Preparation of Peptide Selenoesters from Their Corresponding Acyl Hydrazides

• 作者: Yunxue Li Jiazhi Liu Qingqing Zhou Jie Zhao Ping Wang
• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2021,（7）
• 所属期刊栏目: Concise Reports
• 页码范围: 1861-1866
• 页数: 6页
• 语种: 英文
• DOI: 10.1002/cjoc.202100086

摘要

Main observation and conclusion Selenoesters are useful substitutes for traditional thioesters in protein ligation chemistry due to their high reactivity in the trans-thio/selenoesterification reaction.However,existing synthetic routes to access peptide selenoester require a selenoesterifica-tion reaction between a selenide and a protected peptide with a free carboxylate at the C-terminus.Herein,we introduce an efficient method to convert peptide acyl hydrazide,a convenient thioester surrogate,into the desired selenoester for peptide ligation.Our methodology can be applied to fully de-protected peptides with various C-terminal amino acid residues in high yield without racemi-zation.We believe that this method provides a useful alternative to access peptide C-terminal selenoesters for protein ligation.