Boc-Trp-Lys(Tac)-D-Asp-N-MePhe-NH2

• 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-Trp-Lys(Tac)-D-Asp-N-MePhe-NH2
• 英文别名: Boc-Trp-hCit(Ph(2-Me))(Ph(2-Me))-D-Asp-N(Me)Phe-NH2；(3R)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-methylamino]-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-6-[(2-methylphenyl)carbamoylamino]hexanoyl]amino]-4-oxobutanoic acid
• 化学式: C₄₄H₅₆N₈O₉
• 分子量: 840.977
• InChiKey: KNHCBYMGWWTGSO-KFIZHRIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  254
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-(S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoic (isobutyl carbonic) anhydride 在 10percent Pd/C 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 Boc-Trp-Lys(Tac)-D-Asp-N-MePhe-NH2
  参考文献：
  名称：

  CCK Peptides with Combined Features of Hexa- and Tetrapeptide CCK-A Agonists

  摘要：

  Selective CCK-A agonist activity has been reported to induce satiety in a variety of animals, including man, and thereby suggests a therapeutic role for CCK in the management of obesity. To date, three general classes of CCK-A agonists have been reported, the full-length, sulfated hepta- and hexapeptides, a series of tetrapeptides, and most recently a series of benzodiazepines. The SAR of the hexa- and tetrapeptide classes suggests that the Hpa(SO3H) and Tac groups may not interact at the CCK-A receptor in the same location. However, the C-terminal dipeptide part of the hexapeptides and tetrapeptides appear to interact at the CCK-A receptor in a similar manner. Compound 7 (Hpa-Nle-Gly-Trp-Lys(Tac)-Asp-MePhe-NH2) derived from combining the features of the hexapeptides and the tetrapeptides has subnanomolar affinity and 3500-fold selectivity for CCK-A receptors. Compound 7 administered intraperitoneally produces potent, long-lasting reduction in food intake in rats and a corresponding weight loss when administered over nine consecutive days.

  DOI：

  10.1021/jm990252e

文献信息

• CCK Peptides with Combined Features of Hexa- and Tetrapeptide CCK-A Agonists
  作者：M. Edward Pierson、Jeanne M. Comstock、Roy D. Simmons、Ronald Julien、Frederick Kaiser、James D. Rosamond

  DOI：10.1021/jm990252e

  日期：2000.6.1

  Selective CCK-A agonist activity has been reported to induce satiety in a variety of animals, including man, and thereby suggests a therapeutic role for CCK in the management of obesity. To date, three general classes of CCK-A agonists have been reported, the full-length, sulfated hepta- and hexapeptides, a series of tetrapeptides, and most recently a series of benzodiazepines. The SAR of the hexa- and tetrapeptide classes suggests that the Hpa(SO3H) and Tac groups may not interact at the CCK-A receptor in the same location. However, the C-terminal dipeptide part of the hexapeptides and tetrapeptides appear to interact at the CCK-A receptor in a similar manner. Compound 7 (Hpa-Nle-Gly-Trp-Lys(Tac)-Asp-MePhe-NH2) derived from combining the features of the hexapeptides and the tetrapeptides has subnanomolar affinity and 3500-fold selectivity for CCK-A receptors. Compound 7 administered intraperitoneally produces potent, long-lasting reduction in food intake in rats and a corresponding weight loss when administered over nine consecutive days.