Literature

Abstract

'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.

DOI： 10.1016/j.bmc.2014.09.056

‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC

Bioorganic & Medicinal Chemistry 2014.0

Click reaction synthesis of carbohydrate derivatives from ristocetin aglycon with antibacterial and antiviral activity

Bioorganic & Medicinal Chemistry Letters 2010.0

Glycosidase inhibition by 1-glycosyl-4-phenyl triazoles

Bioorganic & Medicinal Chemistry Letters 2005.0

‘Click chemistry’ synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase

Bioorganic & Medicinal Chemistry 2010.0

Synthesis of 3′-azido-3′-deoxythymidine (AZT)—Cinchona alkaloid conjugates via click chemistry: Toward novel fluorescent markers and cytostatic agents

Bioorganic & Medicinal Chemistry Letters 2011.0

Synthesis of 1,4-triazole linked zanamivir dimers as highly potent inhibitors of influenza A and B