Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents

Journal of Chemical Technology and Biotechnology

Volumn 65, Issue 2, 1996, Pages 156-162

  Tsai, Shau Wei ^a   Liu, Bih Yuan ^a   Chang, Chun Sheng ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

Esterification; Lipase; Naproxen; Organic mixture

Indexed keywords

NAPROXEN; ORGANIC SOLVENT; TOLUENE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; ESTERIFICATION; HYDROPHOBICITY; KINETICS;

EID: 0029671389     PISSN: 02682575     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-4660(199602)65:2<156::AID-JCTB415>3.0.CO;2-F     Document Type: Article

References (24)

1. Stinson, S. C., Chiral Drugs. C&EN, September 28 (1993) 46-76.
2. Margolin, A. L., Enzymes in the synthesis of chiral drugs. Enzyme Microb. Technol., 15 (1993) 266-80.
3. Hutt, A. J. & Caldwell, J., The importance of stereochemistry in the clinical pharmacokinetics of the 2-arylpropionic acid non-steroidal anti-inflammatory drugs. Clin. Pharmacokin., 9 (1984) 371-3.
4. Sonawane, R. H., Bellur, N. S. & Ahuja, J. R., Recent developments in the synthesis of optically active 2-arylpropionic acids: an important class of non-steroidal anti-inflammatory agents. Tetrahedron: Asymmetry, 3 (1992) 163-92.
5. Chan, A. S. C., A new route to important chiral drugs. CHEMTECH, March (1993) 46-51.
6. Ernst, F., Davide, P. & Hans, Z., Method for resolving racemic 6-methoxyl-alpha-methyl-2-naphthalene acetic acid into its enantiomers and resolving medium. European Patent Application EP 007116, 1980.
7. Vinzenzo, C. & Giancario, T., A new process for the optical resolution of racemic mixtures of alpha-naphthylpropionic acids. European Patent Application EP 143371, 1985.
8. Bojarski, J., Chromatography of enantiomers of 2-arylpropionic acids. J. Liq. Chromatogr., 12 (1989) 2685-706.
9. Pirkle, W. H., Welch, C. J. & Lamm B., Design, synthesis, and evaluation of an improved enantioselective Naproxen sector. J. Org. Chem., 57 (1992) 3854-60.
10. Cesti, P. & Piccardi, P., Process for the biotechnological preparation of optically active 2-arylalkanoic acids. European Patent Application EP 195717, 1986.
11. Gu, Q. M., Chen, C. S. & Sih, C. J., A facile enzymatic resolution process for the preparation of (+)-S-2-(6-methoxy-2-naphthyl)propionic acids (Naproxen). Tetrahedron Lett., 27 (1986) 1763-6.
12. Sih, C. J., Process for preparation of (S)-2-methylarylacetic acids. European Patent Application EP 227087, 1987.
13. Sih, C. J., Gu, Q. M., Fuelling, G., Wu, S. H. & Reddy, D. R., The use of microbial enzymes for the synthesis of optically active pharmaceuticals. Dev. Ind. Microbiol., 29 (1988) 221-9.
14. Battistel, E., Bianchi, D., Cesti, P. & Pina, C., Enzymatic resolution of (S)-(+)-Naproxen in a continuous reactor. Biotechnol. Bioeng., 38 (1991) 659-64.
15. Hernaiz, M. J., Sanchez-Montero, J. M. & Sinisterra, J. V., Comparison of the activity of commercial and semipurified lipase of Candida cylindracea in the hydrolysis of ester of (R, S) 2-aryl propionic acids. Tetrahedron, 50 (1994) 10749-60.
16. Mustranta, A., Use of lipases in the resolution of racemic ibuprofen. Appl. Microbiol. Biotechnol., 38 (1992) 61-6.
17. Hedstrom, G., Backlund, M. & Slotte, J. P., Enantioselective synthesis of ibuprofen esters in AOT/isooctane microemulsions by Candida cylindracea lipase. Biotechnol. Bioeng., 42 (1993) 618-24.
18. Arroyo, A. & Sinisterra, J. V., High enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized lipase from Candida antarctica: a mechanistic approach. J. Org. Chem., 59 (1994) 4410-17.
19. Tsai, S. W. & Wei, H. J., Enantioselective esterification of racemic Naproxen by lipases in organic solvent. Enzyme Microb. Technol., 16 (1994) 328-33.
20. Tsai, S. W. & Wei, H. J., Effect of solvent on enantioselective esterification of Naproxen by lipase with trimethylsilyl methanol. Biotechnol. Bioeng., 43 (1994) 64-8.
21. Tsai, S. W. & Wei, H. J., Kinetics of enantioselective esterification of Naproxen by lipase in organic solvents. Biocatalysis, 11 (1994) 33-45.
22. Tsai, S. W. & Wei, H. J., Self-normalized analysis of lipase-catalyzed conversion of Naproxen enantiomers. J. Liq. Chromatogr., 16 (1993) 2993-3001.
23. Parida, S. & Dordick, J. S., Substrate structure and solvent hydrophobicity control lipase catalysis and enantioselectivity in organic media. J. Am. Chem. Soc., 113 (1991) 2253-9.
24. Holmberg, E. & Huit, K., Application induced reversal of enantioselectivity in a lipase catalyzed resolution of 2-chloropropionic acid. Biocatalysis, 5 (1992) 289-96.