Biochemical characterization of the tetrachlorobenzoquinone reductase involved in the biodegradation of pentachlorophenol

International Journal of Molecular Sciences

Volumn 9, Issue 3, 2008, Pages 198-212

  Chen, Lifeng ^a   Yang, Jian ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Biodegradation; Enzyme; Homology modeling; Yin Yang regulation

Indexed keywords

BENZOQUINONE DERIVATIVE; FLAVINE MONONUCLEOTIDE; PENTACHLOROPHENOL; TETRACHLOROBENZOQUINONE REDUCTASE; TETRACHLOROHYDROQUINONE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM; BINDING SITE; BIODEGRADATION; CATALYSIS; CONCENTRATION RESPONSE; CYTOTOXICITY; DOWNSTREAM PROCESSING; ENZYME ACTIVITY; ENZYME BINDING; IN VIVO STUDY; MOLECULAR CLONING; NONHUMAN; PH; PROTEIN EXPRESSION; PURIFICATION; SPHINGOBIUM CHLOROPHENOLICUM; STATISTICAL SIGNIFICANCE;

SPHINGOBIUM CHLOROPHENOLICUM;

EID: 41649083350     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms9030198     Document Type: Article

References (37)

1. Frank, R.; Braun, H.E.; Ripley, B.D.; Clegg, B.S. Contamination of rural ponds with pesticides, 1971-85, Ontario, Canada. Bull. Environ. Contam. Toxicol. 1990, 44, 401-409.
2. McAllister, K.A.; Lee, H.; Trevors, J.T. Microbial degradation of pentachlorophenol. Biodegradation 1996, 7, 1-40.
3. Ingram, L.L.; Tarlton, K. Effect of physical properties of pentachlorophenol and creosote components on vaporization from treated wood: Review of prior data. Forest Prod. J. 2005, 55, 86-89.
4. Thompson, T.S.; Treble, R.G.; Mariasegaram, M. Determination of atmospheric contamination by pentachlorophenol using pine needles located near treated utility pole storage sites. Bull. Environ. Contam. Toxicol. 1997, 59, 548-555.
5. Sai, K.; Kang, K.S.; Hirose, A.; Hasegawa, R.; Trosko, J.E.; Inoue, T. Inhibition of apoptosis by pentachlorophenol in v-myc-transfected rat liver epithelial cells: relation to down-regulation of gap junctional intercellular communication. Cancer Lett. 2001, 173, 163-174.
6. Khurana, V.; Barkin, J.S. Pancreatitis induced by environmental toxins. Pancreas 2001, 22, 102-105.
7. Daniel, V.; Huber, W.; Bauer, K.; Suesal, C.; Mytilineos, J.; Melk, A.; Conradt, C.; Opelz, G. Association of elevated blood levels of pentachlorophenol (PCP) with cellular and humoral immunodeficiencies. Arch. Environ. Health 2001, 56, 77-83.
8. Peper, M.; Ertl, M.; Gerhard, I. Long-term exposure to wood-preserving chemicals containing pentachlorophenol and lindane is related to neurobehavioral performance in women. Am. J. Ind. Med. 1999, 35, 632-641.
9. D'Angelo, E.M.; Reddy, K.R. Aerobic and anaerobic transformations of pentachlorophenol in wetland soils. Soil Sci. Soc. Am. J. 2000, 64, 933-943.
10. Seidler, J.R.; Landau, M.; Dierberg, F.E.; Pierce, R.H. Persistence of pentachlorophenol in a wastewater-estuarine aquaculture system. Bull. Environ. Contam. Toxicol. 1986, 36, 101-108.
11. Tisch, M.; Faulde, M.K.; Maier, H. Genotoxic effects of pentachlorophenol, lindane, transfluthrin, cyfluthrin, and natural pyrethrum on human mucosal cells of the inferior and middle nasal conchae. Am. J. Rhinol. 2005, 19, 141-151.
12. Villela, I.V.; de Oliveira, I.M.; da Silva, J.; Henriques, J.A. DNA damage and repair in haemolymph cells of golden mussel (Limnoperna fortunei) exposed to environmental contaminants. Mutat. Res. 2006, 605, 78-86.
13. Xun, L.; Topp, E.; Orser, C.S. Diverse substrate range of a Flavobacterium pentachlorophenol hydroxylase and reaction stoichiometries. J. Bacteriol. 1992, 174, 2898-2902.
14. Xun, L.; Orser, C.S. Purification and properties of pentachlorophenol hydroxylase, a flavoprotein from Flavobacterium sp. strain ATCC 39723. J. Bacteriol. 1991, 173, 4447-4453.
15. Xun, L.; Topp, E.; Orser, C.S. Purification and characterization of a tetrachloro-p-hydroquinone reductive dehalogenase from a Flavobacterium sp. J. Bacteriol. 1992, 174, 8003-8007.
16. Miyauchi, K.; Adachi, Y.; Nagata, Y.; Takagi, M. Cloning and sequencing of a novel meta-cleavage dioxygenase gene whose product is involved in degradation of γ-hexachlorocyclohexane in Sphingomonas paucimobilis. J. Bacteriol. 1999, 181, 6712-6719.
17. McCarthy, D.L.; Claude, A.A.; Copley, S.D. In vivo levels of chlorinated hydroquinones in a pentachlorophenol-degrading bacterium. Appl. Environ. Microbiol. 1997, 63, 1883-1888.
18. Copley, S.D. Evolution of a metabolic pathway for degradation of a toxic xenobiotic: the patchwork approach. Trends Biochem. Sci. 2000, 25, 261-265.
19. Dai, M.; Rogers, J.B.; Warner, J.R.; Copley, S.D. A previously unrecognized step in pentachlorophenol degradation in Sphingobium chlorophenolicum is catalyzed by tetrachlorobenzoquinone reductase (PcpD). J. Bacteriol. 2003, 185, 302-310.
20. Cai, M.; Xun, L. Organization and regulation of pentachlorophenol- degrading genes in Sphingobium chlorophenolicum ATCC 39723. J. Bacteriol. 2002, 184, 4672:4680.
21. Maupin-Furlow, J.; Ferry, J.G. Characterization of the cdhD and cdhE genes encoding subunits of the corrinoid/iron-sulfur enzyme of the CO dehydrogenase complex from Methanosarcina thermophila. J. Bacteriol. 1996, 178, 340-346.
22. Ventura, S.; Villaverde, A. Protein quality in bacterial inclusion bodies. Trends Biotechnol. 2006, 24, 179-185.
23. Crawford, R.L. Biodegradation of pentachlorophenol. In U.S. Patent No. 4713340, 1987.
24. Hatakeyama, K.; Harada, T.; Suzuki, S.; Watanabe, Y.; Kagamiyama, H. Purification and characterization of rat liver GTP cyclohydrolase I. Cooperative binding of GTP to the enzyme. J. Biol. Chem. 1989, 264, 21660-21664.
25. Kiefer, Jr. P.M.; Copley, S.D. Characterization of the initial steps in the reductive dehalogenation catalyzed by tetrachlorohydroquinone dehalogenase. Biochemistry 2002, 41, 1315-1322.
26. Kiefer, Jr. P.M.; McCarthy, D.L.; Copley, S.D. The reaction catalyzed by tetrachlorohydroquinone dehalogenase does not involve nucleophilic aromatic substitution. Biochemistry 2002, 41, 1308-1314.
27. Warner, J.R.; Lawson, S.L.; Copley, S.D. A mechanistic investigation of the thiol-disulfide exchange step in the reductive dehalogenation catalyzed by tetrachlorohydroquinone dehalogenase. Biochemistry 2005, 44, 10360-10368.
28. Xun, L.; Topp, E.; Orser, C.S. Confirmation of oxidative dehalogenation of pentachlorophenol by a Flavobacterium pentachlorophenol hydroxylase. J. Bacteriol. 1992, 174, 5745-5747.
29. Topp, E.; Xun, L.; Orser, C.S. Biodegradation of the herbicide bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) by purified pentachlorophenol hydroxylase and whole cells of Flavobacterium sp. strain ATCC 39723 is accompanied by cyanogenesis. Appl. Environ. Microbiol. 1992, 58, 502-506.
30. Correll, C.C.; Batie, C.J.; Ballou, D.P.; Ludwig, M.L. Phthalate dioxygenase reductase: a modular structure for electron transfer from pyridine nucleotides to [2Fe-2S]. Science 1992, 258, 1604-1610.
31. Morris, G.M.; Goodsell, D.S.; Halliday, R.S.; Huey, R.; Hart, W.E.; Belew, R.K.; Olson, A.J. Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J. Computational Chemistry 1998, 19, 1639-1662.
32. Böhm, G.; Muhr, R.; Jaenicke, R. Quantitative analysis of protein far UV circular dichroism spectra by neural networks. Protein Eng. 1992, 5, 191-195.
33. Thompson, J.D.; Higgins, D.G.; Gibson, T.J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994, 22, 4673-4680.
34. Marti-Renom, M.A.; Stuart, A.; Fiser, A.; Sánchez, R.; Melo, F.; Sali, A. Comparative protein structure modeling of genes and genomes. Annu. Rev. Biophys. Biomol. Struct. 2000, 29, 291-325.
35. Laskowski, R.A.; McArthur, M.W.; Moss, D.S.; Thornton, J.M. PROCHECK: A program to check the stereochemical quality of protein structures. J. Appl. Cryst. 1993, 26, 283-291.
36. Sippl, M.J. Recognition of errors in three-dimensional structures of proteins. Proteins 1993, 17, 355-362.
37. Luthy, R.; Bowie, J.U.; Eisenberg, D. Assessment of protein models with three-dimensional profiles. Nature 1992, 356, 83-85.