Summary.
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 β-glucosidase from Agrobacterium sp., a family 1 enzyme, as well as with β-xylosidase from Thermoanaerobacterium saccharolyticum belonging to family 39 of the glycohydrolases. Whereas the former enzyme, which has low β-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.
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Received October 25, 2001. Accepted November 19, 2001
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Häusler, H., Rupitz, K., Stütz, A. et al. N-Alkylated Derivatives of 1,5-Dideoxy-1,5-iminoxylitol as β-Xylosidaseand β-Glucosidase Inhibitors. Monatshefte fuer Chemie 133, 555–560 (2002). https://doi.org/10.1007/s007060200028
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DOI: https://doi.org/10.1007/s007060200028