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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Published inOrganic & biomolecular chemistry Vol. 14; no. 47; pp. 11230 - 11237
Main Authors Jobin, Steve, Mejean, Alexia, Galindo, Sindy-Marcela, Liang, Xinxia, Vezina-Dawod, Simon, Biron, Eric
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 29.11.2016
Subjects
Amino Acid Sequence
Chemistry
Chemistry, Organic
Microwaves
Peptide Fragments - chemical synthesis
Peptide Fragments - chemistry
Physical Sciences
Science & Technology
Solid-Phase Synthesis Techniques - methods
RESIN
AMINO-ACID
STAUDINGER LIGATION
SERINE
CHEMISTRY
PROTEINS
MACROCYCLIZATION
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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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02342h