Porcine pancreatic (PPL), Candida cylindracea (CCL) and Pseudomonas cepacia (LPS) lipases, suspended in organic solvents, were used to regioselectively acylate methyl 6-O-butyryl-α-D- and L-allopyranosides and methyl 6-O-butyryl-3-deoxy-α-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 / D. Colombo, F.C.V. Ronchetti, A. Scala, I.M. Taino,L. Toma. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 1:5(1993), pp. 375-380. [10.1016/S0968-0896(00)82144-6]
Enzymic acylation of methyl D- and L-glycopyranosides: Influence of the 3-hydroxyl group
D. ColomboPrimo
;F.C.V. RonchettiSecondo
;A. Scala;
1993
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-α-D- and L-allopyranosides and methyl 6-O-butyryl-3-deoxy-α-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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