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. © 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
ALBERGHINA, LILIA;
2007
Abstract
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. © 2007 Elsevier B.V. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.