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

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...

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Bibliographic Details
Published in:Bioprocess and biosystems engineering 2006-03, Vol.28 (4), p.227-233
Main Authors: FAZLENA, H, KAMARUDDIN, A. H, ZULKALI, M. M. D
Format: Article
Language:English
Subjects:
Biological and medical sciences
Biotechnology
Combinatorial Chemistry Techniques - methods
Computer Simulation
Fundamental and applied biological sciences. Psychology
Hydrolysis
Ibuprofen - chemical synthesis
Isomerism
Kinetics
Lipase - chemistry
Models, Chemical
Reproductive technologies
Sodium hydroxide
Sodium Hydroxide - chemistry
Temperature
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Summary: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.
ISSN:1615-7591
1615-7605
DOI:10.1007/s00449-005-0024-1