Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production

Abstract

A lipase catalysed enantioselective hydrolysis process under in situ racemization of the remaining (R)-ibuprofen ester substrate with sodium hydroxide as the catalyst was developed for the production of S-ibuprofen from (R,S)-ibuprofen ester in isooctane. Detailed investigations on parameters study indicated that 0.5 M NaOH, addition of 20% (v/v) co-solvent (dimethyl sulphoxide), operating temperature of 45 degrees C, and 40 mmol/L substrate gave 86% conversion and 99.4% optical purity of S-ibuprofen in dynamic kinetic resolution. Meanwhile, in common enzymatic kinetic resolution process, only 42% conversion of the racemate and 93% enantiomeric excess of the product was obtained which are of lower values as compared to dynamic kinetic resolution. The S-ibuprofen produced during each process was evaluated and approximately 50% increment in concentration of S-acid product was produced when dynamic kinetic resolution was applied into the process.

Biochemical characterization of immobilized tannase from Aspergillus awamori

“…Thus, further studies were performed on immobilized tannase on amberlite. Amberlite is considered to be better immobilization matrix for various other enzymes such as urease (Anita et al, 1997), lipase (Fazlena et al, 2006), and R-galactosidase (Onal and Telefoncu 2005), and fructosyltransferase (Platková et al, 2006).…”

Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid‐base catalysis

“…The undesired enantiomer (R)-ibuprofen was racemized in basic ethylene glycolwater (It has been reported that (R)-ibuprofen ethoxyethyl ester can be racemized in basic DMSO-water. 19 ) and then re-resolved. The (S)-ester was separated and hydrolyzed to produce (S)-ibuprofen.…”

“…Recently, Candida rugosa lipase, 15,16 Rhizomucor miehei lipase, 17 and Aspergillus niger lipase 8 have been used for the chiral resolution of (R,S)-ibuprofen through mainly direct enantioselective esterification in organic media; Lipase from C. rugosa (Type VII), 18,19 Pseudomonas cepacia lipase, 20 and Pseudomonas fluorescens lipase 21 have been used to catalyze enantioselective hydrolysis of its chemically synthesized racemic ester.…”

Chemoenzymatic Kinetic resolution of (R)-malathion in aqueous media

“…The value of enantioselectivity ( E ) was calculated from the enantiomeric excess of the substrate ( ee ) and the conversion degree ( c ) according to the equations 1 and 2 described by Chen et al [23]. …”