N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolyl-glycine benzyl ester | 901139-29-5

• 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: N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
• 英文别名: N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolylglycine benzyl ester；tert-butyl (2S,4S)-4-methyl-2-[(2-oxo-2-phenylmethoxyethyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 901139-29-5
• 化学式: C₂₀H₂₈N₂O₅
• 分子量: 376.453
• InChiKey: RAXHIYIPSZXYEK-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.5h， 生成 N-9-fuorenylmethoxycarbonyl-(2S)-prolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
  参考文献：
  名称：

  Reciprocity of Steric and Stereoelectronic Effects in the Collagen Triple Helix

  摘要：

  In previous work, we demonstrated that 4-fluoroproline residues can contribute greatly to the conformational stability of the collagen triple helix, and that this stability arises from stereoelectronic effects that fix the pucker of the pyrrolidine ring and thereby preorganize the backbone properly for triple-helix formation. Here, we take a reciprocal approach, demonstrating that the steric effect of a 4-methyl group confers stability similar to that from a 4-fluoro group in the opposite configuration. Such fundamental interplay between steric and stereoelectronic effects is heretofore unknown in proteins-natural or synthetic-and provides a new means to modulate conformational stability.

  DOI：

  10.1021/ja061793d
• 作为产物：
  描述：

  (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-methylenepyrrolidine 在 镍 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 乙腈 为溶剂， 反应 45.0h， 生成 N-tert-butyloxycarbonyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
  参考文献：
  名称：

  Reciprocity of Steric and Stereoelectronic Effects in the Collagen Triple Helix

  摘要：

  In previous work, we demonstrated that 4-fluoroproline residues can contribute greatly to the conformational stability of the collagen triple helix, and that this stability arises from stereoelectronic effects that fix the pucker of the pyrrolidine ring and thereby preorganize the backbone properly for triple-helix formation. Here, we take a reciprocal approach, demonstrating that the steric effect of a 4-methyl group confers stability similar to that from a 4-fluoro group in the opposite configuration. Such fundamental interplay between steric and stereoelectronic effects is heretofore unknown in proteins-natural or synthetic-and provides a new means to modulate conformational stability.

  DOI：

  10.1021/ja061793d

文献信息

• Collagen mimics
  申请人：Raines T. Ronald

  公开号：US20070275897A1

  公开（公告）日：2007-11-29

  Novel collagen mimics are disclosed with a tripeptide unit having the formula (Xaa-Yaa-Gly) n , where one of the positions Xaa or Yaa is a bulky, non-electron withdrawing proline derivative. By substituting a proline derivative at either the Xaa or Yaa position in the native collagen helix, the stability of the helix is increased due solely to steric effects relative to prior known collagen-related triple helices. Methods are also disclosed for making the novel collagen mimics.

  揭示了一种具有三肽单元的新型胶原模拟物，其化学式为（Xaa-Yaa-Gly）n，其中Xaa或Yaa位置中的一个是体积庞大的非电子吸引脯氨酸衍生物。通过在原生胶原螺旋中的Xaa或Yaa位置之一替换脯氨酸衍生物，仅通过立体效应相对于先前已知的胶原相关三肽螺旋，可以增加螺旋的稳定性。还揭示了制备新型胶原模拟物的方法。
• COLLAGEN MIMICS
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20180030115A1

  公开（公告）日：2018-02-01

  Novel collagen mimics are disclosed with a tripeptide unit having the formula (Xaa-Yaa-Gly) n , where one of the positions Xaa or Yaa is a bulky, non-electron withdrawing proline derivative. By substituting a proline derivative at either the Xaa or Yaa position in the native collagen helix, the stability of the helix is increased due solely to steric effects relative to prior known collagen-related triple helices. Methods are also disclosed for making the novel collagen mimics.
• US9758569B2
  申请人：——

  公开号：US9758569B2

  公开（公告）日：2017-09-12
• Reciprocity of Steric and Stereoelectronic Effects in the Collagen Triple Helix
  作者：Matthew D. Shoulders、Jonathan A. Hodges、Ronald T. Raines

  DOI：10.1021/ja061793d

  日期：2006.6.1

  In previous work, we demonstrated that 4-fluoroproline residues can contribute greatly to the conformational stability of the collagen triple helix, and that this stability arises from stereoelectronic effects that fix the pucker of the pyrrolidine ring and thereby preorganize the backbone properly for triple-helix formation. Here, we take a reciprocal approach, demonstrating that the steric effect of a 4-methyl group confers stability similar to that from a 4-fluoro group in the opposite configuration. Such fundamental interplay between steric and stereoelectronic effects is heretofore unknown in proteins-natural or synthetic-and provides a new means to modulate conformational stability.