Z-Asn-Val-Val-Gly-OEt | 147424-49-5

• 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: Z-Asn-Val-Val-Gly-OEt
• 英文别名: Cbz-Asn-Val-Val-Gly-OEt；ethyl 2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]acetate
• CAS: 147424-49-5
• 化学式: C₂₆H₃₉N₅O₈
• 分子量: 549.624
• InChiKey: QOTWORAQSJMVHK-NYVOZVTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  195
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Z-Asn-Val-Val-Gly-OEt 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 ((S)-2-{(S)-2-[(S)-2-((S)-2-{(R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-phenyl-propionylamino)-3-carbamoyl-propionylamino]-3-methyl-butyrylamino}-3-methyl-butyrylamino)-acetic acid ethyl ester
  参考文献：
  名称：

  Unique sequence in deltorphin C confers structural requirement for δ opioid receptor selectivity

  摘要：

  A series of deltorphin C (H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues were synthesized to assess the consequences of changing anionic and hydrophobic residues on delta receptor selectivity. Analogues with altered C-terminal groups, inverted sequences, or esterified with tert-butyl, benzyl, or ethyl groups revealed that high delta selectivity required an unmodified amino acid sequence. Shifts of Asp and hydrophobic residues decreased delta selectivity due to loss in delta affinity (5- to almost-equal-to 700-fold); mu affinity was unchanged or increased 14-fold. Suppression of charge or deamidation diminished delta selectivity through reduced delta and modified mu affinities. Data provide evidence that a negative charge does not a priori guarantee high selectivity and specific alignment of anionic and hydrophobic residues might facilitate optimum spatial configuration which complements the 8 receptor binding site.

  DOI：

  10.1016/0223-5234(92)90113-f
• 作为产物：
  描述：

  N-苄氧羰基-L-缬氨酸琥珀酰亚胺酯 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 Z-Asn-Val-Val-Gly-OEt
  参考文献：
  名称：

  Unique sequence in deltorphin C confers structural requirement for δ opioid receptor selectivity

  摘要：

  A series of deltorphin C (H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues were synthesized to assess the consequences of changing anionic and hydrophobic residues on delta receptor selectivity. Analogues with altered C-terminal groups, inverted sequences, or esterified with tert-butyl, benzyl, or ethyl groups revealed that high delta selectivity required an unmodified amino acid sequence. Shifts of Asp and hydrophobic residues decreased delta selectivity due to loss in delta affinity (5- to almost-equal-to 700-fold); mu affinity was unchanged or increased 14-fold. Suppression of charge or deamidation diminished delta selectivity through reduced delta and modified mu affinities. Data provide evidence that a negative charge does not a priori guarantee high selectivity and specific alignment of anionic and hydrophobic residues might facilitate optimum spatial configuration which complements the 8 receptor binding site.

  DOI：

  10.1016/0223-5234(92)90113-f