Characterization and cloning of an enantioselective amidase from Comamonas acidovorans KPO-2771-4

Journal of Fermentation and Bioengineering

Volumn 83, Issue 2, 1997, Pages 139-145

  Hayashi, Takahiko ^a   Yamamoto, Keizou ^b   Matsuo, Akira ^a   Otsubo, Kazumasa ^a   Muramatsu, Shuuji ^a   Matsuda, Akio ^a   Komatsu, Ken Ichi ^a  

^a ASAHI CHEMICAL INDUSTRY CO   (Japan)

^b NOGUCHI INSTITUTE   (Japan)

Author keywords

amidase; amide; Comamonas acidovorans; enantioselective; ketoprofen

Indexed keywords

AMINO ACIDS; CATALYST ACTIVITY; CLONING; DNA SEQUENCES; FILTRATION; HYDROLYSIS; PH EFFECTS; POLYPEPTIDES;

COMAMONAS ACIDOVORANS; ENANTIOSELECTIVE AMIDASE; KETOFREN;

ENZYMES;

2 (3' BENZOYLPHENYL)PROPIONAMIDE KETOPROFEN AMIDE; 4 CHLOROMERCURIBENZOIC ACID; AMIDASE; ARYLPROPIONIC ACID DERIVATIVE; NAPROXEN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME SPECIFICITY; NONHUMAN; PH; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION; TEMPERATURE;

BREVIBACTERIUM SP.; COMAMONAS; DELFTIA ACIDOVORANS; PSEUDOMONAS; PSEUDOMONAS SP.; RHODOCOCCUS SP.;

EID: 0030978217     PISSN: 0922338X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0922-338X(97)83572-6     Document Type: Article

References (23)

1. Caldwell, J., Hutt, A., and Fournel-Gigleux, S.: The metabolic chiral investigation and dispositional enantioselectivity of the 2-aryl propionic acids and their biological consequences. Biochem. Pharmacol., 37, 105-114 (1988).
2. Yamamoto, K., Oishi, K., Fujimatsu, I., and Komatsn, K.: Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750. Appl. Environ. Microbiol., 57, 3028-3022 (1991).
3. Yamamoto, K., Ueno, Y., Otsubo, K., Kawakami, K., and Komatsu, K.: Production of S-(+)-ibuprofen from a nitrile compound by Acinetobacter sp. strain AK226. Appl. Environ. Microbiol., 56, 3125-3129 (1990).
4. Beard, T., Cohen, M. A., Parratt, J. S., Tuner, N. J., Crosby, J., and Moilliot, J.: Stereoselective hydrolysis of nitriles and amides under mild conditions using a whole cell catalyst. Tetrahedron: Asymmetry, 4, 1085-1104 (1993).
5. Effenberger, F. and Bohme, J.: Enzyme-catalyzed enantioselective hydrolysis of racemic naproxen nitrile. Bioorg. Med. Chem., 7, 715-721 (1994).
6. Yamamoto, K., Otsubo, K., Matsuo, A, Hayashi, T., Fujimatsu, I., and Komatsu K.: Production of R-(-)-ketoprofen from an amide compound by Comamonas acidovorans KPO-2771-4. Appl. Environ. Microbiol., 62, 152-155 (1996).
7. Fawcett, J. K. and Scott, J. E.: A rapid and precise method for the determination of urea. J. Clin. Pathol., 13, 156-169 (1960).
8. Soubrier, F., Levy-Schil, Mayaux, J. F., Petre, D., Arnaud, A., and Crouzet, J.: Cloning and primary structure of the wide-spectrum amidase from Brevibacterium sp. R312: high homology to the amiE product from Pseudomonas aeruginosa. Gene, 116, 99-104 (1992).
9. Denefle, P., Kavarik, S., Guitton, J. D., Cartwright, T., and Mayaux, J. F.: Chemical synthesis of a gene coding for human angiogenin, its expression in Escherichia coli. and conversion of the product into its active form. Gene, 56, 61-70 (1987).
10. Mayaux, J. F., Cerbelaud, E., Soubrier, F., Faucher, D., and Petre, D.: Purification, cloning, and primary structure of an enantiomer-selective amidase from Brevibacterium sp. strain R312: evidence for genetic coupling with nitrile hydratase. J. Bacteriol., 172, 6764-6773 (1990).
11. Yanisch-Perron, C., Vieira, J., and Messing, J.: Improved M13 pharge vectors and host strains: nucleotide sequences of the M13mp18 and pUC19 vectors. Gene, 33, 103-119 (1985).
12. Saito, H. and Miura, K.: Preparation of transforming deoxyribonucleic acid by phenol treatment. Biochim. Biophys. Acta, 72, 619-629 (1963).
13. Ciora, T., Denefile, P., and Mayaux, J. F.: Rapid one-step automated sequencing reactions for 16 DNA samples using Taq polymerase and fluorescent primers. Nucl. Acids Res., 19, 188 (1991).
14. Bibb, M. J., Findlay, P. R., and Johnson, M. W.: The relationship between base composition and codon usage in bacterial gene and its use for the simple and reliable identification of protein-coding sequences. Gene, 30, 157-166 (1984).
15. Mayaux, J. F., Cerbelaud, E., Soubrier, F., Yeh, P., Branche, F., and Petre, 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., 173, 6694-6704 (1991).
16. Kobayashi, M., Komeda, H., Nagasawa, T., Nihiyama, M., Horinouchi, S., Beppu, T., Yamada, H., and Shimizu, S.: Amidase coupled with low-molecular-mass nitrile hydratase from Rhodococcus J1. Sequencing and expression of the gene and purification and characterization of the gene product. Eur. J. Biochem., 217, 327-336 (1993).
17. Hashimoto, Y., Nishiyama, M., Ikehata, O., Horinouchi, S., and Beppu, T.: Cloning and characterization of an amidase gene from Rhodococcus species N-774 and its expression in Escherichia coli. Biochem. Biophys. Acta, 1088, 225-233 (1991).
18. Nishiyama, M., Horinouchi, S., Kobayashi, M., Nagasawa, T., Yamada, H., and Beppu, T.: Cloning and characterization of gene responsible for metabolism of nitrile compounds from Pseudomonas chlororaphis B23. J. Bacteriol., 173, 2465-2472 (1991).
19. Ciskanik, L. M., Wilczek, J. M., and Fallen, R. D.: Purification and characterization of an enantioselective amidase from Pseudomonas chlororaphis B23. Appl. Environ. Microbiol., 61, 998-1003 (1995).
20. Thiery, A., Maestracci, M., Arnaud, A., Galzy, P., and Nicolas, M.: Purification and properties of an acylamide amidohydrolase (EC 3.5.1.4) with a wide spectrum from Brevibacterium sp. R312. J. Basic Microbiol., 5, 299-311 (1986).
21. Asano, Y., Nakazawa, A., Kato, Y., and Kondo, K.: Properties of a novel D-stereospecific aminopeptidase from Ochrobactrum anthropi. J. Biol. Chem., 264, 14233-14239 (1989).
22. Asano, Y., Mori, T., Hanamoto, S., Kalo, V., and Nakazawa, A.: A new D-stereospecific amino acid amidase from Ochrobactrum anthropi. Biochem. Biophys. Res. Commun., 162, 470-474 (1989).
23. Brammer, W. J., Charles, I. G., Matfield, M., Cheng-Pin, L., Drew, R. E., and Clarke, P. H.: The nucleotide sequence of the amiE gene of Pseudomonas aeruginosa. FEBS Lett., 215, 291-294 (1987).