(R)-tert-butyl 2-((2-((2-(methoxycarbonyl)phenyl)carbamoyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate | 1225014-70-9

• 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: (R)-tert-butyl 2-((2-((2-(methoxycarbonyl)phenyl)carbamoyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate
• 英文别名: 2-[2-(2-methoxycarbonylphenylcarbamoyl)phenylcarbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 1225014-70-9
• 化学式: C₂₅H₂₉N₃O₆
• 分子量: 467.522
• InChiKey: CCBVBRAZHDLBOY-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 2-((2-((2-(methoxycarbonyl)phenyl)carbamoyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate 在 甲醇 、 palladium(II) hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (R)-1-(2-(2-aminobenzamido)benzoyl)-N-(2-((2-(methylcarbamoyl)phenyl)carbamoyl)phenyl)pyrrolidine-2-carboxamide
  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：

  N-(tert-butoxycarbonyl)-D-proline 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-tert-butyl 2-((2-((2-(methoxycarbonyl)phenyl)carbamoyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate
  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

文献信息

• Switching the H-bonding network of a foldamer by modulating the backbone chirality and constitutional ratio of amino acids
  作者：Veera V. E. Ramesh、Kuruppanthara N. Vijayadas、Snehal Dhokale、Rajesh G. Gonnade、Pattuparambil R. Rajamohanan、Gangadhar J. Sanjayan

  DOI：10.1039/c3ob41369a

  日期：——

  This communication describes the folding propensity of a heterofoldamer motif featuring proline (Pro) and anthranilic acid (Ant) residues in a 1 : 2 : 1 (α : β : α) constitutional ratio. Structural investigations unequivocally suggest that the hydrogen-bonding network of this foldamer motif can be switched between 9-membered and 6-membered by modulating the backbone chirality and constitutional ratio of the amino acid residues.

  这篇通讯描述了一种异折叠器图案的折叠倾向，该图案以脯氨酸（Pro）和蚁酸（Ant）残基为特征，两者的结构比为 1 : 2 ：1 : 2 : 1 (α : β : α) 的结构比例。结构研究明确表明，通过调节氨基酸残基的骨架手性和构型比例，该折叠器图案的氢键网络可以在 9 元和 6 元之间切换。