3-pyridin-4-ylpropyl (2S)-2-[methoxy-[(1R)-2-phenyl-1-[[(2S)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoyl]amino]ethyl]phosphoryl]oxy-3-phenylpropanoate | 175918-15-7

• 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: 3-pyridin-4-ylpropyl (2S)-2-[methoxy-[(1R)-2-phenyl-1-[[(2S)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoyl]amino]ethyl]phosphoryl]oxy-3-phenylpropanoate
• CAS: 175918-15-7
• 化学式: C₃₉H₄₅N₄O₉P
• 分子量: 744.781
• InChiKey: KHVOGJPORIDRPA-OKTSQJRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  53
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-pyridin-4-ylpropyl (2S)-2-[methoxy-[(1R)-2-phenyl-1-[[(2S)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoyl]amino]ethyl]phosphoryl]oxy-3-phenylpropanoate 在 Dowex-Li⁺ 、 叔丁胺 作用下， 反应 14.0h， 以18%的产率得到3-(4-pyridyl)propyl (2S)-2-[({(1R)-1-[N-(N-{[(phenylmethoxy)carbonyl]glycyl}-L-alanyl)amino]-2-phenylethyl}hydroxyphosphinyl)oxy]-3-phenylpropanoate, lithium salt
  参考文献：
  名称：

  Transition State Analogy of Phosphonic Acid Peptide Inhibitors of Pepsin

  摘要：

  A series of 11 phosphonate peptide analogs, RO(2)C-Xaa-Yaa-Phe-(PO2--O)-Phe O-(3-(4-pyridyl)propyl ester), were synthesized and evaluated as inhibitors of the aspartic peptidase pepsin. For the inhibitors with Gly or Ala at the P-2 position, the K-i values correlate with the K-m/k(cat) values of the corresponding substrates, demonstrating that these analogs mimic the transition state in the way the P-2-P-4 residues bind. Deviations from the correlation for the other inhibitor/substrate pairs imply a different binding orientation as a result of N-substitution at P-2 (Pro), contamination with the more potent diastereomer (D-Ala), or a change in rate-limiting step for turnover (lie).

  DOI：

  10.1021/jo952074c
• 作为产物：
  描述：

  4-吡啶丙醇 在 palladium dihydroxide 4-二甲氨基吡啶 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 36.08h， 生成 3-pyridin-4-ylpropyl (2S)-2-[methoxy-[(1R)-2-phenyl-1-[[(2S)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoyl]amino]ethyl]phosphoryl]oxy-3-phenylpropanoate
  参考文献：
  名称：

  Transition State Analogy of Phosphonic Acid Peptide Inhibitors of Pepsin

  摘要：

  A series of 11 phosphonate peptide analogs, RO(2)C-Xaa-Yaa-Phe-(PO2--O)-Phe O-(3-(4-pyridyl)propyl ester), were synthesized and evaluated as inhibitors of the aspartic peptidase pepsin. For the inhibitors with Gly or Ala at the P-2 position, the K-i values correlate with the K-m/k(cat) values of the corresponding substrates, demonstrating that these analogs mimic the transition state in the way the P-2-P-4 residues bind. Deviations from the correlation for the other inhibitor/substrate pairs imply a different binding orientation as a result of N-substitution at P-2 (Pro), contamination with the more potent diastereomer (D-Ala), or a change in rate-limiting step for turnover (lie).

  DOI：

  10.1021/jo952074c