L-phenylalanine<(1S)-1-methyloxycarbonyl-2-methylpropyl>ester | 161086-53-9

• 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: L-phenylalanine<(1S)-1-methyloxycarbonyl-2-methylpropyl>ester
• CAS: 161086-53-9
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: ROWKOJBZRGLRPS-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  草酰氯 、 L-phenylalanine<(1S)-1-methyloxycarbonyl-2-methylpropyl>ester 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以61%的产率得到(R)-2-((S)-2-{[(S)-1-((R)-1-Methoxycarbonyl-2-methyl-propoxycarbonyl)-2-phenyl-ethylaminooxalyl]-amino}-3-phenyl-propionyloxy)-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis of symmetrical pseudopeptides as potential inhibitors of the human immunodeficiency virus-1 protease

  摘要：

  It is demonstrated that HIV-1 protease is essential for the assembly and infectivity of the acquired immunodeficiency syndrome (AIDS) virus. This protease is an aspartyl protease with a 2-fold symmetry axis. Potential inhibitors were synthesized and consisted of a spacer linking 2 peptidic chains. They had to satisfy the following constraints: a C-2 symmetry axis, a backbone similar to the peptidic substrates, and side-chains filling the subsites S-n...S'(n). The compounds were synthesized via peptidic synthetic methods and evaluated in an enzymatic test with HIV-1 protease. Several compounds displayed an inhibitory activity at 10 mu M. They possessed the spacers CO, CO-CO, CO-CH2-CHOH-CO and the terminal chain Phe-O-iC(4)H(9). However, the structural-variation-based optimization of these different compounds failed and no potent inhibitors were prepared.

  DOI：

  10.1016/0223-5234(94)90025-6
• 作为产物：
  描述：

  (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyloxy)-3-methyl-butyric acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以81%的产率得到L-phenylalanine<(1S)-1-methyloxycarbonyl-2-methylpropyl>ester
  参考文献：
  名称：

  Synthesis of symmetrical pseudopeptides as potential inhibitors of the human immunodeficiency virus-1 protease

  摘要：

  It is demonstrated that HIV-1 protease is essential for the assembly and infectivity of the acquired immunodeficiency syndrome (AIDS) virus. This protease is an aspartyl protease with a 2-fold symmetry axis. Potential inhibitors were synthesized and consisted of a spacer linking 2 peptidic chains. They had to satisfy the following constraints: a C-2 symmetry axis, a backbone similar to the peptidic substrates, and side-chains filling the subsites S-n...S'(n). The compounds were synthesized via peptidic synthetic methods and evaluated in an enzymatic test with HIV-1 protease. Several compounds displayed an inhibitory activity at 10 mu M. They possessed the spacers CO, CO-CO, CO-CH2-CHOH-CO and the terminal chain Phe-O-iC(4)H(9). However, the structural-variation-based optimization of these different compounds failed and no potent inhibitors were prepared.

  DOI：

  10.1016/0223-5234(94)90025-6