5-Thio-L-fucose

Hashimoto, H, Fujimori, T, Yuasa, H, Synthesis of 5-thio-L-fucose and its inhibitory effect on fucosidase, J. Carbohydr. Chem., 9, 683-694, 1990. 

Izumi, M, Tsuruta, O, Harayama, S, Hashimoto, H, S3mthesis of 5-thio-L-fucose-containing disaccharides, as sequence-specific inhibitors, and 2 -fucosyllactose, as a substrate of a-L-fucosidases, J. Org. Chem., 62, 992-998, 1997. 

Thio-D-maimose 329,5-tliio-D-galactose 330,5-thio-L-altrose 331, and 5-thio-L-fucose 332" were synthesized using as the key steps the conversion of a terminal oxirane into thiirane with thiourea, and the opening of the thiirane... 

Hashimoto et al. reported that 5-thio-L-fucose (332) is a potent inhibitor of a-L-fucosidase from bovine epididymis (AT = 42 whereas replacement of... 

The synthesis and some reactions of 4,5-epithio-2,3-di-0-methanesulphonyl-L-xylose dimethyl acetal (41) are summarised in Scheme 9, and Scheme 10 shows the preparation of 3-0-acetyl-5,6-epithio-l,2-0-isopropylidene-a-L-galactofuranose (43) from the D-altrose compound (42) - itself available in ten steps from D-glucose - and its conversion to 5-thio-L-fucose (44), an inhibitor of a-fucosidases. ... 

The following are not substrates D>allose, D-galactose 4-deoxy-glucose, 4>deoxy-fluoroglucose, 5-thio-D glucose, L-rhamnose, L-fucose, L-sorbose. 

---