Application of nitroarene dioxygenases in the design of novel strains that degrade chloronitrobenzenes

Microbial Biotechnology

Volumn 2, Issue 2 SPEC. ISS., 2009, Pages 241-252

  Ju, Kou San ^a   Parales, Rebecca E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROTOLUENE; AROMATIC NITRO COMPOUND; CATECHOL DERIVATIVE; DIOXYGENASE; ENZYME; NITROBENZENE DERIVATIVE;

ARTICLE; BACTERIAL GROWTH; BACTERIAL METABOLISM; BACTERIAL STRAIN; COMAMONAS; CONTAMINATION; DEGRADATION; ENGINEERING; ISOMER; MUTANT; NONHUMAN; RALSTONIA; SPECIES; WILD TYPE;

BACTERIAL PROTEINS; BIODEGRADATION, ENVIRONMENTAL; COMAMONADACEAE; COMAMONAS; DIOXYGENASES; GENETIC ENGINEERING; NITROBENZENES; RALSTONIA; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

ACIDOVORAX; BACTERIA (MICROORGANISMS); COMAMONAS SP.; RALSTONIA SP.;

EID: 77952918062     PISSN: 17517907     EISSN: 17517915     Source Type: Journal    
DOI: 10.1111/j.1751-7915.2008.00083.x     Document Type: Article

References (50)

1. Bosma, T., Kruizinga, E., de Bruin, E.J., Poelarends, G.J., and Janssen, D.B. (1999) Utilization of trihalogenated propanes by Agrobacterium radiobacter AD1 through heterologous expression of the haloalkane dehalogenase from Rhodococcus sp. strain M15-3. Appl Environ Microbiol 65: 4575-4581.
2. 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.
3. Davis, R.W., Botstein, D., and Roth, J.R. (1980) Advanced Bacterial Genetics. Cold Spring Harbor, NY, USA: Cold Spring Harbor Laboratory.
4. Feltes, J., Levsen, K., Volmer, D., and Spiekermann, M. (1990) Gas chromatographic and mass spectrometric determination of nitroaromatics in water. J Chromatogr 518: 21-40.
5. Finette, B.A., Subramanian, V., and Gibson, D.T. (1984) Isolation and characterization of Pseudomonas putida PpF1 mutants defective in the toluene dioxygenase enzyme system. J Bacteriol 160: 1003-1009.
6. Friemann, R., Ivkovic-Jensen, M.M., Lessner, D.J., Yu, C.-L., Gibson, D.T., Parales, R.E., et al. (2005) Structural insights into the dioxygenation of nitroarene compounds: the crystal structure of the nitrobenzene dioxygenase. J Mol Biol 348: 1139-1151.
7. Gallegos, M.T., Molina-Henares, A.J., Zhang, X., Teran, W., Bernal, P., Alguel, Y., et al. (2007) Genomic insights in solvent tolerance and pumps that extrude toxic chemicals. In Microbial Bioremediation. Diaz, E. (ed.). Norwich, UK: Horizon Scientific Press.
8. Garner-O'Neale, L.D., Bonamy, A.F., Meek, T.L., and Patrick, B.G. (2003) Calculating group electronegativities using the Lewis-Langmuir equation. J Mol Struct 639: 151-156.
9. Gerhardt, P., Murray, R.G.E., Wood, W.A., and Krieg, N.R., eds (1994) Methods For General and Molecular Bacteriology. Washington, DC, USA: American Society for Microbiology.
10. Gibson, D.T., Koch, J.R., Schuld, C.L., and Kallio, R.E. (1968a) Oxidative degradation of aromatic hydrocarbons by microorganisms II. Metabolism of halogenated aromatic hydrocarbons. Biochemistry 7: 3795-3802.
11. Gibson, D.T., Koch, J.R., and Kallio, R.E. (1968b) Oxidative degradation of aromatic hydrocarbons by microorganisms I. Enzymatic formation of catechol from benzene. Biochemistry 7: 2653-2661.
12. Haigler, B.E., and Spain, J.C. (1991) Biotransformation of nitrobenzene by bacteria containing toluene degradative pathways. Appl Environ Microbiol 57: 3156-3162.
13. Haigler, B.E., Nishino, S.F., and Spain, J.C. (1988) Degradation of 1,2-dichlorobenzene by a Pseudomonas sp. Appl Environ Microbiol 54: 294-301.0
14. Haro, M.A., and de Lorenzo, V. (2001) Metabolic engineering of bacteria for environmental applications: construction of Pseudomonas strains for biodegradation of 2- chlorotoluene. J Biotechnol 85: 103-113.
15. Hartter, D.R. (1985) The use and importance of nitroaromatic chemicals in the chemical industry. In Toxicity of nitroaromatic compounds. Chemical Industry Institute of Toxicology Series. Rickert, D.E. (ed.). Washington, DC, USA: Hemisphere, pp. 1-14.
16. Hinteregger, C., Loidl, M., and Streichsbier, F. (1994) Pseudomonas acidovorans: a bacterium capable of mineralizing 2-chloroaniline. J Basic Microbiol 34: 77-85.
17. Huheey, J.E., Keiter, E.A., and Keiter, R.L. (1993) Inorganic Chemistry: Principles of Structure and Reactivity. 4th edn. New York, USA: HarperCollins.
18. Johnson, G.R., and Spain, J.C. (2006) Synthesis of substituted catechols using nitroarene dioxygenases. Enzyme Microb Technol 38: 142-147.
19. Johnson, G.R., Smets, B.F., and Spain, J.C. (2001) Oxidative transformation of aminodinitrotoluene isomers by multicomponent dioxygenases. Appl Environ Microbiol 67: 5460-5466.
20. Ju, K.-S., and Parales, R.E. (2006) Control of substrate specificity by active site residues in nitrobenzene 1,2- dioxygenase. Appl Environ Microbiol 72: 1817-1824.
21. Katsivela, E., Wray, V., Pieper, D.H., and Wittich, R.M. (1999) Initial reactions in the biodegradation of 1-chloro-4- nitrobenzene by a newly isolated bacterium, strain LW1. Appl Environ Microbiol 65: 1405-1412.
22. Kovach, M.E., Elzer, P.H., Hill, D.S., Robertson, G.T., Farris, M.A., Roop, R.M., and Peterson, K.M. (1995) Four new derivatives of the broad-host-range cloning vector pBBR1MCS, carrying different antibiotic-resistance cassettes. Gene 166: 175-176.
23. Kuhlmann, A., and Hegemann, W. (1997) Degradation of monochloronitrobenzenes by Pseudomonas acidovorans CA50. Acta Hydrochim Hydrobiologia 25: 298-305.
24. Lee, K.-S., Parales, J.V., Friemann, R., and Parales, R.E. (2005) Active site residues controlling substrate specificity in 2-nitrotoluene dioxygenase from Acidovorax sp. strain JS42. J Ind Microbiol Biotechnol 32: 465-473.
25. Lessner, D.J., Johnson, G.R., Parales, R.E., Spain, J.C., and Gibson, D.T. (2002) Molecular characterization and substrate specificity of nitrobenzene dioxygenase from Comamonas sp. strain JS765. Appl Environ Microbiol 68: 634-641.
26. Liu, H., Wang, S.J., and Zhou, N.Y. (2005) A new isolate of Pseudomonas stutzeri that degrades 2-chloronitrobenzene. Biotechnol Lett 27: 275-278.
27. Liu, Z.T., Wang, L.S., Chen, S.P., Li, W., and Yu, H.X. (1996) Analysis and prediction of structure-reactive toxicity relationships of substituted aromatic compounds. Bull Environ Contam Toxicol 57: 421-425.
28. Livingston, A.G. (1993) A novel membrane bioreactor for detoxifying industrial wastewater: II. Biodegradation of 3-chloronitrobenzene in an industrially produced wastewater. Biotechnol Bioeng 41: 927-936.
29. de Lorenzo, V., Cases, I., Herrero, M., and Timmis, K.N. (1993) Early and late responses of TOL promoters to pathway inducers: identification of postexponential promoters in Pseudomonas putida with lacZ-tet bicistronic reporters. J Bacteriol 175: 6902-6907.
30. Matsumoto, M., Aiso, S., Senoh, H., Yamazaki, K., Arito, H., Nagano, K., et al. (2006a) Carcinogenicity and chronic toxicity of para-chloronitrobenzene in rats and mice by twoyear feeding. J Environ Pathol Toxicol Oncol 25: 571-584.
31. Matsumoto, M., Umeda, Y., Senoh, H., Suzuki, M., Kano, H., Katagiri, T., et al. (2006b) Two-year feed study of carcinogenicity and chronic toxicity of ortho-chloronitrobenzene in rats and mice. J Toxicol Sci 31: 247-264.
32. van der Meer, J.R., Werlen, C., Nishino, S.F., and Spain, J.C. (1998) Evolution of a pathway for chlorobenzene metabolism leads to natural attenuation in contaminated groundwater. Appl Environ Microbiol 64: 4185-4193.
33. Muller, T.A., Werlen, C., Spain, J.C., and Van Der Meer, J.R. (2003) Evolution of a chlorobenzene degradative pathway among bacteria in a contaminated groundwater mediated by a genomic island in Ralstonia. Environ Microbiol 5: 163-173.
34. Munoz, R., Diaz, L.F., Bordel, S., and Villaverde, S. (2007) Inhibitory effects of catechol accumulation on benzene biodegradation in Pseudomonas putida F1 cultures. Chemosphere 68: 244-252.
35. Nishino, S.F., Spain, J.C., Lenke, H., and Knackmuss, H.-J. (1999) Mineralization of 2,4- and 2,6-dinitrotoluene in soil slurries. Environ Sci Technol 33: 1060-1064.
36. Nishino, S.F., Paoli, G.C., and Spain, J.C. (2000) Aerobic degradation of dinitrotoluenes and the pathway for bacterial degradation of 2,6-dinitrotoluene. Appl Environ Microbiol 66: 2139-2147.
37. Parales, J.V., Kumar, A., Parales, R.E., and Gibson, D.T. (1996) Cloning and sequencing of the genes encoding 2-nitrotoluene dioxygenase from Pseudomonas sp. JS42. Gene 181: 57-61.
38. Parales, J.V., Parales, R.E., Resnick, S.M., and Gibson, D.T. (1998a) Enzyme specificity of 2-nitrotoluene 2,3- dioxygenase from Pseudomonas sp. strain JS42 is determined by the C-terminal region of the a subunit of the oxygenase component. J Bacteriol 180: 1194-1199.
39. Parales, R.E., Emig, M.D., Lynch, N.A., and Gibson, D.T. (1998b) Substrate specificities of hybrid naphthalene and 2,4-dinitrotoluene dioxygenase enzyme systems. J Bacteriol 180: 2337-2344.
40. Parales, R.E., Huang, R., Yu, C.-L., Parales, J.V., Lee, F.K.N., Ivkovic-Jensen, M.M., et al. (2005) Purification, characterization, and crystallization of the components of the nitrobenzene and 2-nitrotoluene dioxygenase enzyme systems. Appl Environ Microbiol 71: 3806-3814.
41. Park, H.S., Lim, S.J., Chang, Y.K., Livingston, A.G., and Kim, H.S. (1999) Degradation of chloronitrobenzenes by a coculture of Pseudomonas putida and a Rhodococcus sp. Appl Environ Microbiol 65: 1083-1091.
42. Resnick, S.M., Torok, D.S., Lee, K., Brand, J.M., and Gibson, D.T. (1994) Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase. Appl Environ Microbiol 60: 3323-3328.
43. Sambrook, J., Fritch, E.F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, 2nd edn. Cold Spring Harbor, NY, USA: Cold Spring Harbor Laboratory.
44. Shimizu, M., Yasui, Y., and Matsumoto, N. (1983) Structural specificity of aromatic compounds with special reference to mutagenic activity in Salmonella typhimurium - a series of chloro- or fluoro-nitrobenzene derivatives. Mutat Res 116: 217-238.
45. Sikkema, J., De Bont, J.A.M., and Poolman, B. (1995) Mechanisms of membrane toxicity of hydrocarbons. Microbiol Rev 59: 201-222.
46. Smibert, R.M., and Krieg, N.R. (1981) General characterization. In Manual of Methods for General Bacteriology. Gerhardt, P., Murray, R.G.E., Costilow, R.N., Nester, E.W., Wood, W.A., Krieg, N.R., and Phillips, G.B. (eds). Washington, DC, USA: American Society for Microbiology, pp. 409-443.
47. Stanier, R.Y., Palleroni, N.J., and Doudoroff, M. (1966) The aerobic pseudomonads: a taxonomic study. J Gen Microbiol 43: 159-271.
48. Suen, W.-C., Haigler, B.E., and Spain, J.C. (1996) 2,4- Dinitrotoluene dioxygenase from Burkholderia sp. strain DNT: similarity to naphthalene dioxygenase. J Bacteriol 178: 4926-4934.
49. Wu, J.F., Jiang, C.Y., Wang, B.J., Ma, Y.F., Liu, Z.P., and Liu, S.J. (2006) Novel partial reductive pathway for 4-chloronitrobenzene and nitrobenzene degradation in Comamonas sp. strain CNB-1. Appl Environ Microbiol 72: 1759-1765.
50. Zhen, D., Liu, H.,Wang, S.J., Zhang, J.J., Zhao, F., and Zhou, N.Y. (2006) Plasmid-mediated degradation of 4-chloronitrobenzene by newly isolated Pseudomonas putida strain ZWL73. Appl Microbiol Biotechnol 72: 797-803.