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Peptide o ‐Aminoanilides as Crypto‐Thioesters for Protein Chemical Synthesis
Author(s) -
Wang JiaXing,
Fang GeMin,
He Yao,
Qu DaLiang,
Yu Min,
Hong ZhangYong,
Liu Lei
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408078
Subject(s) - native chemical ligation , peptide , moiety , chemistry , chemical ligation , chemical synthesis , combinatorial chemistry , peptide synthesis , convergent synthesis , biochemistry , stereochemistry , in vitro
Fully unprotected peptide o ‐aminoanilides can be efficiently activated by NaNO 2 in aqueous solution to furnish peptide thioesters for use in native chemical ligation. This finding enables the convergent synthesis of proteins from readily synthesizable peptide o ‐aminoanilides as a new type of crypto‐thioesters. The practicality of this approach is shown by the synthesis of histone H2B from five peptide segments. Purification or solubilization tags, which are sometimes needed to improve the efficiency of protein chemical synthesis, can be incorporated into the o ‐aminoanilide moiety, as demonstrated in the preparation of the cyclic protein lactocyclicin Q.