Enzymatic resolution of 3-butene-1,2-diol in organic solvents and optimization of reaction conditions

Lipases from different sources were tested in the kinetic resolution of 2-h ydroxy-3-butenyl butanoate [(R,S)-2] carried out by transesterification of the secondary alcohol. The influence of organic solvent. acyl donor and tem perature on the enantioselectivity and activity of lipases was also investi gated. Our study showed that both R-(+)-2 and S-(-)-2 could be obtained in high enantiomeric purity (ee greater than or equal to 99%) and satisfactory yield (29% and 27%, respectively). Among the enzymes tested, lipase from C andida antarctica B (CALB) showed the highest preference for the (R)-enanti omer (E = 26 at -13 degrees C), whereas lipase from Pseudomonas fluorescens (lipase AK) acylated the (S)-enantiomer preferentially (E = 18 at -9 degre es C).