View references (35) Candida rugosa lipase crude preparations (CRL) catalyse the regioselective acylation of methyl 6-O-trytil β-d-glucopyranoside in organic solvents, using vinyl acetate as acyl donor. The ratio of the two products formed, namely methyl 2-O acetyl 6-O-trytil β-d-glucopyranoside and methyl 3-O acetyl 6-O-trytil β-d-glucopyranoside was found to be markedly affected by the nature of the reaction medium. In hydrophobic solvents values up to 80% of the monoacetylated product in position C-3 were obtained compared to less than 30% in solvents with low hydrophobicity. Computational studies were carried out to simulate the interactions between methyl 6-O-trytil β-d-glucopyranoside and both CRL and the solvents, in order to rationalize the experimental results

An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides

ALCARO S;ORTUSO F
2007-01-01

Abstract

View references (35) Candida rugosa lipase crude preparations (CRL) catalyse the regioselective acylation of methyl 6-O-trytil β-d-glucopyranoside in organic solvents, using vinyl acetate as acyl donor. The ratio of the two products formed, namely methyl 2-O acetyl 6-O-trytil β-d-glucopyranoside and methyl 3-O acetyl 6-O-trytil β-d-glucopyranoside was found to be markedly affected by the nature of the reaction medium. In hydrophobic solvents values up to 80% of the monoacetylated product in position C-3 were obtained compared to less than 30% in solvents with low hydrophobicity. Computational studies were carried out to simulate the interactions between methyl 6-O-trytil β-d-glucopyranoside and both CRL and the solvents, in order to rationalize the experimental results
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.12317/1469
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