H-Tyr-Gly-Gly-Phe-Cys-Arg-Arg-D-Ala-Arg-Pro-Cys-NH2 | 127103-90-6

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: H-Tyr-Gly-Gly-Phe-Cys-Arg-Arg-D-Ala-Arg-Pro-Cys-NH2
• 英文别名: (3S,6R,9S,12S,15R,20R,23S)-15-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3,9,12-tris[3-(diaminomethylideneamino)propyl]-6-methyl-2,5,8,11,14,22-hexaoxo-17,18-dithia-1,4,7,10,13,21-hexazabicyclo[21.3.0]hexacosane-20-carboxamide
• CAS: 127103-90-6
• 化学式: C₅₄H₈₃N₂₁O₁₂S₂
• 分子量: 1282.52
• InChiKey: QXGFABTWRXRRJN-UUAWHVCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  89
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  615
• 氢给体数：
  18
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  5,Cys¹¹,D-Ala⁸>Dyn A_1-11 在 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 1.0h， 生成 H-Tyr-Gly-Gly-Phe-Cys-Arg-Arg-D-Ala-Arg-Pro-Cys-NH2
  参考文献：
  名称：

  Design and synthesis of highly potent and selective cyclic dynorphin A analogs

  摘要：

  We have designed and synthesized several cyclic disulfide-containing peptide analogues of dynorphin A (Dyn A) which are conformationally constrained in the putative "address" segment of the opioid ligand. Several of these Dyn A analogues exhibit unexpected selectivities for the kappa and mu opioid receptors(s) of the central vs peripheral nervous systems. Thus, incorporation of conformational constraint in the putative "address" segment of Dyn A analogues has resulted in the kappa/mu opioid receptor ligands [Cys5,Cys11]Dyn A1-11-NH2 (1) and [Cys5,Cys11,D-Ala8]Dyn A1-11-NH2 (2), which possess high kappa and mu opioid receptor affinities centrally (guinea pig brain, GPB), but only weak activity at peripheral kappa and mu opioid receptors (guinea pig ileum, GPI). On the other hand, [Cys8,Cys13]Dyn A1-13-NH2 and [D-Cys8,D-Cys13]Dyn A1-13-NH2 (5) display high kappa potencies and selectivities at the peripheral (GPI) but not at the central (GPB) kappa opioid receptor. The lack of correlation between the pharmacological profiles observed in smooth muscle and in the brain binding assays suggests the existence of different subtypes of the kappa and mu opioid receptors in the brain and peripheral nervous systems.

  DOI：

  10.1021/jm00169a007