Exploring a Multivalent Approach to α‐<scp>L</scp>‐Fucosidase Inhibition

Abstract

Abstract To probe the utility of a multivalent approach for fucosidase inhibition, a series of di‐ and tri‐valent imino sugars based on L ‐fuco ‐configured 1,4‐imino‐ and 1,4‐bis(imino)‐cyclitol epitopes has been synthesized and analyzed for fucosidase inhibition with the best trivalent species yielding a modest improvement in binding constant. Structural analysis of a representative pair of mono‐ and tri‐valent imino sugars has been performed on a bacterial fucosidase, Bt Fuc2970. The 3D structures show binding of the imino‐cyclitol in the 3 E conformation, consistent with the known pathway for fucosidase action.