Powerful probes for glycosidases: novel, fluorescently tagged glycosidase inhibitors[]

1-Amino-1,2,5-trideoxy-2,5-imino- -mannitol was fluorescently tagged by reaction with dansyl chloride at N-1 or by attachment of a dansyl amide bearing spacer to this centre. Compounds obtained are highly potent inhibitors of β-glucosidase exhibiting Ki values in the single figure nanomolar range. The 1-N-dansyl substituted inhibitor was successfully exploited for binding studies with β-glucosidase from Agrobacterium sp. employing fluorescence spectrometric methods.