The Synthesis of 3-O-(β-D-Glucopyranosyl)- and 3-O-(β-Laminaribiosyl)-isofagomines, Potent Inhibitors of a 1,3-β-D-Glucan endo-Hydrolase

Abstract

The glycosylation of 4,6-O-benzylidene-N-benzyloxycarbonylisofagomine with a D-glucosyl and a laminari-biosyl trichloroacetimidate has given, after removal of protecting groups, 3-O-(β-D-glucopyranosyl)- and 3-O-(β-laminaribiosyl)-isofagomines. Also included are similar glycosylations of a related tetrahydrooxazine. 3-O-(β-D-Glucopyranosyl)- and 3-O-(β-laminaribiosyl)-isofagomines acted as potent inhibitors of a barley 1,3-β-D-glucan endo-hydrolase, with ID₅₀ values of 7.8 and 3.1 μM, respectively.