title: Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles.
abstract: Glycosyl 1,2,3-triazoles with alpha-D-gluco, beta-D-gluco, alpha-D-galacto, beta-D-galacto and beta-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 beta-N-acetylhexosaminidase. Beta-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors.
authors.affiliation: Centre of Biocatalysis and Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídenská 1083, CZ 14220, Prague, Czech Republic.
authors.forename: Kristýna
authors.initials: K
authors.lastname: Slámová
authors.forename: Petr
authors.initials: P
authors.lastname: Marhol
authors.forename: Karel
authors.initials: K
authors.lastname: Bezouska
authors.forename: Lise
authors.initials: L
authors.lastname: Lindkvist
authors.forename: Signe G
authors.initials: SG
authors.lastname: Hansen
authors.forename: Vladimír
authors.initials: V
authors.lastname: Kren
authors.forename: Henrik H
authors.initials: HH
authors.lastname: Jensen
mesh_terms: D000818:Animals; D006801:Humans; D006868:Hydrolysis; D051381:Rats; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D014230:Triazoles