157865-35-5Relevant 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
Izumi,Tsuruta,Harayama,Hashimoto
, p. 992 - 998 (1997)
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.
