On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2.

Subtilisin-catalyzed esterification of several enantiomeric benzyl and naph thyl glycopyranosides has been investigated. The D-sugar derivatives were a ll good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand , most of the L-glycopyranosides were transformed during longer reaction ti mes with a lower regioselectivity, the 2-OH being preferentially but not ex clusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.