Effect of co-solvent addition on the reaction kinetics of the lipase-catalyzed resolution of ibuprofen ester
MetadataShow full item record
BACKGROUND: The addition of co-solvent is not limited to enhancing the catalytic rate, it could also assist in situ racemization in the dynamic kinetic resolution of racemic compounds by increasing the reactivity of the base catalyst employed. In the current work, reaction media with the presence of DMSO were investigated in Candida rugosa lipase (EC 184.108.40.206)-catalyzed hydrolysis of ibuprofen ester that focuses on the thermodynamic effect, reaction stability and implication for the kinetic parameters. RESULTS: The introduction of 2% DMSO increased the reaction rate, conversion, and enantioselectivity of the Candida rugosa lipase-mediated resolution. However, the performance of the particular enzymatic reaction was reduced when a higher DMSO concentration was added. At lower reaction temperatures, the medium with 2% DMSO exhibited an increase in enantioselectivity, which was attributed to a higher activation energy difference between the fast- and slow-reacting enantiomers compared with the water-isooctane medium. Additionally, the presence of DMSO had a significant effect on the kinetic parameters, shown by a lower value of Michaelis constant compared with that of a normal reaction without DMSO, which resulted in a fast reaction rate. Finally, inhibition due to the uncompetitive substrate inhibitor was reduced, while the non-competitive product inhibitor consequently increased. CONCLUSION: This work has demonstrated that only 2% of DMSO can be tolerated by the free Candida rugosa lipase in the resolution of ibuprofen ester. However, it is still able to give significant positive effects on the hydrolysis rate, kinetic parameters and enantioselectivity as well as reaction stability.
Showing items related by title, author, creator and subject.
Jia, Huanfei (2002)This thesis investigates an application of immobilized lipase for pre-treating wastewater containing fats and oils, which is difficult to treat practically. The kinetics of soluble lipase was studied for establishing ...
Lau, Sie Yon; Gonawan, Fadzil; Kamaruddin, Azlina; Uzir, Mohamad (2013)Ibuprofen (isobutyl-propanoic-phenolic acid) is a chiral drug which essentially well-known for its analgesic, antipyretic and anti-inflammatory effects. In the present work, an enzymatic membrane reactor (EMR) has been ...
Catalytic partial oxidation of propylene to acrolein: the catalyst structure, reaction mechanisms and kineticsFansuri, Hamzah (2005)Bismuth molybdates have long been known as active catalysts for selective oxidation of olefins. There are several phases of bismuth molybdates but only three of them are known to be active for partial oxidation of propylene ...