Process Biotechnology
 

Microbial Biotechnology

Electronic Journal of Biotechnology ISSN: 0717-3458 Vol. 11 No. 1, Issue of January 15, 2008
© 2008 by Pontificia Universidad Católica de Valparaíso -- Chile Received February 20, 2007 / Accepted July 9, 2007
DOI: 10.2225/vol11-issue1-fulltext-8
RESEARCH ARTICLE

Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen

Vijay V. Gottemukkala
School of Pharmacy
University of Missouri-Kansas City
5100 Rockhill Road, Kansas City, MO
64110, United States
Tel: 1 816 582-9770
Fax: 1 410 877 9150
E-mail: vijayvarma555@hotmail.com

Kalyan K. Saripella
Philadelphia College of Pharmacy
University of the Sciences in Philadelphia
600 S. 43rd Street, Philadelphia, PA
19104, United States
Tel: 1 215 629 6534
Fax: 1 215 895 1161
E-mail: ksaripella@hotmail.com 

Anil K. Kadari
School of Pharmacy
University of Missouri-Kansas City
5100 Rockhill Road, Kansas City, MO
64110, United States
Tel: 1 816 916 8855
E-mail: anilkadari@gmail.com 

Steven H. Neau*
Department of Pharmaceutical Sciences
Philadelphia College of Pharmacy
University of the Sciences in Philadelphia
600 S. 43rd Street, Philadelphia, PA
19104, United States
Tel: 1 215 596 8825
Fax: 1 215 895 1161
E-mail: s.neau@usip.edu

*Corresponding author

Financial support: The NIH supported this research through grant GM061565-01 A2.

Keywords: enantioselective, esterification, ibuprofen, lipase, solvent-effect, water activity.

Abbreviations:

NSAIDs: non steroidal anti-inflammatory drugs

Abstract   Full Text
Abstract
Article
References

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.

Supported by UNESCO / MIRCEN network