(S)-4-((S)-1-{Allyl-[(S)-1-((S)-1-{(S)-1-[(S)-3-tert-butoxycarbonyl-1-((S)-1-methoxycarbonyl-ethylcarbamoyl)-propylcarbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)-ethyl]-carbamoyl}-ethylcarbamoyl)-4-pent-4-enoylamino-butyric acid tert-butyl ester | 787632-51-3

• 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: (S)-4-((S)-1-{Allyl-[(S)-1-((S)-1-{(S)-1-[(S)-3-tert-butoxycarbonyl-1-((S)-1-methoxycarbonyl-ethylcarbamoyl)-propylcarbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)-ethyl]-carbamoyl}-ethylcarbamoyl)-4-pent-4-enoylamino-butyric acid tert-butyl ester
• CAS: 787632-51-3
• 化学式: C₄₂H₆₉N₇O₁₃
• 分子量: 880.049
• InChiKey: YOXNVHCYQSJGTB-FLMSMKGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  62.0
• 可旋转键数：
  25.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  273.81
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (S)-4-((S)-1-{Allyl-[(S)-1-((S)-1-{(S)-1-[(S)-3-tert-butoxycarbonyl-1-((S)-1-methoxycarbonyl-ethylcarbamoyl)-propylcarbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)-ethyl]-carbamoyl}-ethylcarbamoyl)-4-pent-4-enoylamino-butyric acid tert-butyl ester 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以55%的产率得到
  参考文献：
  名称：

  A Highly Stable Short α-Helix Constrained by a Main-Chain Hydrogen-Bond Surrogate

  摘要：

  Herein we describe a strategy for the preparation of artificial alpha-helices involving replacement of one of the main-chain hydrogen bonds with a covalent linkage. To mimic the C=O...H-N hydrogen bond as closely as possible, we envisioned a covalent bond of the type C=X-Y-N, where X and Y are two carbon atoms connected through an olefin metathesis reaction. Our results demonstrate that the replacement of a hydrogen bond between the i and i + 4 residues at the N-terminus of a short peptide with a carbon-carbon bond results in a highly stable constrained alpha-helix at physiological conditions as indicated by CD and NMR spectroscopies. The advantage of this strategy is that it allows access to short alpha-helices with strict preservation of molecular recognition surfaces required for biomolecular interactions.

  DOI：

  10.1021/ja0466659
• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-O-叔丁基-L-谷氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 以64.8%的产率得到(S)-4-((S)-1-{Allyl-[(S)-1-((S)-1-{(S)-1-[(S)-3-tert-butoxycarbonyl-1-((S)-1-methoxycarbonyl-ethylcarbamoyl)-propylcarbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)-ethyl]-carbamoyl}-ethylcarbamoyl)-4-pent-4-enoylamino-butyric acid tert-butyl ester
  参考文献：
  名称：

  A Highly Stable Short α-Helix Constrained by a Main-Chain Hydrogen-Bond Surrogate

  摘要：

  Herein we describe a strategy for the preparation of artificial alpha-helices involving replacement of one of the main-chain hydrogen bonds with a covalent linkage. To mimic the C=O...H-N hydrogen bond as closely as possible, we envisioned a covalent bond of the type C=X-Y-N, where X and Y are two carbon atoms connected through an olefin metathesis reaction. Our results demonstrate that the replacement of a hydrogen bond between the i and i + 4 residues at the N-terminus of a short peptide with a carbon-carbon bond results in a highly stable constrained alpha-helix at physiological conditions as indicated by CD and NMR spectroscopies. The advantage of this strategy is that it allows access to short alpha-helices with strict preservation of molecular recognition surfaces required for biomolecular interactions.

  DOI：

  10.1021/ja0466659

文献信息

• Methods for preparing internally constrained peptides and peptidomimetics
  申请人：New York University

  公开号：US09221871B2

  公开（公告）日：2015-12-29

  The present invention relates to a method for preparing a peptide having a stable, internally constrained alpha-helical, beta-sheet/beta-turn, 310-helical, or pi-helical region and a method of stabilizing an alpha-helical, beta-sheet/beta-turn, 310-helical, or pi-helical region within a peptide structure. The resulting peptides and methods of using them are also disclosed.

  本发明涉及一种制备具有稳定的内部约束α-螺旋、β-折叠/β-转角、310-螺旋或π-螺旋区域的肽的方法，以及稳定肽结构内α-螺旋、β-折叠/β-转角、310-螺旋或π-螺旋区域的方法。还公开了所得到的肽及其使用方法。