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

摘要

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 abtained were measured with #beta#-glucosidase from Agrobacterium sp.,a family 1 enzyme,as well as with #beta#-zylosidase from Thermoanaerobacterium saccharolyticum belonging to family 39 of the glycohydrolases.Whereas the former enzyme,which has low #beta#-zylosidase activity,was only moderately inhibited,with K_i values in the millimolar range,good inhibition was observed with the latter one.Inhibited,with terminally functionalized N-alkyl chains open up opportunities for novel applications as affinity lignds as well as for various types of tagging for diagnostic purposes.