Physiological relevance of successive hydroxylations of toluene by toluene para-monooxygenase of Ralstonia pickettii PKO1

Biocatalysis and Biotransformation

Volumn 22, Issue 4, 2004, Pages 283-289

  Fishman, Ayelet ^a   Tao, Ying ^a   Wood, Thomas K ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

Phenol hydroxylase; Toluene para monooxygenase toluene pathway

Indexed keywords

BENZENE; BIODEGRADATION; CELL CULTURE; ESCHERICHIA COLI; HYDROXYLATION; METHANOL; OXIDATION; SUBSTRATES;

DEGRADATION PATHWAYS; HYDROXYLASE; PRODUCT DISTRIBUTION; TOLUENE PARA-MONOOXYGENASE (TPMO);

TOLUENE;

4 METHYLCATECHOL; BACTERIAL ENZYME; META CRESOL; ORTHO CRESOL; OXYGENASE; PARA CRESOL; PHENOL DERIVATIVE; TOLUENE; TOLUENE 4 MONOOXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; CHEMICAL REACTION; ENZYME ACTIVITY; ENZYME DEGRADATION; ESCHERICHIA COLI; HYDROXYLATION; MICHAELIS MENTEN KINETICS; NONHUMAN; OPERON; OXIDATION; PROCESS OPTIMIZATION; PROTEIN EXPRESSION; RALSTONIA; RALSTONIA PICKETTII; SYNTHESIS;

ESCHERICHIA COLI; RALSTONIA PICKETTII;

EID: 11244252270     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/10242420400012008     Document Type: Article

References (34)

1. Arenghi, F.L.G., Berlanda, D., Galli, E., Sello, G. and Barbieri, P. (2001) Organization and regulation of meta cleavage pathway genes for toluene and o-xylene derivative degradation in Pseudomonas stutzeri OX1, Appl. Environ. Microbiol. 67, 3304-3308.
2. Arenghi, F.L.G., Pinti, M., Galli, E. and Barbieri, P. (1999) Identification of the Pseudomonas stutzeri OX1 toluene-o xylene monooxygenase regulatory gene (touR) and its cognate promoter, Appl. Environ. Microbiol. 65, 4057-4063.
3. Bertoni, G., Bolognese, F., Galli, E. and Barbieri, P. (1996) Cloning of the genes for and characterization of the early stages of toluene and o-xylene catabolism in Pseudomonas stutzeri OX1, Appl. Environ. Microbiol. 62, 3704-3711.
4. Bertoni, G., Martino, M., Galli, E. and Barbieri, P. (1998) Analysis of the gene cluster encoding toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1, Appl. Environ. Microbiol. 64, 3626-3632.
5. Burton, S.G. (2003) Oxidizing enzymes as biocatalysts, Trends Biotech. 21, 543-549.
6. Byrne, A.M., Kukor, J.J. and Olsen, R.H. (1995) Sequence analysis of the gene cluster encoding toluene-3-monooxygenase from Pseudomonas pickettii PKO1, Gene 154, 65-70.
7. Byrne, A.M. and Olsen, R.H. (1996) Cascade regulation of the toluene-3-monooxygenase operon (tbuA1UBVA2C) of Burkholderia pickettii PKO1: Role of the tbuA1 promoter (PtbuA1) in the expression of its cognate activator, TbuT, J. Bacteriol. 178, 6327-6337.
8. Cafaro, V., Izzo, V., Scognamiglio, R., Notomista, E., Capasso, P., Casbarra, A., Pucci, P. and Di Donato, A. (2004) Phenol hydroxylase and toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1: interplay between two enzymes, Appl. Environ. Microbiol. 70, 2211-2219.
9. Canada, K.A., Iwashita, S., Shim, H. and Wood, T.K. (2002) Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation, J. Bacteriol. 184, 344-349.
10. Fishman, A., Tao, Y., Bentley, W.E. and Wood, T.K. (2004a) Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene, Biotechnol. Bioeng. 87, 779-790.
11. Fishman, A., Tao, Y. and Wood, T.K. (2004b) Toluene 3-mono oxygenase of Ralstonia pickettii PKO1 is a para-hydroxylating enzyme, J. Bacteriol. 186, 3117-3123.
12. Johnson, G.R. and Olsen, R.H. (1995) Nucleotide sequence analysis of genes encoding a toluene/benzene-2-monooxygenase from Pseudomonas sp. strain JS150, Appl. Environ. Microbiol. 61, 3336-3346.
13. Johnson, G.R. and Olsen, R.H. (1997) Multiple pathways for toluene degadation in Burkholderia sp. strain JS150, Appl. Environ. Microbiol. 63, 4047-4052.
14. Kahng, H.-Y., Byrne, A.M., Olsen, R.H. and Kukor, J.J. (2000) Characterization and role of tbuX in utilization of toluene by Ralstonia pickettii PKO1, J. Bacteriol. 182, 1232-1242.
15. Kahng, H.-Y., Malinverni, J.C., Majko, M.M. and Kukor, J.J. (2001) Genetic and functional analysis of the tbc operons for catabolism of alkyl- and chloroaromatic compounds in Burkholderia sp. strain JS150, Appl. Environ. Microbiol. 67, 4805-4816.
16. Kukor, J.J. and Olsen, R.H. (1990) Molecular cloning, characterization, and regulation of a Pseudomonas pickettii PKO1 gene encoding phenol hydroxylase and expression of the gene in Pseudomonas aeruginosa PAO1c, J. Bacteriol. 172, 4624-4630.
17. Kukor, J.J. and Olsen, R.H. (1991) Genetic organization and regulation of a meta cleavage pathway for catechols produced from catabolism of toluene, benzene, phenol, and cresols by Pseudomonas pickettii PKO1, J. Bacteriol. 173, 4587-4594.
18. Kukor, J.J. and Olsen, R.H. (1992) Complete nucleotide sequence of tbuD, the gene encoding phenol/cresol hydroxylase from Pseudomonas pickettii PKO1, and functional analysis of the encoded enzyme, J. Bacteriol. 174, 6518-6526.
19. Kukor, J.J. and Olsen, R.H. (1996) Catechol 2,3-dioxygenases functional in oxygen-limited (hypoxic) environments, Appl. Environ. Microbiol. 62, 1728-1740.
20. Leahy, J.G., Byrne, A.M. and Olsen, R.H. (1996) Comparison of factors influencing trichloroethylene degradation by toluene-oxidizing bacteria, Appl. Environ. Microbiol. 62, 825-833.
21. Leahy, J.G., Johnson, G.R. and Olsen, R.H. (1997) Cross-regulation of toluene monooxygenases by the transcriptional activators TbmR and TbuT, Appl. Environ. Microbiol. 63, 3736-3739.
22. Notomista, E., Lahm, A., Di Donato, A. and Tramontano, A. (2003) Evolution of bacterial and archaeal multicomponent monooxygenases, J. Mol. Evol. 56, 435-445.
23. Olsen, R.H., Kukor, J.J., Byrne, A.M. and Johnson, G.R. (1997) Evidence for the evolution of a single component phenol/ cresol hydroxylase from a multicomponent toluene monooxygenase, J. Industr. Micro. Biotech. 19, 360-368.
24. Olsen, R.H., Kukor, J.J. and Kaphammer, B. (1994) A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1, J. Bacteriol. 176, 3749-3756.
25. Rui, L., Kwon, Y., Fishman, A., Reardon, K.F. and Wood, T.K. (2004a) Saturation mutagenesis of toluene ortho-monooxygenase of Burkholderia cepacia G4 for enhanced 1-naphthol synthesis and chloroform degradation, Appl. Environ. Microbiol. 70, 3246-3252.
26. Rui, L., Reardon, K.F. and Wood, T.K. (2004b) Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form indigoid compounds. Appl. Microbiol. Biotechnol., in press.
27. Sambrook, J., Fritsch, E.F. and Maniatis, T. (1989) Molecular cloning, a laboratory manual (Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY).
28. Schmid, A., Dordick, J.S., Hauer, B., Kiener, A., Wubbolts, M. and Witholt, B. (2001) Industrial biocatalysis today and tomorrow, Nature 409, 258-268.
29. Shim, H., Ryoo, D., Barbieri, P. and Wood, T.K. (2001) Aerobic degradation of mixtures of tetrachloroethylene, trichloroethylene, dichloroethtylenes, and vinyl chloride by toluene-o xylene monooxygenase of Pseudomonas stutzeri OX1, Appl. Microbiol. Biotechnol. 56, 265-269.
30. Tao, Y., Fishman, A., Bentley, W.E. and Wood, T.K. (2004a) Oxidation of benzene to phenol, catechol, and 1,2,3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1, Appl. Environ. Microbiol. 70, 3814-3820.
31. Tao, Y., Fishman, A., Bentley, W.E. and Wood, T.K. (2004b) Saturation mutagenesis of toluene 4-monooxygenase from Pseudomonas mendocina KR1 for the production of 3-methoxy catechol, methoxyhydroquinone, and methylhydroquinone, J. Bacteriol. 186, 4705-4713.
32. van Beilen, J.B., Duetz, W.A., Schmid, A. and Witholt, B. (2003) Practical issues in the application of oxygenases, Trends Biotech. 21, 170-177.
33. Vardar, G. and Wood, T.K. (2004) Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing of 4-methylresorcinol, methyhydroquinone, and pyrogallol, Appl. Environ. Microbiol. 70, 3253-3262.
34. Whited, G.M. and Gibson, D.T. (1991) Separation and partial characterization of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1, J. Bacteriol. 173, 3017-3020.