(S)-1-Trityl-aziridine-2-carboxylic acid pentafluorophenyl ester | 157878-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-1-Trityl-aziridine-2-carboxylic acid pentafluorophenyl ester
• CAS: 157878-50-7
• 化学式: C₂₈H₁₈F₅NO₂
• 分子量: 495.448
• InChiKey: SKOZKUJFKGPYOR-FGKHMDTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  亮氨酰-精氨酸 、 (S)-1-Trityl-aziridine-2-carboxylic acid pentafluorophenyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以83%的产率得到Trt-Azy-Leu-Arg-OH
  参考文献：
  名称：

  On the synthesis of (2S)-aziridine-2-carboxylic acid containing peptides

  摘要：

  Optimized conditions are described for the synthesis of 1-trityl-2-aziridine-carboxylic acid 3 (Trt-Azy-OH) and benzyl (2S)-aziridine-2-carboxylate 6 (H-Azy-OBzl) as useful derivatives for the synthesis of N- and C-terminal aziridine-containing peptides. Thereby, the use of the pentafluorophenyl ester of Trt-Azy-OH was found to be the method of choice in acylating steps, whereas acylation of H-Azy-OBzl several classical methods of peptide synthesis can be successfully used. The fully protected aziridine-2-carboxylic acid peptides are accessible in satisfactory yields as analytically defined products, but partial or total deprotection of these compounds again by standard procedures of peptide synthesis is surprisingly difficult in terms of satisfactory yields, whereby sequence-dependent unstability both in the reaction and purification steps as well as on storage was found to strongly limit the accessibility of these aziridine-containing peptides as promising active-site inactivators of cysteine-proteinases.

  DOI：

  10.1016/s0040-4020(01)80847-4
• 作为产物：
  描述：

  benzyl (S)-1-tritylaziridine-2-carboxylate 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 (S)-1-Trityl-aziridine-2-carboxylic acid pentafluorophenyl ester
  参考文献：
  名称：

  On the synthesis of (2S)-aziridine-2-carboxylic acid containing peptides

  摘要：

  Optimized conditions are described for the synthesis of 1-trityl-2-aziridine-carboxylic acid 3 (Trt-Azy-OH) and benzyl (2S)-aziridine-2-carboxylate 6 (H-Azy-OBzl) as useful derivatives for the synthesis of N- and C-terminal aziridine-containing peptides. Thereby, the use of the pentafluorophenyl ester of Trt-Azy-OH was found to be the method of choice in acylating steps, whereas acylation of H-Azy-OBzl several classical methods of peptide synthesis can be successfully used. The fully protected aziridine-2-carboxylic acid peptides are accessible in satisfactory yields as analytically defined products, but partial or total deprotection of these compounds again by standard procedures of peptide synthesis is surprisingly difficult in terms of satisfactory yields, whereby sequence-dependent unstability both in the reaction and purification steps as well as on storage was found to strongly limit the accessibility of these aziridine-containing peptides as promising active-site inactivators of cysteine-proteinases.

  DOI：

  10.1016/s0040-4020(01)80847-4