Synthesis of 1→6,1→4 and 1→3 linked 1-thio-α-L-fucopyranosyl 2-acetamido-2-deoxy-β-D-glucopyranosides and 1→2 linked β-D-galactopyranoside, and their linkage-specific inhibitory activities toward α-L-fucosidases

Abstract Sulfur-linked disaccharides analogs of three α- L -fucopyranosyl 2-acetamido-2-deoxy-β- D -gluco pyranosides 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 derivative 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.