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

Applied and Environmental Microbiology

Volumn 70, Issue 7, 2004, Pages 3814-3820

  Tao, Ying ^a   Fishman, Ayelet ^a   Bentley, William E ^b   Wood, Thomas K ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; CONCENTRATION (PROCESS); ENZYMES; ESCHERICHIA COLI; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; SYNTHESIS (CHEMICAL);

BACTERIAL METABOLIC PROCESSES; BIOLOGICAL CATALYSTS;

MICROBIOLOGY;

BACTERIAL PROTEIN; BENZENE; CATECHOL; PHENOL; PYROGALLOL; TOLUENE 2 MONOOXYGENASE; TOLUENE 3 MONOOXYGENASE; TOLUENE 4 MONOOXYGENASE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

MICROBIOLOGY;

ARTICLE; BACTERIAL METABOLISM; BURKHOLDERIA CEPACIA; BURKHOLDERIA CEPACIA G4; ESCHERICHIA COLI TG1 PBS(KAN); HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; LAC PROMOTER; MASS SPECTROMETRY; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PROMOTER REGION; PSEUDOMONAS; PSEUDOMONAS MENDOCINA KR1; RALSTONIA; RALSTONIA PICKETTII PKO1;

BASE SEQUENCE; BENZENE; CATECHOLS; DNA, BACTERIAL; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; OXYGENASES; PHENOL; PSEUDOMONAS MENDOCINA; PYROGALLOL; RALSTONIA;

BACTERIA (MICROORGANISMS); BURKHOLDERIA; BURKHOLDERIA CEPACIA; ESCHERICHIA COLI; NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS MENDOCINA; RALSTONIA; RALSTONIA PICKETTII;

EID: 3242763195     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.70.7.3814-3820.2004     Document Type: Article

References (37)

1. Azerad, R. 2001. Editorial overview: better enzyme for green chemistry. Curr. Opin. Biotechnol. 12:533-534.
2. Bertoni, G., F. Bolognese, E. Galli, and P. Barbieri. 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.
3. Bertoni, G., M. Martino, E. Galli, and P. Barbieri. 1998. Analysis of the gene cluster encoding toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1. Appl. Environ. Microbiol. 64:3626-3632.
4. Burton, S. G., A. Boshoff, W. Edwards, and P. D. Rose. 1998. Biotransformation of phenols using immobilised polyphenol oxidase. J. Mol. Catal. B Enzym. 5:411-416.
5. Byrne, A. M., J. J. Kukor, and R. H. Olsen. 1995. Sequence analysis of the gene cluster encoding toluene-3-monooxygenase from Pseudomonas pickettii PKO1. Gene 154:65-70.
6. Byrne, A. M., and R. H. Olsen. 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.
7. Canada, K. A., S. Iwashita, H. Shim, and T. K. Wood. 2002. Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation. J. Bacteriol. 184:344-349.
8. Chauhan, A., S. K. Samanta, and R. K. Jain. 2000. Degradation of 4-nitrocatechol by Burkholderia cepacia: a plasmid-encoded novel pathway. J. Appl. Microbiol. 88:764-772.
9. Dolfing, J., A. J. van den Wijngaard, and D. B. Janssen. 1993. Microbiological aspects of the removal of chlorinated hydrocarbons from air. Biodegradation 4:261-282.
10. Draths, K. M., and J. W. Frost. 1991. Conversion of D-glucose into catechol: the not-so-common pathway of aromatic biosynthesis. J. Am. Chem. Soc. 113:9361-9363.
11. Draths, K. M., and J. W. Frost. 1995. Environmentally compatible synthesis of catechol from D-glucose. J. Am. Chem. Soc. 117:2395-2400.
12. Fishman, A., Y. Tao, and T. K. Wood. 2004. Toluene 3-monooxygenase of Ralstonia pickettii is a para-hydroxylating enzyme. J. Bacteriol. 186:3117-3123.
13. Fujita, Y., I. Mori, K. Fujita, S. Kitano, and T. Tanaka. 1985. A color reaction of 1,2-diphenols based on colored complex formation with phenylfluorone and iron (III) and its application to the assay of catecholamines in pharmaceutical preparations. Chem. Pharm. Bull. 33:5385-5392.
14. Howe-Grant, M. (ed.). 1991. Kirk-Othmer encyclopedia of chemical technology, fourth ed., vol. 13. Wiley-Interscience Publishers, New York, N.Y.
15. Johnson, G. R., and R. H. Olsen. 1997. Multiple pathways for toluene degradation in Burkholderia sp. strain JS150. Appl. Environ. Microbiol. 63: 4047-4052.
16. Kadiyala, V., and J. C. Spain. 1998. A two-component monooxygenase catalyzes both the hydroxylation of p-nitrophenol and the oxidative release of nitrite from 4-nitrocatechol in Bacillus sphaericus JS905. Appl. Environ. Microbiol. 64:2479-2484.
17. Korte, J. E., I. Hertz-Picciotto, M. R. Schulz, L. M. Ball, and E. J. Duell. 2000. The contribution of benzene to smoking-induced leukemia. Environ. Health Perspect. 108:333-339.
18. Leahy, J. G., P. J. Batchelor, and S. M. Morcomb. 2003. Evolution of the soluble diiron monooxygenases. FEMS Microbiol. Rev. 27:449-479.
19. Leahy, J. G., G. R. Johnson, and R. H. Olsen. 1997. Cross-regulation of toluene monooxygenases by the transcriptional activators TbmR and TbuT. Appl. Environ. Microbiol. 63:3736-3739.
20. Luu, P. P., C. W. Yung, A. K. Sun, and T. K. Wood. 1995. Monitoring trichloroethylene mineralization by Pseudomonas cepacia G4 PR1. Appl. Microbiol. Biotechnol. 44:259-264.
21. Mitchell, K. H., J. M. Studts, and B. G. Fox. 2002. Combined participation of hydroxylase active site residues and effector protein binding in a para to ortho modulation of toluene 4-monooxygenase regiospecificity. Biochemistry 41:3176-3188.
22. Newman, L. M., and L. P. Wackett. 1995. Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. Biochemistry 34: 14066-14076.
23. Olsen, R. H., J. J. Kukor, and B. Kaphammer. 1994. A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1. J. Bacteriol. 176:3749-3756.
24. Oppenheim, S. F., J. M. Studts, B. G. Fox, and J. S. Dordick. 2001. Aromatic hydroxylation catalyzed by toluene 4-monooxygenase in organic solvent/aqueous buffer mixtures. Appl. Biochem. Biotechnol. 90:187-197.
25. Pikus, J. D., J. M. Studts, K. McClay, R. J. Steffan, and B. G. Fox. 1997. Changes in the regiospecificity of aromatic hydroxylation produced by active site engineering in the diiron enzyme toluene 4-monooxygenase. Biochemistry 36:9283-9289.
26. Robinson, G. K., G. M. Stephens, H. Dalton, and P. J. Geary. 1992. The production of catechols from benzene and toluene by Pseudomonas putida in glucose fed-batch culture. Biocatalysis 6:81-100.
27. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
28. Sanger, F., S. Nicklen, and A. R. Coulson. 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA 74:5463-5467.
29. Shields, M. S., S. O. Montgomery, P. J. Chapman, S. M. Cuskey, and P. H. Pritchard. 1989. Novel pathway of toluene catabolism in the trichloroethylene- degrading bacterium G4. Appl. Environ. Microbiol. 55:1624-1629.
30. Shields, M. S., M. J. Reagin, R. R. Gerger, C. Somerville, R. Schaubhut, R. Campbell, and J. Hu-Primmer. 1994. Constitutive degradation of trichloroethylene by an altered bacterium in a gas-phase bioreactor, p. 50-65. In R. E. Hinchee, A. Leeson, L. Semprini, and S. K. Ong (ed.), Bioremediation of chlorinated and polycyclic aromatic hydrocarbon compounds. Lewis Publishers, Boca Raton, Fla.
31. Smith, M. T. 1999. Benzene, NQO1, and genetic susceptibility to cancer. Proc. Natl. Acad. Sci. USA 96:7624-7626.
32. Stemmer, W. P. C. 1994. DNA shuffling by random fragmentation and reassembly: in vitro recombination for molecular evolution. Proc. Natl. Acad. Sci. USA 91:10747-10751.
33. Studts, J. M., K. H. Mitchell, J. D. Pikus, K. McClay, R. J. Steffan, and B. G. Fox. 2000. Optimized expression and purification of toluene 4-monooxygenase hydroxylase. Protein Expr. Purif. 20:58-65.
34. a.Vardar, G., and T. K. Wood. 2004. Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogollol. Appl. Environ. Microbiol. 70:3253-3262.
35. Whited, G. M., and D. T. Gibson. 1991. Separation and partial characterization of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1. J. Bacteriol. 173:3017-3020.
36. Yen, K.-M., and M. R. Karl. 1992. Identification of a new gene, tomF, in the Pseudomonas mendocina KRI gene cluster encoding toluene-4-monooxygenase. J. Bacteriol. 174:7253-7261.
37. Yen, K.-M., M. R. Karl, L. M. Blatt, M. J. Simon, R. B. Winter, P. R. Fausset, H. S. Lu, A. A. Harcourt, and K. K. Chen. 1991. Cloning and characterization of a Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase. J. Bacteriol. 173:5315-5327.