Subtilisin-catalyzed esterification of several enatiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all 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 times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated.
On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2 / B. Danieli, F. Peri, G. Roda, G. Carrea, S. Riva. - In: TETRAHEDRON. - ISSN 0040-4020. - 55:7(1999), pp. 2045-2060. [10.1016/S0040-4020(98)01217-4]
On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2
B. Danieli;G. Roda;
1999
Abstract
Subtilisin-catalyzed esterification of several enatiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all 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 times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated.
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