Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
Vijay V. Gottemukkala
Kalyan K. Saripella
Anil K. Kadari
Steven H. Neau*
Financial support: The NIH supported this research through grant GM061565-01 A2.
Keywords: enantioselective, esterification, ibuprofen, lipase, solvent-effect, water activity.
The purpose of this research was to study the effect of the methyl branching of a high log P alkane solvent and the water activity in the organic medium on the initial rate and the enantioselectivity of ibuprofen esterification catalyzed by Candida rugosa lipase. Resolution of ibuprofen is important because S-(+)-ibuprofen has the desired pharmacological activity, whereas the R-(-)-enantiomer causes much of the side effects. The Candida rugosa lipase-catalyzed reaction in isooctane at 40ºC and 0.73 water activity gave the best results, both in terms of the initial reaction rate and the enantioselectivity of the reaction. An increase in water activity allowed a higher reaction rate and enantiomeric excess in each of the four solvents. An increase in methyl branching did not necessarily increase the initial reaction rate, but it allowed a higher enantioselectivity, evidenced by an increase in the substrate enantiomeric excess.