An approach to address Candida rugosa lipase regioselectivity in the acylation reactions of trytilated glucosides.
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.
Palocci
C
C
Dipartimento di Chimica, Università degli Studi di Roma "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy. cleofe.palocci@uniroma1.it
Falconi
M
M
Alcaro
S
S
Tafi
A
A
Puglisi
R
R
Ortuso
F
F
Botta
M
M
Alberghina
L
L
Cernia
E
E
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
D005960:Glucosides; D012997:Solvents; D014753:Vinyl Compounds; D008049:Lipase; C011566:vinyl acetate