N-alkylated derivatives of 1,5-dideoxy-1,5-iminoxylitol as beta-xylosidase and beta-glucosidase inhibitors

A range of lipophilic derivatives of the D-xylosidase inhibitor 1,5-dideoxy-1,5-iminoxylitol was synthesized by N-alkylation of the parent compound with different alkyl halides. Inhibitory activities of the products obtained were measured with beta-glucosidase from Agrobacterium sp., a family I enzyme, as well as with beta-xylosidase from Thermoanaerobacterium saccharolyticum belonging to family 39 of the glycohydrolases. Whereas the former enzyme, which has low beta-xylosidase activity, was only moderately inhibited, with K-i values in the millimolar range, good inhibition was observed with the latter one. Inhibitors with terminally functionalized N-alkyl chains open up opportunities for novel applications as affinity ligands as well as for various types of tagging for diagnostic purposes.