title: Lipase-catalyzed regioselective monoacetylation of unsymmetrical 1,5-primary diols.
abstract: Lipase B from Candida antarctica (CALB) has been selected as the most suitable enzyme to catalyze the regioselective monoacetylation of 1,5-diol isoprostane intermediate, using vinyl acetate as an acyl transfer reagent in THF. We next applied this reaction on linear 2-substituted, 2,2'-disubstituted-1,5-pentanediols, and cyclic 2,3-disubstituted-1,5-pentanediols. To rationalize the regioselectivity observed, molecular docking simulations were performed.
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR 5247 CNRS, Université Montpellier I, Faculté de Pharmacie, 15 avenue Charles Flahault, BP 14491, 34093 Montpellier, Cedex 05, France.
authors.forename: Camille
authors.initials: C
authors.lastname: Oger
authors.forename: Zsuzsanna
authors.initials: Z
authors.lastname: Marton
authors.forename: Yasmin
authors.initials: Y
authors.lastname: Brinkmann
authors.forename: Valérie
authors.initials: V
authors.lastname: Bultel-Poncé
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
authors.forename: Marianne
authors.initials: M
authors.lastname: Graber
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Galano
mesh_terms: D000107:Acetylation; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D003198:Computer Simulation; D006900:Hydroxylation; D028421:Isoprostanes / Q000737:chemistry; D008049:Lipase / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D028421:Isoprostanes; D008049:Lipase