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Facile Generation of Strained Peptidyl Thiolactones from Hydrazides and Its Application in Assembling MUC ‐1 VNTR Oligomers †
Author(s) -
Dao Yuankun,
Wang Biao,
Dong Weidong,
Zhang Jun,
Zhong Chao,
Zhang Zhili,
Dong Suwei
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202100326
Subject(s) - chemistry , peptide , steric effects , stereochemistry , combinatorial chemistry , peptide synthesis , biochemistry
Main observation and conclusion An efficient method for the activation of C ‐terminal 4‐mecaptoproline‐ or penicillamine‐containing peptide hydrazides in ligation reactions is reported herein. The corresponding peptide hydrazides can be readily prepared using solid‐phase peptide synthesis, and subsequently activated by acetylacetone (acac) without exogenous thiol additives. Strained peptidyl thiolactones could be the possible reactive intermediates that drastically accelerate the reaction rates at the sterically demanding 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.