Purification and properties of 2-hydroxy-6-oxo-6(2′-aminophenyl)hexa-2,4-dienoic acid hydrolase involved in microbial degradation of carbazole

Protein Expression and Purification

Volumn 28, Issue 1, 2003, Pages 182-189

  Riddle, Robert R ^a   Gibbs, Phillip R ^b   Willson, Richard C ^a,b   Benedik, Michael J ^a  

^a University of Houston   (United States)

^b University of Houston   (United States)

Author keywords

Carbazole; HOPDA; Hydrolase; Meta Cleavage enzyme; Pseudomonas

Indexed keywords

ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS PUTIDA; PSEUDOMONAS SP.;

EID: 0345381843     PISSN: 10465928     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1046-5928(02)00676-9     Document Type: Article

References (30)

1. J.C. Arcos, M.F. Argus, Molecular geometry and carcinogenic activity of aromatic compounds. New perspectives, Adv. Cancer Res. 11 (1968) 305-471.
2. R.J. Grosser, D. Warshawsky, J.R. Vestal, Indigenous and enhanced mineralization of pyrene, benzo[a]pyrene, and carbazole in soils, Appl. Environ. Microbiol. 57 (1991) 3462-3469.
3. T. Kobayashi, R. Kurane, K. Nakajima, Y. Nakamura, K. Kirimura, S. Usami, Isolation of bacteria degrading carbazole under microaerobic conditions, i.e. nitrogen gas substituted conditions, Biosci. Biotechnol. Biochem. 59 (1995) 932-933.
4. L.M. Gieg, A. Otter, P.M. Fedorak, Carbazole degradation by Pseudomonas sp. LD2: metabolic characteristics and the identification of some metabolites, Environ. Sci. Technol. 30 (1996) 575-585.
5. S.I. Sato, J.W. Nam, K. Kasuga, H. Nojiri, H. Yamane H, T. Omori, Identification and characterization of genes encoding carbazole 1,9a-dioxygenase in Pseudomonas sp. strain CA10, J. Bacteriol. 179 (1997) 4850-4858.
6. S.I. Sato, N. Ouchiyama, T. Kimura, H. Nojiri, H. Yamane, T. Omori, Cloning of genes involved in carbazole degradation of Pseudomonas sp. strain CA10: nucleotide sequences of genes and characterization of meta-cleavage enzymes and hydrolase, J. Bacteriol. 179 (1997) 4841-4849.
7. J.M. Horn, S. Harayama, K.N Timmis, DNA sequence determination of the TOL plasmid (pWWO) xylGFJ genes of Pseudomonas putida: implications for the evolution of aromatic catabolism, Mol. Microbiol. 5 (1991) 2459-2474.
8. N. Hayase, K. Taira, K. Furukawa, Pseudomonas putida KF715 bphABCD operon encoding biphenyl and polychlorinated biphenyl degradation: cloning, analysis, and expression in soil bacteria, J. Bacteriol. 172 (1990) 1160-1164.
9. I. Nordlund, V. Shingler, Nucleotide sequences of the metacleavage pathway enzymes 2-hydroxymuconic semialdehyde dehydrogenase and 2-hydroxymuconic semialdehyde hydrolase from Pseudomonas CF600, Biochem. Biophys. Acta 1049 (1990) 227-230.
10. F.M. Menn, G.J. Zylstra, D.T. Gibson, Location and sequence of the todF gene encoding 2-hydroxy-6-oxohepta-2,4-dienoate hydrolase in Pseudomonas putida F1, Gene 104 (1991) 91-94.
11. B. Hofer, L.D. Eltis, D.N. Dowling, K.N. Timmis, Genetic analysis of a Pseudomonas locus encoding a pathway for biphenyl/polychlorinated biphenyl degradation, Gene 130 (1993) 47-55.
12. K. Furukawa, J. Hirose, A. Suyama, T. Zaiki, S. Hayashida, Gene components responsible for discrete substrate specificity in the metabolism of biphenyl (bph operon) and toluene (tod operon), J. Bacteriol. 175 (1993) 5224-5232.
13. D.L. Ollis, E. Cheah, M. Cygler, B. Dijkstra, F. Frolow, S.M. Franken, M. Harel, S.J. Remington, I. Silman, J. Schrag, The α/β hydrolase fold, Protein Eng. 5 (1992) 197-211.
14. R.C. Bayly, D. di Berardino, Purification and properties of 2-hydroxy-6-oxo-2,4-heptadienoate hydrolase from two strains of Pseudomonas putida, J. Bacteriol. 134 (1978) 30-37.
15. W.W. Lam, T.D. Bugg, Purification, characterization, and stereochemical analysis of a C-C hydrolase: 2-hydroxy-6-ketonona-2,4-diene-1,9-dioic acid 5,6-hydrolase, Biochemistry 36 (1997) 12242-12251.
16. I.M. Henderson, T.D. Bugg, Pre-steady-state kinetic analysis of 2-hydroxy-6-keto-nona-2,4-diene-1,9-dioic acid 5,6-hydrolase: kinetic evidence for enol/keto tautomerization, Biochemistry 36 (1997) 12252-12258.
17. R. Riddle, P.R. Gibbs, R.C. Willson, M.J. Benedik, Dioxygenase modification of carbazole for enhanced petroleum processing, J. Ind. Microbiol. Biotech. (2002), in press.
18. F.W. Studier, B.A. Moffatt, Use of bacteriophage T7 RNA polymerase to direct selective high-level expression of cloned genes, J. Mol. Biol. 189 (1986) 113-130.
19. M.A. Schell, Cloning and expression in Escherichia coli of the naphthalene degradation genes form plasmid NAH7, J. Bacteriol. 153 (1983) 822-829.
20. K. Kimbara, T. Hashimoto, M. Fukuda, T. Koana, M. Takagi, M. Oishi, K. Yano, Cloning and sequencing of two tandem genes involved in degradation of 2,3-dihydroxybiphenyl to benzoic acid in the polychlorinated biphenyl-degrading soil bacterium Pseudomonas sp. strain KKS102, J. Bacteriol. 171 (1989) 2740-2747.
21. E. Masai, K. Sugiyama, N. Iwashita, S. Shimizu, J.E. Hauschild, T. Hatta, K. Kimbara, K. Yano, M. Fukuda, The bphDEF metacleavage pathway genes involved in biphenyl/polychlorinated biphenyl degradation are located on a linear plasmid and separated from the initial bphACB genes in Rhodococcus sp. strain RHA1, Gene 187 (1997) 141-149.
22. D. Ahmad, J. Fraser, M. Sylvestre, A. Larose, A. Khan, J. Bergeron, J.M. Juneau, M. Sondossi, Sequence of the bphD gene encoding 2-hydroxy-6-oxo-(phenyl/chlorophenyl)hexa-2,4-dienoic acid (HOP/cPDA) hydrolase involved in the biphenyl/polychlorinated biphenyl degradation pathway in Comamonas testosteroni: evidence suggesting involvement of Ser112 in catalytic activity, Gene 156 (1995) 69-74.
23. H. Habe, K. Kasuga, H. Nojiri, H. Yamane, T. Omori, Analysis of cumene (isopropylbenzene) degradation genes from Pseudomonas fluorescens IP01, Appl. Environ. Microbiol. 62 (1996) 4471-4477.
24. E. Diaz, K.N. Timmis, Identification of functional residues in a 2-hydroxymuconic seimialdehyde hydrolase, J. Biol. Chem. 270 (1995) 6403-6411.
25. S.Y. Seah, G. Terracina, J.T. Bolin, P. Riebel, V. Snieckus, L.D. Eltis, Purification and preliminary characterization of a serine hydrolase involved in the microbial degradation of polychlorinated biphenyls, J. Biol. Chem. 273 (1998) 22943-22949.
26. J.F. Davey, D.W. Ribbons, Metabolism of resorcinylic compounds by bacteria. Purification and properties of acetylpyruvate hydrolase from Pseudomonas putida 01, J. Biol. Chem. 250 (1975) 3826-3830.
27. P.V. Bunz, R. Falchetto, A.M. Cook, Purification of two isofunctional hydrolases (E.C. 3.7.1.8) in the degradative pathway for dibenzofuran in Sphingomonas sp. strain RWI, Biodegradation 4 (1993) 171-178.
28. X. Peng, E. Masai, Y. Katayama, M. Fukuda, Characterization of the meta-cleavage compound hydrolase gene involved in degradation of the lignin-related biphenyl structure by Sphingomonas paucimobilis SYK-6, Appl. Environ. Microbiol. 65 (1999) 2789-2793.
29. M.L. Shuler, F. Kargi, in: Bioprocess Engineering Basic Concepts, second ed., Prentice-Hall, Upper Saddle River, NJ, 2002, pp. 69-73.
30. G. Hannig, S.C. Makrides, Strategies for optimizing heterologous protein expression in Escherichia coli, Tibtech 16 (1998) 54-60.