186967-60-2

Upstream product

• 114853-38-2 methyl 1-thio-β-L-fucopyranoside 
• 84635-54-1 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 72200-51-2 2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal 
• 77667-97-1 O-(6-O-acetyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal 
• 157865-35-5 methyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 

Relevant academic research and scientific papers

Synthesis of 5-thio-L-fucose-containing disaccharides, as sequence-specific inhibitors, and 2'-fucosyllactose, as a substrate of α-L-fucosidases

Four 5-thio-L-fucose-containing disaccharides having α(1→6), α(1→3), α(1→4)GlcNAc, and α(1→2)Gal linkages (compounds 1-4, respectively) were synthesized as potential α-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3·OEt2 as a catalyst gave mainly α-linked disaccharides. Only α(1→2)-linked disaccharide 4 showed inhibitory activity (K(i) = 0.21 mM) against Bacillus α-L-fucosidase which hydrolyzes the Fucα(1→2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K(i) = 30-91 μM) against bovine epididymis α-L-fucosidase.