(Z)-(2R)-5-(N-(Benzyloxycarbonyl)amino)-4-fluoro-2-(2-methylpropyl)-3-pentenoic acid | 163810-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-(2R)-5-(N-(Benzyloxycarbonyl)amino)-4-fluoro-2-(2-methylpropyl)-3-pentenoic acid
• 英文别名: (Z,2R)-4-fluoro-2-(2-methylpropyl)-5-(phenylmethoxycarbonylamino)pent-3-enoic acid
• CAS: 163810-37-5
• 化学式: C₁₇H₂₂FNO₄
• 分子量: 323.364
• InChiKey: KZTNUHNIAZNYCB-WJQTUHTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(2R)-5-(N-(Benzyloxycarbonyl)amino)-4-fluoro-2-(2-methylpropyl)-3-pentenoic acid 在 ammonium hydroxide 、 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 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到(Z)-(2R)-5-(N-(Benzyloxycarbonyl)amino)-4-fluoro-2-(2-methylpropyl)-3-pentenamide
  参考文献：
  名称：

  Fluoroalkenes as Peptide Isosteres: Ground State Analog Inhibitors of Thermolysin

  摘要：

  Tripeptide analogs of the form Cbz-Gly Psi[(Z)-CF=CH]LeuXaa (1, Xaa = Gly, Ala, Leu, Phe, and NH2) were synthesized to assess the ability of the fluoroalkene moiety to mimic a peptide linkage. These compounds are modest inhibitors of the zinc endopeptidase thermolysin (0.19 mM < K-i < 1.8 mM); the K-i values correlate strongly with the K-m, values, but not K-m/k(cat), for hydrolysis of the corresponding peptides. The correlation indicates that these inhibitors bind as ground state analogs and represent the first direct assessment of the fluoroalkene unit as a peptide surrogate.

  DOI：

  10.1021/jo00115a028
• 作为产物：
  描述：

  N-(Benzyloxycarbonyl)-N-((Z)-(4R)-2-fluoro-4-(hydroxymethyl)-6-methyl-2-heptenyl)amine 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以91%的产率得到(Z)-(2R)-5-(N-(Benzyloxycarbonyl)amino)-4-fluoro-2-(2-methylpropyl)-3-pentenoic acid
  参考文献：
  名称：

  Fluoroalkenes as Peptide Isosteres: Ground State Analog Inhibitors of Thermolysin

  摘要：

  Tripeptide analogs of the form Cbz-Gly Psi[(Z)-CF=CH]LeuXaa (1, Xaa = Gly, Ala, Leu, Phe, and NH2) were synthesized to assess the ability of the fluoroalkene moiety to mimic a peptide linkage. These compounds are modest inhibitors of the zinc endopeptidase thermolysin (0.19 mM < K-i < 1.8 mM); the K-i values correlate strongly with the K-m, values, but not K-m/k(cat), for hydrolysis of the corresponding peptides. The correlation indicates that these inhibitors bind as ground state analogs and represent the first direct assessment of the fluoroalkene unit as a peptide surrogate.

  DOI：

  10.1021/jo00115a028

文献信息

• Fluoroalkenes as Peptide Isosteres: Ground State Analog Inhibitors of Thermolysin
  作者：Paul A. Bartlett、Atsushi Otake

  DOI：10.1021/jo00115a028

  日期：1995.5

  Tripeptide analogs of the form Cbz-Gly Psi[(Z)-CF=CH]LeuXaa (1, Xaa = Gly, Ala, Leu, Phe, and NH2) were synthesized to assess the ability of the fluoroalkene moiety to mimic a peptide linkage. These compounds are modest inhibitors of the zinc endopeptidase thermolysin (0.19 mM < K-i < 1.8 mM); the K-i values correlate strongly with the K-m, values, but not K-m/k(cat), for hydrolysis of the corresponding peptides. The correlation indicates that these inhibitors bind as ground state analogs and represent the first direct assessment of the fluoroalkene unit as a peptide surrogate.