Lipase-catalyzed enantioselective esterification of flurbiprofen with n-butanol

Electronic Journal of Biotechnology

Volumn 3, Issue 3, 2000, Pages 195-201

  Bhandarkar, Satej V ^a   Neau, Steven H ^b  

^a Emisphere Technologies   (United States)

^b UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

Author keywords

Enantioselectivity; Esterification; Flurbiprofen; Lipase; Solvent dependence; Water activity

Indexed keywords

BUTANOL; FLURBIPROFEN;

BIOPROCESS; BIOTECHNOLOGICAL PRODUCTION; CATALYSIS; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ESTERIFICATION; HYDROPHOBICITY; MOLECULAR INTERACTION; PHYSICAL CHEMISTRY; RACEMIC MIXTURE; REACTION ANALYSIS; SOLVENT EFFECT; STRUCTURE ANALYSIS;

CANDIDA; CANDIDA RUGOSA; MUCOR; MUCOR JAVANICUS; SUIDAE;

EID: 0038753606     PISSN: 07173458     EISSN: None     Source Type: Journal    
DOI: 10.2225/vol3-issue3-fulltext-3     Document Type: Conference Paper

References (14)

1. Geisslinger, G., Menzel-Soglowek, S., Schuster, O. and Brune, K. (1992). Stereoselective high performance liquid chromatographic determination of flurbiprofen in human plasma. Journal of Chromatography 573:163-167.
2. Halling, P.J. (1992). Salt hydrates for water activity control with biocatalysts in organic media. Biotechnology Techniques 6:271-276.
3. Klibanov, A.M. (1990). Asymmetric transformations catalyzed by enzymes in organic solvents. Accounts of Chemical Research 23:114-120.
4. Laane, C., Boeren, S., Hilhorst, R. and Veeger, C. (1987). Optimization of biocatalysis in organic media. In: Laane, C., Tramper, J. and Lilly, M.D. eds. Biocatalysis in Organic Media. Elsevier Science Publishers, B. V., Amsterdam, The Netherlands, pp. 65-84.
5. Lotsch, J., Geisslinger, G., Mohammadian P., Brune, K. and Kobal, G. (1995). Effects of flurbiprofen enantiomers on pain-related chemosomatosensory evoked potentials in human subjects. British Journal of Clinical Pharmacology 40:339-346.
6. Mertoli, P., Nicolosi, G., Patti, A. and Piattelli, M. (1996). Convenient lipase-assisted preparation of both enantiomers of suprofen, a non-steroidal anti-inflammatory drug. Chirality 8:377-380.
7. Morrone, R., Nicolosi, G., Patti, A. and Piattelli, M. (1995). Resolution of racemic flurbiprofen by lipase-mediated esterification in organic solvent. Tetrahedron-Asymmetry 6:1773-1778.
8. Mustranta, A. (1992). Use of lipases in resolution of racemic ibuprofen. Applied Microbiology and Biotechnology 38:61-66.
9. Parida, S. and Dordick, J.S. (1993). Substrate structure and solvent hydrophobicity control lipase catalysis and enantioselectivity in organic media. Journal of the American Chemical Society 113:2253-2259.
10. Shen, T.Y. (1972). Perspectives in nonsteroidal antiinflammatory agents. Angewandte Chemie - International Edition in English 11:460-472.
11. Tsai, S.W., J.J. Lin, Chang, C.S. and Chen, J.P. (1997). Enzymatic synthesis of (S)-ibuprofen ester prodrug from racemic ibuprofen by lipase in organic solvents. Biotechnology Progress 13:82-88.
12. Tsai, S.W. and Wei, H.J. (1994). Enantioselective esterification of racemic naproxen in organic solvent. Enzyme and Microbial Technology 16:328-333.
13. Valivety, R.H., Halling, P.J., Peilow, A.D. and Macrae, A.R. (1992). Lipases from different sources vary widely in dependence of catalytic activity on water activity. Biochimica et Biophysica Acta 1122:143-146.
14. Wechter, W.J., Bigornia, A.E., Murray, E.D., Levine, B.H. and Young, J.W. (1993). Rac-flurbiprofen is more ulcerogenic than its (S)-enantiomer. Chirality 5:492-494.