Toward solid-phase peptide fragment ligation by a traceless-Ugi multicomponent reaction approach

A new methodology to couple peptide fragments on solid support using a traceless isocyanide-based multicomponent reaction is described. The approach uses a microwave-assisted on-resin Ugi four-component reaction to attach a carboxyl free peptide to a supported peptide bearing a free N-terminal amine...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-11, Vol.14 (47), p.11230-11237
Main Authors: Jobin, Steve, Méjean, Alexia, Galindo, Sindy-Marcela, Liang, Xinxia, Vézina-Dawod, Simon, Biron, Eric
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Microwaves
Peptide Fragments - chemical synthesis
Peptide Fragments - chemistry
Solid-Phase Synthesis Techniques - methods
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Summary:A new methodology to couple peptide fragments on solid support using a traceless isocyanide-based multicomponent reaction is described. The approach uses a microwave-assisted on-resin Ugi four-component reaction to attach a carboxyl free peptide to a supported peptide bearing a free N-terminal amine via the formation of an N-protected amide bond at the ligation site. Afterward, the generated backbone amide protecting group can be efficiently removed by microwave-assisted acidolysis with trifluoroacetic acid to afford a fully deprotected peptide. This straightforward Ugi reaction/deprotection approach was applied to condense various fragment lengths and provided a variety of oligopeptides.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02342h