Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation

Reda Mhidia; Emmanuelle Boll; Fabien Fécourt; Mikhail Ermolenko; Nathalie Ollivier; Kaname Sasaki; David Crich; Bernard Delpech; Oleg Melnyk

doi:10.1016/j.bmc.2013.02.053

Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation

Bioorg Med Chem. 2013 Jun 15;21(12):3479-85. doi: 10.1016/j.bmc.2013.02.053. Epub 2013 Mar 24.

Authors

Reda Mhidia¹, Emmanuelle Boll, Fabien Fécourt, Mikhail Ermolenko, Nathalie Ollivier, Kaname Sasaki, David Crich, Bernard Delpech, Oleg Melnyk

Affiliation

¹ CNRS UMR 8161, Univ. Lille Nord de France, Institut Pasteur de Lille, 59021 Lille, France.

PMID: 23602526
DOI: 10.1016/j.bmc.2013.02.053

Abstract

Imide capture of a C-terminal peptidylazide with a side-chain thioacid derivative of an N-terminally protected aspartyl peptide leads to the formation of an imide bond bringing the two peptide ends into close proximity. Unmasking of the N(α) protecting group and intramolecular acyl migration results in the formation of a native peptide bond to asparagine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Asparagine / chemistry*
Imides / chemical synthesis
Imides / chemistry*
Molecular Conformation
Peptides / chemical synthesis*
Peptides / chemistry

Substances

Imides
Peptides
Asparagine