Lipase-catalyzed regioselective monoacetylation of unsymmetrical 1,5-primary diols

Abstract

"Chemical Equation Presented" 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 TIIF. We next applied this reaction on linear 2-substituted, 2,2′-disubstituted-l,5pentanediols, and, cyclic 2,3-disubstituted-l,5-pentanediols. To rationalize the regioselectivity observed, molecular docking simulations were performed. © 2010 American Chemical Society.