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.
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- Brown P. R., Smyth M. J., Clarke P. H., Rosemeyer M. A. The subunit structure of the aliphatic amidase from Pseudomonas aeruginosa. Eur J Biochem. 1973 Apr 2;34(1):177–187. doi: 10.1111/j.1432-1033.1973.tb02744.x. [DOI] [PubMed] [Google Scholar]
- Caldwell J., Hutt A. J., Fournel-Gigleux S. The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences. Biochem Pharmacol. 1988 Jan 1;37(1):105–114. doi: 10.1016/0006-2952(88)90762-9. [DOI] [PubMed] [Google Scholar]
- Chion C. K., Duran R., Arnaud A., Galzy P. N-terminal amino acid sequence of Brevibacterium sp. R312 wide-spectrum amidase. Appl Microbiol Biotechnol. 1991 Nov;36(2):205–207. doi: 10.1007/BF00164420. [DOI] [PubMed] [Google Scholar]
- Effenberger F., Böhme J. Enzyme-catalysed enantioselective hydrolysis of racemic naproxen nitrile. Bioorg Med Chem. 1994 Jul;2(7):715–721. doi: 10.1016/0968-0896(94)85022-4. [DOI] [PubMed] [Google Scholar]
- FAWCETT J. K., SCOTT J. E. A rapid and precise method for the determination of urea. J Clin Pathol. 1960 Mar;13:156–159. doi: 10.1136/jcp.13.2.156. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gilligan T., Yamada H., Nagasawa T. Production of S-(+)-2-phenylpropionic acid from (R,S)-2-phenylpropionitrile by the combination of nitrile hydratase and stereoselective amidase in Rhodococcus equi TG328. Appl Microbiol Biotechnol. 1993 Aug;39(6):720–725. doi: 10.1007/BF00164456. [DOI] [PubMed] [Google Scholar]
- LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
- Mayaux J. F., Cerbelaud E., Soubrier F., Yeh P., Blanche F., Pétré D. Purification, cloning, and primary structure of a new enantiomer-selective amidase from a Rhodococcus strain: structural evidence for a conserved genetic coupling with nitrile hydratase. J Bacteriol. 1991 Nov;173(21):6694–6704. doi: 10.1128/jb.173.21.6694-6704.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Nawaz M. S., Khan A. A., Seng J. E., Leakey J. E., Siitonen P. H., Cerniglia C. E. Purification and characterization of an amidase from an acrylamide-degrading Rhodococcus sp. Appl Environ Microbiol. 1994 Sep;60(9):3343–3348. doi: 10.1128/aem.60.9.3343-3348.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Weber K., Osborn M. The reliability of molecular weight determinations by dodecyl sulfate-polyacrylamide gel electrophoresis. J Biol Chem. 1969 Aug 25;244(16):4406–4412. [PubMed] [Google Scholar]
- Yamamoto K., Oishi K., Fujimatsu I., Komatsu K. Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750. Appl Environ Microbiol. 1991 Oct;57(10):3028–3032. doi: 10.1128/aem.57.10.3028-3032.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Yamamoto K., Ueno Y., Otsubo K., Kawakami K., Komatsu K. Production of S-(+)-ibuprofen from a nitrile compound by Acinetobacter sp. strain AK226. Appl Environ Microbiol. 1990 Oct;56(10):3125–3129. doi: 10.1128/aem.56.10.3125-3129.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]