(2R)-2-[[[(1S)-1-amino-3-phenylpropyl]-hydroxyphosphoryl]methyl]-3-phenylpropanoic acid | 920529-32-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R)-2-[[[(1S)-1-amino-3-phenylpropyl]-hydroxyphosphoryl]methyl]-3-phenylpropanoic acid
• CAS: 920529-32-4
• 化学式: C₁₉H₂₄NO₄P
• 分子量: 361.378
• InChiKey: QELOIXSGJMIHBZ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三甲基溴硅烷 、 盐酸 作用下， 反应 72.0h， 生成 (2R)-2-[[[(1S)-1-amino-3-phenylpropyl]-hydroxyphosphoryl]methyl]-3-phenylpropanoic acid
  参考文献：
  名称：

  Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase

  摘要：

  Individual stereoisomers of the phosphinic pseudodipeptide hPhe psi P(O)(OH) CH2]Phe were obtained by stereoselective liquid chromatographic separation as N- and C-terminally protected derivative on quinidine carbamate modified silica stationary phase. The stereoisomeric purity, exceeding 95% for each fraction, was determined before and after deprotection using two independent methods. The absolute configuration was rationally assigned by application of enantiomerically pure phosphinic acid substrates in the synthetic procedure and correlation with biological activity of the products. Substantial differences in inhibition of leucine aminopeptidase by the individual isomers revealed novel insights into potency of the recently developed and remarkably effective compound. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.107

文献信息

• Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase
  作者：Artur Mucha、Michael Lämmerhofer、Wolfgang Lindner、Małgorzata Pawełczak、Paweł Kafarski

  DOI：10.1016/j.bmcl.2008.01.107

  日期：2008.3

  Individual stereoisomers of the phosphinic pseudodipeptide hPhe psi P(O)(OH) CH2]Phe were obtained by stereoselective liquid chromatographic separation as N- and C-terminally protected derivative on quinidine carbamate modified silica stationary phase. The stereoisomeric purity, exceeding 95% for each fraction, was determined before and after deprotection using two independent methods. The absolute configuration was rationally assigned by application of enantiomerically pure phosphinic acid substrates in the synthetic procedure and correlation with biological activity of the products. Substantial differences in inhibition of leucine aminopeptidase by the individual isomers revealed novel insights into potency of the recently developed and remarkably effective compound. (c) 2008 Elsevier Ltd. All rights reserved.