title: Three-component synthesis of neoglycopeptides using a Cu(II)-triggered aminolysis of peptide hydrazide resin and an azide-alkyne cycloaddition sequence.
abstract: Copper(II)-induced oxidative aminolysis of hydrazides generates Cu(I), the catalyst of the azide-alkyne cycloaddition. This feature was exploited to design a novel solid phase detaching three-component reaction permitting the conversion of supported peptide hydrazides into 1,2,3-triazole linked C-terminal neoglycopeptides.
authors.affiliation: CNRS UMR 8161, Univ Lille Nord de France, Institut Pasteur de Lille, IFR 142 Molecular and Cellular Medicine, 1 rue du Pr Calmette 59021 Lille Cedex, France.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Ebran
authors.forename: Nabil
authors.initials: N
authors.lastname: Dendane
authors.forename: Oleg
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D006020:Glycopeptides; D010455:Peptides; D014230:Triazoles; D003300:Copper