Synthesis of α-L-fucopyranosyl disaccharides with thioglycosidic linkages and characterization of α-L-fucosidases from bovine kidney and epididymis by their inhibitory activities

Abstract Sulfur-linked disaccharide analogs of three α- L -fucopyranosyl 2-acetamido-2-deoxy-β- D -glucopyranosides and one α- L -fucopyranosyl β- D -galactopyranoside were synthesized by substitution reactions of sulfonates and ring-opening reactions of aziridine as well as oxirane derivatives using 1-thio-α- L -fucopyranose as nucleophile. Fucosidases from bovine kidney and epididymis were inhibited by all of these disaccharide analogs and their Ki values range from 0.65 to 4.9 mM.