Convenient lipase-assisted preparation of both enantiomers of suprofen, a non-steroidal anti-inflammatory drug

Chirality

Volumn 8, Issue 5, 1996, Pages 377-380

  Mertoli, Patrizia ^a   Nicolosi, Giovanni ^a   Patti, Angela ^a   Piattelli, Mario ^a  

^a CNR   (Italy)

Author keywords

Candida antarctica lipase; esterification; Mucor miehei lipase; NSAIDs; resolution

Indexed keywords

NONSTEROID ANTIINFLAMMATORY AGENT; SUPROFEN; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; OPTICAL RESOLUTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0029855417     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:5<377::AID-CHIR4>3.0.CO;2-B     Document Type: Article

References (9)

1. Klibanov, A.M. Asymmetric transformations catalysed by enzymes in organic solvents Acc. Chem. Res. 23:114-120, 1990 and references cited therein.
2. Tsai, S-W., Wei, H.-J. Enantioselective esterification of racemic naproxen in organic solvent. Enzyme Microb. Technol. 16:328-333, 1994.
3. Mustranta, A. Use of lipases in the resolution of racemic ibuprofen. Appl. Microbiol. Biotechnol. 38:61-66, 1992.
4. Morrone R, Nicolosi, G., Patti, A., Piattelli, M. Resolution of racemic flurbiprofen by lipase-mediated esterification in organic solvent. Tetrahedron: Asymmetry 6:1773-1778, 1995.
5. Ghislandi, V., La Manna, A., Azzolina, O., Gazzaniga, A., Vercesi, D. Configurational relationships in antiphlogistic hydratropic acids. II Farmaco 37:81-93, 1982.
6. Arroyo, M., Sinisterra, J.V. High enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized lipase from Candida antarctica: A mechanist approach. J. Org. Chem. 59:4410-4417, 1994.
7. Chen, C.-H., Fujimoto, Y., Girdaukas, G., Sih, C.J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104:7294-7299, 1982.
8. Brune, K., Beck, W.S., Geisslinger, G., Menzel-Soglowek, S. Peskar, B.M., Peskar, B.A. Aspirin-like drugs may block pain independently of prostaglandin synthesis inhibition. Experientia 47:257-261, 1991.
9. Hansch, C. Leo A. Substituent Constant for Correlation Analysis in Chemistry and Biology, New York: John Wiley and Sons, 1979.