Enantioselective esterification of naproxen in aot/isooctane reversed micelles by lipase

Journal of the Chinese Institute of Chemical Engineers

Volumn 27, Issue 3, 1996, Pages

  Tsai, Shau Wei ^a   Lu, Chien Cheng ^a   Chang, Chun Sheng ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

Esterification; Lipase; Naproxen; Reversed Micelles

Indexed keywords

DRUG PRODUCTS; ENZYMES; ESTERS; MICELLES; MOLECULES; ORGANIC SOLVENTS; PARAFFINS; REACTION KINETICS; SOLUBILITY; SURFACE ACTIVE AGENTS; SUSPENSIONS (FLUIDS); WATER;

BISETHYLHEXYL SODIUM SULFOSUCCINATE; ENANTIOSELECTIVE ESTERIFICATION; ISOOCTANE; LIPASE; NAPROXEN; REVERSED MICELLES;

ESTERIFICATION;

EID: 0030145158     PISSN: 03681653     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. Battistel, E., D. Bianchi, P. Cesti and C. Pina, "Enzyme Resolution of (S)-(+)-Naproxen in a Continuous Reactor", Biotechnol. Bioeng., 38, 659 (1991).
2. Brown, E.D., R.Y. Yada and A.G. Marangori, "The Dependence of the Lipolytic Activity of Rhizopus arrhizus Lipase on Surfactant Concentration in Aerosol-OT/Isooctane Reversed Micelles and Its Relationship to Enzyme Structure", Biochem. Biophys. Acid, 1161, 66 (1993).
3. Gu, Q.M., C.S. Chen and C.J. Sih, "A Facile Enzymatic Resolution Process for the Preparation of (+)-S-2(Methoxy-2-naphthyl)propionic Acids (Naproxen)", Tetrahedron Lett., 27, 1763 (1986).
4. Hedstrom, G., J.P. Slotte, M. Backlund, O. Molander and J.B. Rosenholu, "Lipase-Catalyzed Synthesis and Hydrolysis of Cholesterol Oleate in AOT/Isooctane Microemulsions", Biocatalysis, 6, 281 (1992).
5. Hedstrom, G., M. Backlund and J.P. Slotte, "Enantioselective Synthesis of Ibuprofen Esters in AOT/Isooctane Microemulsions by Candida cylindracea Lipase", Biotechnol. and Bioeng., 42, 618 (1993).
6. Hernaiz, M.J., J.M. Sanchez-Montero and J.V. Sinisterra, "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, 10749 (1994).
7. Hutt, A.J. and J. Caldwell, "The Importance of Stereochemistry in the Clinical Pharmacokinetics of the 2-Arylpropionic Acid Non-Steroidal Anti-Inflammatory Drugs", Clin. Pharmacokin., 9, 371 (1984).
8. Marangoni, A.G., "Effects of the Interaction of Porcine Pancreatic Lipase with AOT/Isooctane Reversed Micelles on Enzyme Structure and Function Follow Predictable Patterns", Enzyme Microb. Technol., 15, 944 (1993).
9. Margolin, A.L., "Enzymes in the Synthesis of Chiral Drugs", Enzyme Microb. Technol., 15, 266 (1993).
10. Prazeres, D.M.F., F.A.P. Garcia and J.M.S. Cabral, "Kinetics and Stability of a Chromobacterium viscosum Lipase in Reversed Micellar and Aqueous Media", J. Chem. Tech. Biotechnol., 53, 159 (1992).
11. Sonawane, R.H., N.S. Bellur and J.R. Ahuja, "Recent Developments in the Synthesis of Optically Active 2-Arylpropionic Acids: An Important Class of Non-Steroidal Anti-Inflammatory Agents", Tetrahedron: Asymmetry, 3, 163 (1992).
12. Tsai, S.W. and H.J. Wei, "Kinetics of Enantioselective Esterification of Naproxen by Lipase in Organic Solvents", Biocatalysis, 11, 33 (1994a).
13. Tsai, S.W. and H.J. Wei, "Enantioselective Esterification of Racemic Naproxen by Lipases in Organic Solvent", Enzyme Microb. Technol., 16, 328 (1994b).
14. Tsai, S.W. and H.J. Wei, "Effect of Solvent on Enantioselective Esterification of Naporoxen by Lipase with Trimethylsilyl Methanol", Biotechnol. Bioeng., 43, 64 (1994c).
15. Tsai, S.W., K.P. Lee and C.L. Chiang, "Surfactant Effects on Lipase-Catalyzed Hydrolysis of Olive Oil in AOT/Isooctane Reversed Micelles", Biocatalysis and Biotransformation, 13, 89 (1995).
16. Tsai, S.W., C.C. Lu and C.S. Chang, "Surfactant Enhancement of (S)-Naproxen Ester Productivity from Racemic Naproxen by Lipase in Isooctane", Biotechncl. Bioeng., in press (1996).
17. Walde, P., D. Han and P.L. Luisi, "Spectroscopic and Kinetic Studies of Lipase Solubilized in Reversed Micelles", Biochemistry, 32, 4029 (1993).