Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles |
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Authors: | Kristýna Slámová Petr Marhol Karel Bezouška Lise Lindkvist Signe G. Hansen Vladimír Křen Henrik H. Jensen |
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Affiliation: | 1. Centre of Biocatalysis and Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 14220, Prague, Czech Republic;2. Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark;3. Department of Biochemistry, Faculty of Science, Charles University Prague, Hlavova 8, CZ-12840 Praha 2, Czech Republic |
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Abstract: | Glycosyl 1,2,3-triazoles with α-d-gluco, β-d-gluco, α-d-galacto, β-d-galacto and β-2-acetamido-2-deoxygluco (GlcNAc) stereochemistry were prepared by reaction of the corresponding azides with vinyl acetate under microwave irradiation. The deprotected glucosyl and galactosyl triazoles did not display inhibitory activity against the tested glycosidases at 1 mM. Of the four fungal glycosidases evaluated, GlcNAc-triazole was found to be hydrolyzed by Talaromyces flavus CCF 2686 β-N-acetylhexosaminidase. β-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors. |
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