Production of R-(-)-Ketoprofen from an Amide Compound by Comamonas acidovorans KPO-2771-4.

Applied and Environmental Microbiology
K YamamotoK Komatsu

Abstract

R-(-)-2-(3(prm1)-Benzoylphenyl)propionic acid [R-(-)-ketoprofen] was produced from racemic 2-(3(prm1)-benzoylphenyl)propionamide (keto-amide) by the isolated bacterial strain Comamonas acidovorans KPO-2771-4. Sodium fumarate as the carbon source and 2-azacyclononanone or isobutyronitrile as the enhancer in the culture medium were effective for bacterial growth and the enhancement of R-(-)-ketoprofen-producing activity. R-(-)-Ketoprofen produced from the keto-amide by resting cells was present in 99% enantiomeric exess. C. acidovorans KPO-2771-4 has an R-enantioselective amidase for keto-amide because the purified amidase from the bacterium hydrolyzed keto-amide, producing optically pure R-ketoprofen and ammonia.

References

Nov 1, 1991·Applied Microbiology and Biotechnology·C K ChionP Galzy
Oct 1, 1991·Applied and Environmental Microbiology·K YamamotoK Komatsu
Oct 1, 1990·Applied and Environmental Microbiology·K YamamotoK Komatsu
Apr 2, 1973·European Journal of Biochemistry·P R BrownM A Rosemeyer
Jul 1, 1994·Bioorganic & Medicinal Chemistry·F Effenberger, J Böhme
Sep 1, 1994·Applied and Environmental Microbiology·M S NawazC E Cerniglia
Mar 1, 1960·Journal of Clinical Pathology·J K FAWCETT, J E SCOTT

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