Facile Generation of Strained Peptidyl Thiolactones from Hydrazides and Its Application in Assembling MUC-1 VNTR OIigomers  

作　　者：Yuankun Dao Biao Wang Weidong Dong Jun Zhang Chao Zhong Zhili Zhang Suwei Dong 

机构地区：[1]State Key Laboratory of Natural and Biomimetic Drugs,and Department of Chemical Biology,School of Pharmaceutical Sciences,Peking University,Beijing 100191,China [2]Institute of Systems Biomedicine,School of Basic Medical Sciences,Peking University Health Science Center,Beijing 100191,China

出　　处：《Chinese Journal of Chemistry》2021年第9期2509-2516,共8页中国化学（英文版）

基　　金：The authors are grateful for financial support from the Beijing Natural Science Foundation(No.JQ18024);the National Natural Science Foundation of China(Nos.21822701,91953111,21672012);the Beijing Outstanding Young Scientist Program(No.BJJWZYJH01201910001001);State Key Laboratory of Natural and Biomimetic Drugs.

摘　　要：An efficient method for the activation of C-terminal 4-mecaptoproline-or penicillamine-containing peptide hydrazides in ligation re-actions is reported herein.The corresp on ding peptide hydrazides can be readily prepared using solid-phase peptide synthesis,and subsequently activated by acetylacet one(acac)without exoge nous thiol additives.Strained peptidyl thiolactones could be the possible reactive in termediates that drastically accelerate the reacti on rates at the sterically demandi ng proline and valine sites.This developed protocol allows for sequential peptide ligations in a one-pot manner,and expedites the assembly of mucin 1(MUC-1)variable number tandem repeat(VNTR)trimers in various glycosylated forms.

关 键 词：Strained molecules GLYCOPEPTIDES Synthetic methods Peptidyl thiolactones 

分 类 号：O62[理学—有机化学]