Commercially viable resolution of ibuprofen

Biotechnology Journal

Volumn 4, Issue 8, 2009, Pages 1222-1224

  Chávez Flores, David ^a   Salvador, James M ^a  

^a UNIVERSITY OF TEXAS AT EL PASO   (United States)

Author keywords

Enantiomeric excess; Enantiomeric ratio; Esterify; Hydrolysis

Indexed keywords

BUTAN-1-OL; CANDIDA RUGOSA LIPASE; DECYL ALCOHOLS; ENANTIOMERIC EXCESS; ENANTIOMERIC RATIO; ENANTIOSELECTIVE ESTERIFICATION; ENANTIOSELECTIVE HYDROLYSIS; ENVIRONMENTALLY-FRIENDLY; ESTERIFY; IN-VITRO; NON-STEROIDAL ANTI-INFLAMMATORY DRUGS; PHOSPHATE BUFFERS; SIDE EFFECT;

ALKYLATION; DISTILLATION; ESTERIFICATION; ESTERS; HYDROLYSIS;

DRUG PRODUCTS;

IBUPROFEN;

ARTICLE; CANDIDA RUGOSA; CATALYSIS; DISTILLATION; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; IN VITRO STUDY; PRIORITY JOURNAL; SEPARATION TECHNIQUE;

ALCOHOLS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CANDIDA; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; CYCLOHEXANES; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTERS; HYDROLYSIS; IBUPROFEN; KINETICS; LIPASE; MODELS, CHEMICAL; PAIN; STEREOISOMERISM;

CANDIDA RUGOSA;

EID: 70350099219     PISSN: 18606768     EISSN: 18607314     Source Type: Journal    
DOI: 10.1002/biot.200900078     Document Type: Article

References (18)

1. Snell, D., Colby, J., Enantioselective hydrolysis of racemic ibuprofen amide to S-(+)-ibuprofen by Rhododcoccus AJ270. Enzyme Microb. Technol. 1999, 24, 160-163.
2. Chang, C.-S., Tsai, S.-W.m A facile enzymatic process for the preparation of (S)-Naproxen ester prodrug in organic solvents. Enzyme Microb. Technol. 1997, 20, 635-639.
3. Shen, T. Y., Perspective in nonsteriodal antiinflamatory agents. Angew. Chem. Int. Edn. Engl. 1972, 11, 460-472.
4. Adams, S.S., Bresloff, P., Manson, G.C., Pharmacological difference between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-) isomer. J. Pharmacol. 1976, 28, 156-157.
5. Fazlena, H., Kamaruddin, A. H., Zulkali, M. M. D., Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production. Bioprocess. Biosyst. Eng. 2006, 28, 227-233.
6. Mustranta, A., Use of lipases in the resolution of racemic ibuprofen. Appl. Microbiol. Biotechnol. 1992, 38, 61-66.
7. Chen, C.-S., Sih, C. J., General aspects and optimization of enantioselective biocatalysis in organic solvents. Angew. Chem. Int. Edn. Engl. 1989, 28, 695-707.
8. Bornscheuer, U. T., Kazlauskas, R. J., Hydrolases in Organic Synthesis. Wiley-VCH, Weinheim 1999.
9. Xin, J.-Y., Li, S.-B., Xu,Y., Chui, J.-R., Xia, C.-G., Dynamic enzymatic resolution of naproxen methyl ester in a membrane bioreactor. J. Chem. Technol. Biotechnol. 2001, 76, 579-585.
10. Chang, C.-S., Tsai, S.-W., Lipase-catalyzed dynamic resolution of naproxen thioester by thiotransesterification in isooctane. Biochem. Eng. J. 1999, 3, 239-242.
11. Lin, C.-N., Tsai, S.-W., Dynamic kinetic resolution of suprofen thioester via coupled trioctylamine and lipase catalysis. Biotechnol. Bioeng. 2000, 69, 31-38.
12. Ducret, A., Trani, M., Lortie, R., Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity. Enzyme Microb. Technol. 1998, 22, 212-216.
13. Jayasundar, J. J., Baddireddi, S. L., Venkateshamurthy, R., Mathuranthagam, J. A. et al., Insights from molecular dynamics simulations into pH-dependent enantioselective hydrolysis of ibuprofen esters by Candida rugosa lipase. Protein Eng. 2003, 16, 1017-1024.
14. Allenmark, S.G., Chromatographic Enantioseparation: Methods and Applications (2nd Edition). Stig Allenmark, Ellis Horwood Series in Analytical Chemistry, Ellis Horwood, New York 1991.
15. Satej, V. B, Steven, H. N., Lipase-catalyzed enantioselective esterification of flurbiprofen with n-butanol. Electron. J. Biotechnol. 2000, 3; ISSN: 0717-3458.
16. Tsai, S.-W., Lin, J.-J., Chang, C.-S., Chen, J.-P., Enzymatic synthesis of (S)-ibuprofen ester prodrug from racemic ibuprofen by lipase in organic solvents. Biotechnol. Prog. 1997, 13, 82-88.
17. Sanchez-Dominguez, M., Benoit, N., Pierre Krafft, M., Synthesis of triphilic, Y-shaped molecular surfactants. Tetrahedron 2008, 64, 522-528.
18. US Patent 5560926. Process for the production of an S-ibuprofen-containing tablet.