An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides |
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Authors: | Palocci C Falconi M Alcaro S Tafi A Puglisi R Ortuso F Botta M Alberghina L Cernia E |
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Affiliation: | Dipartimento di Chimica, Università degli Studi di Roma "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy. cleofe.palocci@uniroma1.it |
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Abstract: | Candida rugosa lipase crude preparations (CRL) catalyse the regioselective acylation of methyl 6-O-trytil beta-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 beta-d-glucopyranoside and methyl 3-O acetyl 6-O-trytil beta-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 beta-d-glucopyranoside and both CRL and the solvents, in order to rationalize the experimental results. |
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