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

TitleN-alkylated derivatives of 1,5-dideoxy-1,5-iminoxylitol as beta-xylosidase and beta-glucosidase inhibitors
Publication TypeJournal Article
Year of Publication2002
AuthorsHausler, H, RUPITZ, K, Stutz, AE, Withers, SG
JournalMONATSHEFTE FUR CHEMIE
Volume133
Pagination555-560
Date PublishedAPR
ISSN0026-9247
Abstract

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.

DOI10.1007/s007060200028