A novel R-stereoselective amidase from Pseudomonas sp. MCI3434 acting on piperazine-2-tert-butylcarboxamide

European Journal of Biochemistry

Volumn 271, Issue 8, 2004, Pages 1580-1590

  Komeda, Hidenobu ^a   Harada, Hiroyuki ^a   Washika, Shingo ^a   Sakamoto, Takeshi ^b   Ueda, Makoto ^b   Asano, Yasuhisa ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b MITSUBISHI CHEMICAL CORPORATION   (Japan)

Author keywords

Amidase; Carboxamide; Hydrolysis; Piperazine 2 tert butyl; Pseudomonas sp.; Stereoselectivity

Indexed keywords

AMIDASE; AMIDE; BETA ALANINAMIDE; BETA UREIDOPROPIONASE; CADMIUM; CARBAMYLASE; CARBON NITROGEN HYDROLASE; CARBOXYLIC ACID DERIVATIVE; COBALT; COPPER ION; DEXTRO GLUTAMINAMIDE; ENZYME; GENOMIC DNA; LEAD; MANGANESE; MERCURY; N ETHYLMALEIMIDE; NICKEL; NITRILASE; PIPERAZINE 2 CARBOXAMIDE; PIPERAZINE 2 CARBOXYLIC ACID; PIPERAZINE 2 TERT BUTYLCARBOXAMIDE; PIPERAZINE DERIVATIVE; SILVER; UNCLASSIFIED DRUG; ZINC ION;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CONTROLLED STUDY; ELECTROPHORESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; GEL FILTRATION CHROMATOGRAPHY; GENE OVEREXPRESSION; GENE SEQUENCE; HYDROLYSIS; NONHUMAN; OPEN READING FRAME; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STEREOCHEMISTRY;

AMIDOHYDROLASES; AMINO ACID SEQUENCE; BLOTTING, SOUTHERN; CARBOXYLIC ACIDS; CONSERVED SEQUENCE; DNA PROBES; ESCHERICHIA COLI; HYDROLYSIS; MOLECULAR SEQUENCE DATA; PIPERAZINES; PSEUDOMONAS; RECOMBINANT PROTEINS; RESTRICTION MAPPING; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS PUTIDA; PSEUDOMONAS SP.;

EID: 2142757279     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.2004.04069.x     Document Type: Article

References (41)

1. Ambler, R.P., Auffret, A.D. & Clarke, P.H. (1987) The amino acid sequence of the aliphatic amidase from Pseudomonas aeruginosa. FEBS Lett. 215, 285-290.
2. Soubrier, F., Lévy-Schil, S., Mayaux, J.-F., Pétré, D., Arnaud, A. & Crouzet, J. (1992) Cloning and primary structure of the wide-spectrum amidases from Brevibacterium sp. R312: high homology to the amiE product from Pseudomonas aeruginosa. Gene 116, 99-104.
3. Skouloubris, S., Labigne, A. & Reuse, H.D. (1997) Identification and characterization of an aliphatic amidases in Helicobacter pylori. Mol. Microbiol. 25, 989-998.
4. Cheong, T.K. & Oriel, P.J. (2000) Cloning of a wide-spectrum amidase from Bacillus stearothermophilus BR388 in Escherichia coli and marked enhancement of amidase expression using directed evolution. Enzyme Microb. Technol. 26, 152-158.
5. Scorpio, A. & Zhang, Y. (1996) Mutations in pncA, a gene encoding pyrazinamidase/nicotinamidase, cause resistance to the antituberculous drug pyrazinamide in tubercle bacillus. Nat. Med. 2, 662-667.
6. Asano, Y. & Lübbehüsen, T.L. (2000) Enzymes acting on peptides containing D-amino acid. J. Biosci. Bioeng. 89, 295-306.
7. Kamphuis, J., Boesten, W.H.J., Broxterman, Q.B., Hermes, H.F.M., van Balken, J.A.M., Meijer, E.M. & Schoemaker, H.E. (1990) New developments in the chemoenzymatic production of amino acids. Adv. Biochem. Eng. Biotechnol. 42, 133-186.
8. Schmid, A., Dordick, J.S., Hauer, B., Kiener, A., Wubbolts, M. & Witholt, B. (2001) Industrial biocatalysis today and tomorrow. Nature 409, 258-268.
9. Mayaux, J.-F., Cerbelaud, E., Soubrier, F., Faucher, D. & Pétré, D. (1990) Purification, cloning, and primary structure of an enantiomer-selective amidases from Brevibacterium sp. strain R312: structural evidence for genetic coupling with nitrile hydratase. J. Bacteriol. 172, 6764-6773.
10. Ciskanik, L.M., Wilczek, J.M. & Fallon, R.D. (1995) Purification and characterization of an enantioselective amidases from Pseudomonas chlororaphis B23. Appl. Environ. Microbiol. 61, 998-1003.
11. Kobayashi, M., Komeda, H., Nagasawa, T., Nishiyama, M., Horinouchi, S., Beppu, T., Yamada, H. & Shimizu, S. (1993) Amidase coupled with low-molecular-mass nitrile hydratase from Rhodococcus rhodochrous J1: sequencing and expression of the gene and purification and characterization of the gene product. Eur. J. Biochem. 217, 327-336.
12. Trott, S., Bauer, R., Knackmuss, H.-J. & Stolz, A. (2001) Genetic and biochemical characterization of an enantioselective amidase from Agrobacterium tumefciens strain d3. Microbiology 147, 1815-1824.
13. Hayashi, T., Yamamoto, K., Matsuo, A., Otsubo, K., Muramatsu, S., Matsuda, A. & Komatsu, K. (1997) Characterization and cloning of an enantioselective amidase from Comamonas acidovorans KPO-2771-4. J. Ferment. Bioeng. 83, 139-145.
14. Hermes, H.F.M., Sonke, T., Peters, P.J.H., van Balken, J.A.M., Kamphuis, J., Dijkhuizen, L. & Meijer, E.M. (1993) Purification and characterization of an 1-aminopeptidase from Pseudomonas putida ATCC 12633. Appl. Environ. Microbiol. 59, 4330-4334.
15. van den Tweel, W.J.J., van Dooren, T.J.G.M., de Jonge, P.H., Kaptein, B., Duchateau, A.L.L. & Kamphuis, J. (1993) Ochrobactrum anthropi NCIMB 40321: a new biocatalyst with broadspectrum 1-specific amidases activity. Appl. Microbiol. Biotechnol. 39, 296-300.
16. Hermes, H.F.M., Tandler, R.F., Sonke, T., Dijkhuizen, L. & Meijer, E.M. (1994) Purification and characterization of an 1-amino amidase from Mycobacterium neoaurum ATCC 25795. Appl. Environ. Microbiol. 60, 153-159.
17. Komeda, H. & Asano, Y. (2000) Gene cloning, nucleotide sequencing, and purification and characterization of the D-stereospecific amino-acid amidase from Ochrobactrum anthropi SV3. Eur. J. Biochem. 267, 2028-2035.
18. Ozaki, A., Kawasaki, H.M., Yagasaki, M. & Hashimoto, Y. (1992) Enzymatic production of D-alanine from DL-alaninamide by novel D-alaninamide specific amide hydrolase. Biosci. Biotechn Biochem. 56, 1980-1984.
19. Baek, D.H., Kwon, S.-J., Hong, S.-P., Kwak, M.-S., Lee, M.-H., Song, J.J., Lee, S.-G., Yoon, K.-H. & Sung, M.-H. (2003) Characterization of a thermostable D-stereospecific alanine amidase from Brevibacillus borstelensis BCS-1. Appl. Environ. Microbiol. 69, 980-986.
20. Bigge, C.F., Johnson, G., Ortwine, D.F., Drummond, J.T., Retz, D.M., Brahce, L.J., Coughenour, L.L., Marcoux, F.W. & Probert, A.W. (1992) Exploration of N-phosphonoalkyl-, N-phosphonoalkenyl-, and N-(phosphonoalkyl) phenyl-spaced alpha-amino acids as competitive N-methyl-D-aspartic acid antagonists. J. Med. Chem. 35, 1371-1384.
21. Bruce, M.A., Laurent, D.R.S., Poindexter, G.S., Monkovic, I., Huang, S. & Balasubramanian, N. (1995) Kinetic resolution of piperazine-2-carboxamide by leucine aminopeptidase: an application in the synthesis of the nucleoside transport blocker (-)draflazine. Synthetic Commun. 25, 2673-2684.
22. Askin, D., Eng, K.K., Rossen, K., Purick, R.M., Wells, K.M., Volante, R.P. & Reider, P.J. (1994) Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (5)-glycidyl tosylate: synthesis of the orally active HIV-1 protease inhibitor L-735,524. Tetrahedron Lett. 35, 673-676.
23. Eichhorn, E., Roduit, J.-P., Shaw, N., Heinzmann, K. & Kiener, A. (1997) Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2- carboxylic acid, and (5)-piperizine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells. Tetrahed. Asymm. 8, 2533-2536.
24. Sambrook, J., Fritsch, E.F. & Maniatis, T. (1989) Molecular Cloning: a Laboratory Manual, 2nd edn. Cold Spring Harbor Laboratory, Cold Spring Harbor N.Y.
25. Misawa, N., Nakagawa, M., Kobayashi, K., Yamano, S., Izawa, Y., Nakamura, K. & Harashima, K. (1990) Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli. J. Bacteriol. 172, 6704-6712.
26. Inoue, H., Nojima, H. & Okayama, H. (1990) High efficiency transformation of Escherichia coli with plasmids. Gene 96, 23-28.
27. Sanger, F., Nicklen, S. & Coulson, A.R. (1977) DNA sequencing with chain-terminating inhibitors. Proc. Natl Acad. Sci. USA 74, 5463-5467.
28. Altschul, S.F., Gish, W., Miller, W., Myers, E.W. & Lipman, D.L. (1990) Basic local alignment search tool. J. Mol. Biol. 215, 403-410.
29. Bradford, M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
30. Fawcett, J.K. & Scott, J.E. (1960) A rapid and precise method for the determination of urea. J. Clin. Pathol. 13, 156-159.
31. Conway, E.J. & Byrne, A. (1933) An absorption apparatus for the microdetermination of certain volatile substances. I. The microdetermination of ammonia. Biochem. J. 27, 419-429.
32. Laemmli, U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
33. Stover, C.K., Pham, X.Q., Erwin, A.L., Mizoguchi, S.D., Warrener, P., Hickey, M.J., Brinkman, F.S., Hufnagle, W.O., Kowalik, D.J., Lagrou, M., Garber, R.L., Goltry, L., Tolentino, E., Westbrock-Wadman, S., Yuan, Y., Brody, L.L., Coulter, S.N., Folger, K.R., Kas, A., Larbig, K., Lim, R., Smith, K., Spencer, D., Wong, G.K., Wu, Z., Paulsen, I.T., Reizer, J., Saier, M.H., Hancock, R.E., Lory, S. & Olson, M.V. (2000) Complete genome sequence of Pseudomonas aeruginosa PA01, an opportunistic pathogen. Nature 406, 959-964.
34. Bentley, S.D., Chater, K.F., Cerdeno-Tarraga, A.M., Challis, G.L., Thomson, N.R., James, K.D., Harris, D.E., Quail, M.A., Kieser, H., Harper, D., Bateman, A., Brown, S., Chandra, G., Chen, C.W., Collins, M., Cronin, A., Fraser, A., Goble, A., Hidalgo, J., Hornsby, T., Howarth, S., Huang, C.H., Kieser, T., Larke, L., Murphy, L., Oliver, K., O'Neil, S., Rabbinowitsch, E., Rajandream, M.A., Rutherford, K., Rutter, S., Seeger, K., Saunders, D., Sharp, S., Squares, R., Squares, S., Taylor, K., Warren, T., Wietzorrek, A., Woodward, J., Barrell, B.G., Parkhill, J. & Hopwood, D.A. (2002) Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417, 141-147.
35. Schnider, U., Keel, C., Defago, G. & Haas, D. (1995) Tn5 directed cloning of pqq genes from Pseudomonas fluorescens CHA0: mutational inactivation of the genes results in overproduction of the antibiotic pyoluteorin. Appl. Environ. Microbiol. 61, 3856-3864.
36. Nelson, K.E., Weinel, C., Paulsen, I.T., Dodson, R.J., Hilbert, H., Martins dos Santos, V.A.P., Fouts, D.E., Gill, S.R., Pop, M., Holmes, M., Brinkac, L., Beanan, M., DeBoy, R.T., Daugherty, S., Kolonay, J., Madupu, R., Nelson, W., White, O., Peterson, J., Khouri, H., Hance, I., Chris Lee, P., Holtzapple, E., Scanlan, D., Tran, K., Moazzez, A., Utterback, T., Rizzo, M., Lee, K., Kosack, D., Moestl, D., Wedler, H., Lauber, J., Stjepandic, D., Hoheisel, J., Straetz, M., Heim, S., Kiewitz, C., Eisen, J., Timmis, K.N., Duesterhoeft, A., Tuemmler, B. & Fraser, C.M. (2002) Complete genome sequence and comparative analysis of the metabolically versatile Pseudomonas putida KT2440. Environ. Microbiol. 4, 799-808.
37. Capela, D., Barloy-Hubler, F., Gouzy, J., Bothe, G., Ampe, F., Batut, J., Boistard, P., Becker, A., Boutry, M., Cadieu, E., Dreano, S., Gloux, S., Godrie, T., Goffeau, A., Kahn, D., Kiss, E., Lelaure, V., Masuy, D., Pohl, T., Portetelle, D., Puhler, A., Purnelle, B., Ramsperger, U., Renard, C., Thebault, P., Vandenbol, M., Weidner, S. & Galibert, F. (2001) Analysis of the chromosome sequence of the legume symbiont Sinorhizobium meliloti strain 1021. Proc. Natl Acad. Sci. USA 98, 9877-9882.
38. Ikeda, H., Ishikawa, J., Hanamoto, A., Shinose, M., Kikuchi, H., Shiba, T., Sakaki, Y., Hattori, M. & Omura, S. (2003) Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis. Nat. Biotechnol. 21, 526-531.
39. Pace, H.C. & Brenner, C. (2001) The nitrilase superfamily: classification, structure and function. Genome Biol. 2, 1-9.
40. Askin, D., Eng, K.K., Reider, P. & Volante, R.P. (1996) Process to make HIV protease inhibitor from 2-(S)-4-picolyl-2-piperazine-t- butylcarboxamide. PCT/US96/02556.
41. Rosen, K., Weissman, S.A., Sager, J., Reamer, R.A., Askin, D., Volante, R.P. & Reider, P.J. (1995) Asymmetric hydrogenation of tetrahydropyrazines: synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir. Tetrahedron Lett. 36, 6419-6422.