6-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]hexanoic acid | 1028254-31-0

• 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: 6-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]hexanoic acid
• CAS: 1028254-31-0
• 化学式: C₄₅H₅₃N₅O₈
• 分子量: 791.945
• InChiKey: KWUCRDXFQGLWCH-MXVPUGLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  58
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  209
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]hexanoic acid 在 哌啶 、 吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 H-Phe-c[-N^ε-Lys-Tyr-Ahx-]
  参考文献：
  名称：

  Design and Synthesis of Motilin Antagonists Derived from the [1−4] Fragment of Porcine Motilin

  摘要：

  A series of cyclic peptides having the general structure H-Phe-c[-N-epsilon-Lys-X-NH-(CH2)(n)-CO-] were designed on the basis of structure-activity relationship studies of motilin. All were motilin antagonists. The cyclic peptides, in which X is a 3-tert-butyl-substituted tyrosine residue (H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-betaAla-] (3), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Gly-] (6), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Abu-] (7), and H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Ahx-] (8)) showed potent motilin receptor antagonistic activity in the rabbit smooth muscle (pA(2) > 7). The 3-tert-butyl Tyr was found to be the moiety responsible for enhanced binding to the motilin receptor, while the size of the ring had little importance.

  DOI：

  10.1021/jm010332u
• 作为产物：
  描述：

  N-芴甲氧羰基-N'-叔丁氧羰基-L-赖氨酸五氟苯酯 、 芴甲氧羰基-O-叔丁基-L-酪氨酸五氟苯酯 、 N-芴甲氧羰基-L-苯丙氨酸五氟苯酯 、 芴甲氧羰酰基-6-氨基己酸 生成 6-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]hexanoic acid
  参考文献：
  名称：

  Design and Synthesis of Motilin Antagonists Derived from the [1−4] Fragment of Porcine Motilin

  摘要：

  A series of cyclic peptides having the general structure H-Phe-c[-N-epsilon-Lys-X-NH-(CH2)(n)-CO-] were designed on the basis of structure-activity relationship studies of motilin. All were motilin antagonists. The cyclic peptides, in which X is a 3-tert-butyl-substituted tyrosine residue (H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-betaAla-] (3), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Gly-] (6), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Abu-] (7), and H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Ahx-] (8)) showed potent motilin receptor antagonistic activity in the rabbit smooth muscle (pA(2) > 7). The 3-tert-butyl Tyr was found to be the moiety responsible for enhanced binding to the motilin receptor, while the size of the ring had little importance.

  DOI：

  10.1021/jm010332u

文献信息

• Design and Synthesis of Motilin Antagonists Derived from the [1−4] Fragment of Porcine Motilin
  作者：Masayuki Haramura、Akira Okamachi、Kouichi Tsuzuki、Kenji Yogo、Makoto Ikuta、Toshiro Kozono、Hisanori Takanashi、Eigoro Murayama

  DOI：10.1021/jm010332u

  日期：2002.1.1

  A series of cyclic peptides having the general structure H-Phe-c[-N-epsilon-Lys-X-NH-(CH2)(n)-CO-] were designed on the basis of structure-activity relationship studies of motilin. All were motilin antagonists. The cyclic peptides, in which X is a 3-tert-butyl-substituted tyrosine residue (H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-betaAla-] (3), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Gly-] (6), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Abu-] (7), and H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Ahx-] (8)) showed potent motilin receptor antagonistic activity in the rabbit smooth muscle (pA(2) > 7). The 3-tert-butyl Tyr was found to be the moiety responsible for enhanced binding to the motilin receptor, while the size of the ring had little importance.