title: An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides.
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.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Roma "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy. cleofe.palocci@uniroma1.it
authors.forename: C
authors.initials: C
authors.lastname: Palocci
authors.forename: M
authors.initials: M
authors.lastname: Falconi
authors.forename: S
authors.initials: S
authors.lastname: Alcaro
authors.forename: A
authors.initials: A
authors.lastname: Tafi
authors.forename: R
authors.initials: R
authors.lastname: Puglisi
authors.forename: F
authors.initials: F
authors.lastname: Ortuso
authors.forename: M
authors.initials: M
authors.lastname: Botta
authors.forename: L
authors.initials: L
authors.lastname: Alberghina
authors.forename: E
authors.initials: E
authors.lastname: Cernia
mesh_terms: D000215:Acylation; D002175:Candida / Q000201:enzymology*; D005960:Glucosides / Q000378:metabolism*; D057927:Hydrophobic and Hydrophilic Interactions; D008049:Lipase / Q000378:metabolism*; D008958:Models, Molecular; D012997:Solvents / Q000737:chemistry; D014753:Vinyl Compounds / Q000378:metabolism
chemical_list: D005960:Glucosides; D012997:Solvents; D014753:Vinyl Compounds; D008049:Lipase; C011566:vinyl acetate