2-[2-({1-[2-(2-{[1-(2,2-dimethylpropionyl)pyrrolidine-2-carbonyl]amino}benzoylamino)benzoyl]pyrrolidine-2-carbonyl}amino)benzoylamino]benzoic acid methyl ester | 1448441-07-3

• 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: 2-[2-({1-[2-(2-{[1-(2,2-dimethylpropionyl)pyrrolidine-2-carbonyl]amino}benzoylamino)benzoyl]pyrrolidine-2-carbonyl}amino)benzoylamino]benzoic acid methyl ester
• 英文别名: methyl 2-[[2-[[(2R)-1-[2-[[2-[[(2S)-1-(2,2-dimethylpropanoyl)pyrrolidine-2-carbonyl]amino]benzoyl]amino]benzoyl]pyrrolidine-2-carbonyl]amino]benzoyl]amino]benzoate
• CAS: 1448441-07-3
• 化学式: C₄₄H₄₆N₆O₈
• 分子量: 786.885
• InChiKey: XKRPAFZCQONUNX-XDSPJLLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  58
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[2-({1-[2-(2-{[1-(2,2-dimethylpropionyl)pyrrolidine-2-carbonyl]amino}benzoylamino)benzoyl]pyrrolidine-2-carbonyl}amino)benzoylamino]benzoic acid methyl ester 、 甲胺 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到2-[2-({1-[2-(2-{[1-(2,2-dimethylpropionyl)pyrrolidine-2-carbonyl]amino}benzoylamino)benzoyl]pyrrolidine-2-carbonyl}amino)benzoylamino]benzoic acid methyl amide
  参考文献：
  名称：

  A Synthetic Zipper Peptide Motif Orchestrated via Co-operative Interplay of Hydrogen Bonding, Aromatic Stacking, and Backbone Chirality

  摘要：

  Here, we report on a new class of synthetic zipper peptide which assumes its three-dimensional zipper-like structure via a co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality. Structural studies carried out in both solid- and solution-state confirmed the zipper-like structural architecture assumed by the synthetic peptide which makes use of unusually remote inter-residual hydrogen-bonding and aromatic stacking interactions to attain its shape. The effect of chirality modulation and the extent of noncovalent forces in the structure stabilization have also been comprehensively explored via single-crystal X-ray diffraction and solution-state NMR studies. The results highlight the utility of noncovalent forces in engineering complex synthetic molecules with intriguing structural architectures.

  DOI：

  10.1021/ja405455g
• 作为产物：
  描述：

  2-硝基苯甲酰氯 在 甲醇 、 palladium(II) hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-[2-({1-[2-(2-{[1-(2,2-dimethylpropionyl)pyrrolidine-2-carbonyl]amino}benzoylamino)benzoyl]pyrrolidine-2-carbonyl}amino)benzoylamino]benzoic acid methyl ester
  参考文献：
  名称：

  A Synthetic Zipper Peptide Motif Orchestrated via Co-operative Interplay of Hydrogen Bonding, Aromatic Stacking, and Backbone Chirality

  摘要：

  Here, we report on a new class of synthetic zipper peptide which assumes its three-dimensional zipper-like structure via a co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality. Structural studies carried out in both solid- and solution-state confirmed the zipper-like structural architecture assumed by the synthetic peptide which makes use of unusually remote inter-residual hydrogen-bonding and aromatic stacking interactions to attain its shape. The effect of chirality modulation and the extent of noncovalent forces in the structure stabilization have also been comprehensively explored via single-crystal X-ray diffraction and solution-state NMR studies. The results highlight the utility of noncovalent forces in engineering complex synthetic molecules with intriguing structural architectures.

  DOI：

  10.1021/ja405455g