Powerful probes for glycosidases: Novel, fluorescently tagged glycosidase inhibitors

1-Amino-1,2,5-trideoxy-2,5-imino-D-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 beta -glucosidase exhibiting K-i values in the single figure nanosmolar range. The 1-N-dansyl substituted inhibitor was successfully exploited for binding studies with beta -glucosidase from Agrobacterium sp. employing fluorescence spectrometric methods. (C) 2001 Elsevier Science Ltd. All rights reserved.