title: Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation.
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.
authors.affiliation: CNRS UMR 8161, Univ. Lille Nord de France, Institut Pasteur de Lille, 59021 Lille, France.
authors.forename: Reda
authors.initials: R
authors.lastname: Mhidia
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Boll
authors.forename: Fabien
authors.initials: F
authors.lastname: Fécourt
authors.forename: Mikhail
authors.initials: M
authors.lastname: Ermolenko
authors.forename: Nathalie
authors.initials: N
authors.lastname: Ollivier
authors.forename: Kaname
authors.initials: K
authors.lastname: Sasaki
authors.forename: David
authors.initials: D
authors.lastname: Crich
authors.forename: Bernard
authors.initials: B
authors.lastname: Delpech
authors.forename: Oleg
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D001216:Asparagine / Q000737:chemistry*; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007094:Imides; D010455:Peptides; D001216:Asparagine