bis(Nα-amido-L-phenylalanine benzyl ester) oxalate | 161086-59-5

• 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: bis(Nα-amido-L-phenylalanine benzyl ester) oxalate
• 英文别名: benzyl (2S)-2-[[2-[[(1S)-1-benzyl-2-benzyloxy-2-oxo-ethyl]amino]-2-oxo-acetyl]amino]-3-phenyl-propanoate；benzyl (2S)-2-[[2-oxo-2-[[(2S)-1-oxo-3-phenyl-1-phenylmethoxypropan-2-yl]amino]acetyl]amino]-3-phenylpropanoate
• CAS: 161086-59-5
• 化学式: C₃₄H₃₂N₂O₆
• 分子量: 564.638
• InChiKey: NZQTZSGVVZKCHF-KYJUHHDHSA-N

物化性质

• 密度：
  1.238±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(Nα-amido-L-phenylalanine benzyl ester) oxalate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以100%的产率得到bis(Nα-amido-L-phenylalanine) oxalate
  参考文献：
  名称：

  An Investigation of the Impact of Molecular Geometry upon Microcapsule Self-Assembly

  摘要：

  Bis-amide dicarboxylic acids derived from the condensation of malonic acid, 1,1-dimethylmalonic acid, 1,1-cyclopropane dicarboxylic acid, or maleic acid with L-phenylalanine, (L-Phe), are shown to supramolecularly self-assemble in aqueous solution. When basic solutions of these diacids are taken to pH 2.4, microcapsules are formed. Scanning and transmission electron micrographs confirm that microcapsules and not solid microspheres are generated. The ability of these assemblies to encapsulate other materials present during their formation in water was demonstrated with a tannic acid marker. Structure-activity studies clearly demonstrate the importance of a cis geometry between L-Phe fragments for self-assembly. Molecular modeling revealed that the cis geometry of 1a, 5a, and 14 imparts a helical structure to these systems. The subsequent self-association via hydrogen bonds of these hydrophobic helical diacids is postulated as the mechanism for their self-assembly, Nonmicrocapsule forming scaffolds (predicated on oxalic, fumaric, and succinic acid backbones) favored ''cuplike'' or pocket geometries which were not conducive to intermolecular aggregation.

  DOI：

  10.1021/ja00130a002
• 作为产物：
  描述：

  草酰氯 、 3-苯基-L-丙氨酸苄酯 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以50%的产率得到bis(Nα-amido-L-phenylalanine benzyl ester) oxalate
  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