Boc-Dmt-D-Arg(NO2)-Phe-Lys(Z)-OMe | 865173-22-4

• 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: Boc-Dmt-D-Arg(NO2)-Phe-Lys(Z)-OMe
• 英文别名: Boc-Tyr(2,6-diMe)-D-Arg(NO2)-Phe-Lys(Cbz)-OMe；methyl (2S)-2-[[(2S)-2-[[(2R)-5-[[amino(nitramido)methylidene]amino]-2-[[(2S)-3-(4-hydroxy-2,6-dimethylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentanoyl]amino]-3-phenylpropanoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 865173-22-4
• 化学式: C₄₆H₆₃N₉O₁₂
• 分子量: 934.059
• InChiKey: KCAIVRVVYPJZDJ-SPWOZAQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  67
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  307
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Boc-Dmt-D-Arg(NO2)-Phe-Lys(Z)-OMe 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 TFA*H-Dmt-D-Arg(NO2)-Phe-Lys(Z)-OH
  参考文献：
  名称：

  From the Potent and Selective μ Opioid Receptor Agonist H-Dmt-d-Arg-Phe-Lys-NH₂ to the Potent δ Antagonist H-Dmt-Tic-Phe-Lys(Z)-OH

  摘要：

  H-Dmt-D-Arg-Phe-Lys-NH2 ([Dmt(1)]DALDA) binds with high affinity and selectivity to the mu opioid receptor and is a potent and long-acting analgesic. Substitution of D-Arg in position 2 with Tic and masking of the lysine amine side chain by Z protection and of the C-terminal carboxylic function instead of the amide function transform a potent and selective mu agonist into a potent and selective delta antagonist H-Dmt-Tic-Phe-Lys(Z)-OH. Such a delta antagonist could be used as a pharmacological tool.

  DOI：

  10.1021/jm0504959
• 作为产物：
  描述：

  TFA*H-D-Arg(NO2)-Phe-Lys(Z)-OMe 、 N-Boc-2,6-二甲基-L-酪氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以90%的产率得到Boc-Dmt-D-Arg(NO2)-Phe-Lys(Z)-OMe
  参考文献：
  名称：

  From the Potent and Selective μ Opioid Receptor Agonist H-Dmt-d-Arg-Phe-Lys-NH₂ to the Potent δ Antagonist H-Dmt-Tic-Phe-Lys(Z)-OH

  摘要：

  H-Dmt-D-Arg-Phe-Lys-NH2 ([Dmt(1)]DALDA) binds with high affinity and selectivity to the mu opioid receptor and is a potent and long-acting analgesic. Substitution of D-Arg in position 2 with Tic and masking of the lysine amine side chain by Z protection and of the C-terminal carboxylic function instead of the amide function transform a potent and selective mu agonist into a potent and selective delta antagonist H-Dmt-Tic-Phe-Lys(Z)-OH. Such a delta antagonist could be used as a pharmacological tool.

  DOI：

  10.1021/jm0504959