Premium
Formation and Rearrangement of Homoserine Depsipeptides and Depsiproteins in the α‐Ketoacid–Hydroxylamine Ligation with 5‐Oxaproline
Author(s) -
Wucherpfennig Thomas G.,
Rohrbacher Florian,
Pattabiraman Vijaya R.,
Bode Jeffrey W.
Publication year - 2014
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.201406097
Subject(s) - depsipeptide , hydroxylamine , chemistry , amide , ligation , stereochemistry , native chemical ligation , combinatorial chemistry , chemical synthesis , biochemistry , biology , microbiology and biotechnology , in vitro
The primary products of the chemical ligation of α‐ketoacids and 5‐oxaproline peptides are esters, rather than the previously reported amides. The depsipeptide product rapidly rearranges to the amide in basic buffers. The formation of esters sheds light on possible mechanisms for the type II KAHA ligations and opens an avenue for the chemical synthesis of depsiproteins.