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Inverse Peptide Synthesis via Activated α‐Aminoesters
Author(s) -
Suppo JeanSimon,
Subra Gilles,
Bergès Matthieu,
Marcia de Figueiredo Renata,
Campagne JeanMarc
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402147
Subject(s) - tetrapeptide , epimer , peptide , chemistry , cysteine , combinatorial chemistry , peptide bond , residue (chemistry) , peptide synthesis , inverse , stereochemistry , organic chemistry , biochemistry , mathematics , geometry , enzyme
A mild, practical, and simple procedure for peptide‐bond formation is reported. Instead of activation of the carboxylic acid functionality, the reaction involves an unprecedented use of activated α‐aminoesters. The method provides a straightforward entry to dipeptides and was effective when a sensitive cysteine residue was used, as no epimerization was detected in this case. The applicability of this method to iterative peptide synthesis was illustrated by the synthesis of a model tetrapeptide in the challenging reverse N→C direction.