Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors.

[gm1 gangliosidosis]

N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1 -deoxygalactonojirimycin with a functionalised C ₆ alkyl chain followed by modification with different aromatic substituents provided lipophilic 1 -deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-glycosidases from E . coli and Agrobacterium sp . as well as green coffee bean α-galactosidase . In preliminary studies , these compounds also showed potential as chemical chaperones for GM 1 -gangliosidosis related β-galactosidase mutants .