6-Amino-6-deoxy-5,6-di-N-(N′-octyliminomethylidene)nojirimycin: Synthesis, Biological Evaluation, and Crystal Structure in Complex with Acid β-Glucosidase

Abstract

6-Amino-6-deoxy-5,6-di-N-(N′-octyliminomethylidene)nojirimycin, a reducing analogue of N-nonyl-1-deoxynojirimycin, proved to be a potent and very selective inhibitor of β-glucosidases, including human acid β-glucosidase. Structural studies of the enzyme–inhibitor complex showed a binding mode in which the anomeric hydroxy group is accommodated in the “wrong” α configuration.