Three-Component Synthesis of Neoglycopeptides Using a Cu(II)-Triggered Aminolysis of Peptide Hydrazide Resin and an Azide–Alkyne Cycloaddition Sequence

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-te...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (16), p.4336-4339
Main Authors: Ebran, Jean-Philippe, Dendane, Nabil, Melnyk, Oleg
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amines - chemistry
Azides - chemistry
Catalysis
Copper - chemistry
Glycopeptides - chemical synthesis
Molecular Structure
Oxidation-Reduction
Peptides - chemistry
Triazoles - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201659x