Porcine pancreatic (PPL), Candida cylindracea (CCL) and Pseudomonas cepacia (LPS) lipases, suspended in organic solvents, were used to regioselectively acylate methyl 6-O-butyryl-alpha-D- and L-allopyranosides and methyl 6-O-butyryl-3-deoxy-alpha-D- and L-ribo-hexopyranosides. Both the D- and the L-3-deoxy sugars showed a complete regioselectivity, while the reactions of the allosides proved to be less regioselective. This indicates that the presence of the hydroxyl group at C-3 is an unfavourable factor for the action of the lipases.

Enzymic acylation of methyl D- and L-glycopyranosides: influence of the 3-hydroxyl group.

TOMA, LUCIO
1993-01-01

Abstract

Porcine pancreatic (PPL), Candida cylindracea (CCL) and Pseudomonas cepacia (LPS) lipases, suspended in organic solvents, were used to regioselectively acylate methyl 6-O-butyryl-alpha-D- and L-allopyranosides and methyl 6-O-butyryl-3-deoxy-alpha-D- and L-ribo-hexopyranosides. Both the D- and the L-3-deoxy sugars showed a complete regioselectivity, while the reactions of the allosides proved to be less regioselective. This indicates that the presence of the hydroxyl group at C-3 is an unfavourable factor for the action of the lipases.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/453823
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