[en] Given the potential of peptide selenoesters for protein total synthesis and the paucity of methods for the synthesis of these sensitive peptide derivatives, we sought to explore the usefulness of the bis(2-selenylethyl)amido (SeEA) group, i.e. the selenium analog of the bis(2-sulfanylethyl)amido (SEA) group, for accelerating peptide bond formation. A chemoselective exchange process operating in water was devised for converting SEA peptides into the SeEA ones. Kinetic studies show that SeEA ligation, which relies on an initial N,Se-acyl shift process, proceeds significantly faster than SEA ligation. This property enabled the design of a kinetically controlled three peptide segment assembly process based on the sequential use of SeEA and SEA ligation reactions. The method was validated by the total synthesis of hepatocyte growth factor K1 (85 AA) and biotinylated NK1 (180 AA) domains
Disciplines :
Chemistry
Author, co-author :
Raibaut, Laurent; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Cargoët, Marine; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Ollivier, Nathalie; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Chang, Yun Min; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Drobecq, Hervé; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Boll, Emmanuelle; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Desmet, Rémi; Université de Lille, Institut Pasteur de Lille > UMR CNRS 8161
Monbaliu, Jean-Christophe ✱; Université de Liège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis
Melnyk, Oleg ✱; Université de Lille, Institut Pasteur de Lille UMR > CNRS 8161
✱ These authors have contributed equally to this work.
Language :
English
Title :
Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates
Publication date :
2016
Journal title :
Chemical Science
ISSN :
2041-6520
eISSN :
2041-6539
Publisher :
Royal Society of Chemistry, Cambridge, United Kingdom
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