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. (c) 2007 Elsevier B.V. All rights reserved.

Palocci, C., Falconi, M., Alcaro, S., Tafi, A., Puglisi, R., Ortuso, F., et al. (2007). An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides. JOURNAL OF BIOTECHNOLOGY, 128(4), 908-918 [10.1016/j.jbiotec.2006.08.019].

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

Tafi, Andrea;Botta, Maurizio;
2007-01-01

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. (c) 2007 Elsevier B.V. All rights reserved.
2007
Palocci, C., Falconi, M., Alcaro, S., Tafi, A., Puglisi, R., Ortuso, F., et al. (2007). An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides. JOURNAL OF BIOTECHNOLOGY, 128(4), 908-918 [10.1016/j.jbiotec.2006.08.019].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/4206
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