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© Fabrice Chrétien with Ultrapole, colorized by Jean-Marc Panaud
Cellule souche (en jaune) de muscle squelettique partiellement recouverte par la membrane basale, migrant sur une fibre musculaire (en bleu).
Publication : Bioorganic & medicinal chemistry

‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Bioorganic & medicinal chemistry - 27 Oct 2014

Lamandé-Langle S, Collet C, Hensienne R, Vala C, Chrétien F, Chapleur Y, Mohamadi A, Lacolley P, Regnault V

Link to Pubmed [PMID] – 25457125

Bioorg. Med. Chem. 2014 Dec;22(23):6672-83

‘Click’ glycosylation of cysteine-containing peptides were carried out in good yield by Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC). For that peptides were functionalized though direct propargylation of the cysteine residue allowing their use in CuAAC with suitable free or protected azido sugars of gluco, manno and galacto configuration. Among these free and protected glycopeptides a series of ‘glycoRGD’ peptides were obtained and submitted to in vitro platelet aggregation tests, showing that the pseudoglycosylation of the adhesion sequence lowers the IC50 value and thus could improve the in vivo pharmacokinetic properties.

http://www.ncbi.nlm.nih.gov/pubmed/25457125