bis(Nα-amido-L-phenylalanine tert-butyl ester) fumarate

• 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 tert-butyl ester) fumarate
• 英文别名: tert-butyl (2S)-2-[[(E)-4-[[(2S)-1-[(2-methylpropan-2-yl)oxy]-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobut-2-enoyl]amino]-3-phenylpropanoate
• 化学式: C₃₀H₃₈N₂O₆
• 分子量: 522.642
• InChiKey: LBXDZNHHXDUJID-GKIAHDCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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 tert-butyl ester) fumarate 在 三氟乙酸 作用下， 反应 1.0h， 以90%的产率得到bis(Nα-amido-L-phenylalanine) fumarate
  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：

  L-苯丙氨酸叔丁酯盐酸盐 、 富马酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到bis(Nα-amido-L-phenylalanine tert-butyl ester) fumarate
  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

文献信息

• An Investigation of the Impact of Molecular Geometry upon Microcapsule Self-Assembly
  作者：Raymond J. Bergeron、Guo Wei Yao、Gregory W. Erdos、Sam Milstein、Fenglan Gao、William R. Weimar、Otto Phanstiel

  DOI：10.1021/ja00130a002

  日期：1995.6

  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.