butylcarbamoyl}-ethyl)-phenyl ester tert-butyl ester
• 英文别名: Boc-Tyr(Boc)(Boc)-D-Orn(1)-Gly-Phe-NH2.H-Pro-(1)；[4-[(2S)-3-[[(2R)-1-[[2-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-5-[[(2S)-pyrrolidine-2-carbonyl]amino]pentan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenyl] tert-butyl carbonate
• CAS: 1053257-97-8
• 化学式: C₄₀H₅₇N₇O₁₀
• 分子量: 795.933
• InChiKey: SDWFJHIBRLBTQG-JVVMDBNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  57
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  245
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Carbonic acid 4-((S)-2-tert-butoxycarbonylamino-2-{(R)-1-{[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-4-[((S)-pyrrolidine-2-carbonyl)-amino]-butylcarbamoyl}-ethyl)-phenyl ester tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-Pyrrolidine-2-carboxylic acid ((R)-4-[(S)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-4-{[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-butyl)-amide
  参考文献：
  名称：

  Synthesis and biological activity of branched enkephalin analogues

  摘要：

  The synthesis and biological activity of a new type of enkephalin analogs are reported. A series of branched penta peptides of the enkephalin sequence with replacement of 2-glycine by D-ornithine and branching of the peptide chain in position 2 by attachment of proline, leucine, asparagine or methionine residues to the delta-amino group of D-ornithine were synthesized by classical solution methodology. Analgesic activity of the new analogs was assayed by the 'tail pinch' method following intracisternal and intravenous administrations to mice. They showed higher analgesic potency and longer duration of action as compared to linear and cyclic pentapeptides with the same amino acid composition. The activity determined in the GPI and MVD bioassays, and in a binding assay, revealed the preference of the branched analogs for the mu-type of opioid receptor over the delta-type. These results raise the possibility to synthesize enkephalin analogs with high analgesic potency and opiate receptor selectivity by varying the chemical character and length of the side chain in the 2-position. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80060-3
• 作为产物：
  描述：

  Boc-Tyr(Boc)(Boc)-D-Orn-Gly-Phe-OH 在 钯 1-hydroxy-1H-benzotriazole ammonium salt 、 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 Carbonic acid 4-((S)-2-tert-butoxycarbonylamino-2-{(R)-1-{[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-4-[((S)-pyrrolidine-2-carbonyl)-amino]-butylcarbamoyl}-ethyl)-phenyl ester tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological activity of branched enkephalin analogues

  摘要：

  The synthesis and biological activity of a new type of enkephalin analogs are reported. A series of branched penta peptides of the enkephalin sequence with replacement of 2-glycine by D-ornithine and branching of the peptide chain in position 2 by attachment of proline, leucine, asparagine or methionine residues to the delta-amino group of D-ornithine were synthesized by classical solution methodology. Analgesic activity of the new analogs was assayed by the 'tail pinch' method following intracisternal and intravenous administrations to mice. They showed higher analgesic potency and longer duration of action as compared to linear and cyclic pentapeptides with the same amino acid composition. The activity determined in the GPI and MVD bioassays, and in a binding assay, revealed the preference of the branched analogs for the mu-type of opioid receptor over the delta-type. These results raise the possibility to synthesize enkephalin analogs with high analgesic potency and opiate receptor selectivity by varying the chemical character and length of the side chain in the 2-position. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80060-3