Microbial Degradation of Polychlorophenols

  • Luying Xun
Part of the Environmental Science and Engineering book series (ESE)


Polychlorophenols are major environmental pollutants, and their degradation by microorganisms has been extensively studied for the purpose of bioremediation. Three different metabolic pathways for aerobic degradation of polychlorophenols have been completely worked out, revealing the metabolic diversity for these structurally similar compounds. Substituted quinols, rather than catechols, are key metabolic intermediates of polychlorophenol biodegradation. Substituted quinols and quinones are also called as p–hydroquinones and p-benzoquinones, reflecting the reduced and oxidized forms. For example, tetrachloroquinol is the same as tetrachloro-p-hydroquinone, and tetrachloroquinone is often referred as tetrachloro-p-benzoquinone. Characterization of individual enzymes has led to the discoveries of novel dechlorination mechanisms. The genes coding for the enzymes have been cloned and sequenced, and the gene organization and regulation suggest that recent gene recruitments have occurred for the degradation of some polychlorophenols.


Flavin Adenine Dinucleotide Metabolic Intermediate Glutathione Transferase Reductive Dechlorination Quinone Reductase 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



I began working on polychlorophenol degradation as a postdoctoral scientist with Dr. Cindy S. Orser at University of Idaho and have continued the research as a faculty member at Washington State University. Pacific Northwest National Laboratory provided me with lab space and equipment from 1992 to 1997. National Science Foundation has supported the research with grants MCB-921873, MCB-9722970, MCB-0323167 and MCB-1021148. My graduate students, postdoctoral scientists, and coworkers have significantly contributed to the progress summarized here. We have collaborated with Dr. A. M. Chakrabarty’s group at University of Illinois at Chicago on 2,4,5-T degradation.


  1. Anandarajah K, Kiefer PMJ, Donohoe BS, Copley SD (2000) Recruitment of a double bond isomerase to serve as a reductive dehalogenase during biodegradation of pentachlorophenol. Biochemistry 39:5303–5311Google Scholar
  2. Apajalahti JH, Salkinoja-Salonen MS (1987) Complete dechlorination of tetrachlorohydroquinone by cell extracts of pentachlorophenol-induced Rhodococcus chlorophenolicus. J Bacteriol 169:5125–5130Google Scholar
  3. Aranda C, Godoy F, Gonzalez G, Homo J, Martinez M (1999) Effects of glucose and phenylalanine upon 2,4,6-trichlorophenol degradation by Pseudomonas paucimobilis S37 cells in a no-growth state. Microbios 100:73–82Google Scholar
  4. Bateman A, Birney E, Cerruti L, Durbin R, Etwiller L, Eddy SR (2002) The Pfam protein families database. Nucleic Acids Res 30:276–280Google Scholar
  5. Belchik SM, Xun L (2008) Functions of flavin reductase and quinone reductase in 2,4,6-trichlorophenol degradation by Cupriavidus necator JMP134. J Bacteriol 190:1615–1619Google Scholar
  6. Belchik SM, Schaeffer SM, Hasenoehrl S, Xun L (2010) A beta-barrel outer membrane protein facilitates cellular uptake of polychlorophenols in Cupriavidus necator. Biodegradation 21:431–439Google Scholar
  7. Birchmore RJ, Meneley JC (1979) Prochloraz-a new foliar fungicide with potential in a wide range of crops. Phytopathology 69:1022–1026Google Scholar
  8. Bisaillon A, Beaudet R, Lépine F, Déziel E, Villemur R (2010) Identification and characterization of a novel CprA reductive dehalogenase specific to highly chlorinated phenols from Desulfitobacterium hafniense strain PCP-1. Appl Environ Microbiol 76(22):7536–7540. doi: 10.1128/AEM.01362-10 Google Scholar
  9. Bock C, Kroppenstedt RM, Schmidt U, Diekmann H (1996) Degradation of prochloraz and 2,4,6-trichlorophenol by environmental bacterial strains. Appl Microbiol Biotech 45:257–262Google Scholar
  10. Bouchard B, Beaudet R, Villemur R, McSween G, Lepine G, Bisaillon JG (1996) Isolation and characterization of Desulfitobacterium frappieri sp. nov., an anaerobic bacterium which reductively dechlorinates pentachlorophenol to 3-chlorophenol. Int J Syst Bacteriol 46:1010–1015Google Scholar
  11. Boyer A, Page-BeLanger R, Saucier M, Villemur R, Lépine F, Juteau P, Beaudet R (2003) Purification, cloning and sequencing of an enzyme mediating the reductive dechlorination of 2,4,6-trichlorophenol from Desulfitobacterium frappieri PCP-1. Biochem J 373:297–303Google Scholar
  12. Briglia M, Eggen RI, Van Elsas DJ, De Vos WM (1994) Phylogenetic evidence for transfer of pentachlorophenol-mineralizing Rhodococcus chlorophenolicus PCP-I(T) to the genus Mycobacterium. Int J Syst Bacteriol 44:494–498Google Scholar
  13. Briglia M, Rainey FA, Stackebrandt E, Schraa G, Salkinoja-Salonen MS (1996) Rhodococcus percolatus sp. nov., a bacterium degrading 2,4,6-trichlorophenol. Int J Syst Bacteriol 46:23–30Google Scholar
  14. Cai M, Xun L (2002) Organization and regulation of pentachlorophenol-degrading genes in Sphingobium chlorophenolicum ATCC 39723. J Bacteriol 184:4672–4680Google Scholar
  15. Chanama S, Crawford RL (1997) Mutational analysis of pcpA and its role in pentachlorophenol degradation by Sphingomonas (Flavobacterium) chlorophenolica ATCC 39723. Appl Environ Microbiol 63:4833–4838Google Scholar
  16. Chu JP, Kirsch EJ (1972) Metabolism of pentachlorophenol by an axenic bacterial culture. Appl Microbiol 23:1033–1035Google Scholar
  17. Clement P, Matus V, Cardenas L, Gonzalez B (1995) Degradation of trichlorophenols by Alcaligenes eutrophus JMP134. FEMS Microbiol Lett 127:51–55Google Scholar
  18. Cline RE, Hill RHJ, Phillips DL, Needham LL (1989) Pentachlorophenol measurements in body fluids of people in log homes and workplaces. Arch Environ Contam Toxicol 18:475–481Google Scholar
  19. Coque JJ, Alvarez-Rodriguez ML, Larriba G (2003) Characterization of an inducible chlorophenol O-methyltransferase from Trichoderma longibrachiatum involved in the formation of chloroanisoles and determination of its role in cork taint of wines. Appl Environ Microbiol 69:5089–5095Google Scholar
  20. Crawford RL, Ederer MM (1999) Phylogeny of Sphingomonas species that degrade pentachlorophenol. J Ind Microbiol Biotechnol 23:320–325Google Scholar
  21. Crawford RL, Mohn WW (1985) Microbial removal of pentachlorophenol from soil using a Flavobacterium. Enzyme Microb Technol 7:617–620Google Scholar
  22. Crosby DG (1981) Environmental chemistry of pentachlorophenol. Pure Appl Chem 53:1052–1080Google Scholar
  23. Cunarro J, Weiner MW (1975) Mechanism of action of agents which uncouple oxidative phosphorylation: direct correlation between proton-carrying and respiratory-releasing properties using rat liver mitochondria. Biochim Biophys Acta 387:234–240Google Scholar
  24. Dahlhaus M, Almstadt E, Henschke P, Luttgert S, Appel KE (1995) Induction of 8-hydroxy-2-deoxyguanosine and single-strand breaks in DNA of V79 cells by tetrachloro-p-hydroquinone. Mutat Res 329:29–36Google Scholar
  25. Dai M, Rogers JB, Warner JR, Copley SD (2003) A previously unrecognized step in pentachlorophenol degradation in Sphingobium chlorophenolicum is catalyzed by tetrachlorobenzoquinone reductase (PcpD). J Bacteriol 185:302–310Google Scholar
  26. Delaney SM, Mavrodi DV, Bonsall RF, Thomashow LS (2001) phzO, a gene for biosynthesis of 2-hydroxylated phenazine compounds in Pseudomonas aureofaciens 30–84. J Bacteriol 183:318–327Google Scholar
  27. Dixon DP, Davis BG, Edwards R (2002) Functional divergence in the glutathione transferase superfamily in plants. Identification of two classes with putative functions in redox homeostasis in Arabidopsis thaliana. J Biol Chem 277:30859–30869Google Scholar
  28. Duncan CG, Deverall FJ (1964) Degradation of wood preservatives by fungi. Appl Microbiol 12:57–62Google Scholar
  29. Ederer MM, Crawford RL, Herwig RP, Orser CS (1997) PCP degradation is mediated by closely related strains of the genus Sphingomonas. Mol Ecol 6:39–49Google Scholar
  30. Entsch B, Ballou DP, Massey V (1976) Flavin-oxygen derivatives involved in hydroxylation by p-hydroxybenzoate hydroxylase. J Biol Chem 251:2550–2563Google Scholar
  31. EPA (2006) Toxic Release Inventory: Public Data Release.
  32. Escher BI, Snozzi M, Schwarzenbach P (1996) Uptake, speciation, and uncoupling activity of substituted phenols in energy transducing membranes. Environ Sci Technol 30:3071–3079Google Scholar
  33. Firestone D (1978) The 2,3,7,8-trtrachlorodibenzo-para-dioxin problem: a review. Stockholm Ecol Bulletin 27:39–52Google Scholar
  34. Galán B, Díaz E, Prieto MA, García JL (2000) Functional analysis of the small component of the 4-hydroxyphenylacetate 3-monnooxygenase of Escherichia coli W: a prototype of a new Flavin: NAD(P)H reductase subfamily. J Bacteriol 182:627–636Google Scholar
  35. Garcera A, Barreto L, Piedrafita L, Tamarit J, Herrero E (2006) Saccharomyces cerevisiae cells have three Omega class glutathione S-transferases acting as 1-Cys thiol transferases. Biochem J 398:187–196Google Scholar
  36. Gisi MR, Xun L (2003) Characterization of chlorophenol 4-monooxygenase (TftD) and NADH:flavin adenine dinucleotide oxidoreductase (TftC) of Burkholderia cepacia AC1100. J Bacteriol 185:2786–2792Google Scholar
  37. Golovleva LA, Pertsova RN, Evtushenko LI, Baskunov BP (1990) Degradation of 2,4,5-trichlorophenoxyacetic acid by a Nocardioides simplex culture. Biodegradation 1:263–271Google Scholar
  38. Golovleva LA, Zaborina O, Pertsova R, Baskunov B, Schurukhin Y, Kuzmin S (1992) Degradation of polychlorinated phenols by Streptomyces rochei 303. Biodegradation 2:201–208Google Scholar
  39. Habash M, Chu BC, Trevors JT, Lee H (2009) Mutational study of the role of N-terminal amino acid residues in tetrachlorohydroquinone reductive dehalogenase from Sphingomonas sp. UG30. Res Microbiol 60:553–559Google Scholar
  40. Haggblom MM, Nohynek LJ, Palleroni NJ, Kronqvist K, Nurmiaho-Lassila EL, Salkinoja-Salonen MS (1994) Transfer of polychlorophenol-degrading Rhodococcus chlorophenolicus to the genus Mycobacterium as Mycobacterium chlorophenolicum comb nov. Int J Syst Bacteriol 44:485–493Google Scholar
  41. Haigler BE, Suen WC, Spain JC (1996) Purification and sequence analysis of 4-methyl-5-nitrocatechol oxygenase from Burkholderia sp strain DNT. J Bacteriol 178:6019–6024Google Scholar
  42. Harwood CS, Parales RE (1996) The ß-ketoadipate pathway and the biology of self-identity. Annu Rev Microbiol 50:553–590Google Scholar
  43. Haugland RA, Sangodkar UM, Sferra PR, Chakrabarty AM (1991) Cloning and characterization of a chromosomal DNA region required for growth on 2,4,5-T by Pseudomonas cepacia AC1100. Gene 100:65–73Google Scholar
  44. Hoekstra E, de Weerd H, de Leer E, Brinkman U (1999) Natural formation of chlorinated phenols, dibenzo-p-dioxins, and dibenzofurans in soil of a douglas fir forest. Environ Sci Technol 33:2543–2549Google Scholar
  45. Huang Y, Xun R, Chen G, Xun L (2008) The maintenance role of a glutathionyl-hydroquinone lyase (PcpF) in pentachlorophenol degradation by Sphingobium chlorophenolicum ATCC 39723. J Bacteriol 190:7595–7600Google Scholar
  46. Hubner A, Hendrickson W (1997) A fusion promoter created by a new insertion sequence, IS1490, activates transcription of 2,4,5-trichlorophenoxyacetic acid catabolic genes in Burkholderia cepacia AC1100. J Bacteriol 179:2717–2723Google Scholar
  47. Hubner A, Danganan CE, Xun L, Chakrabarty AM, Hendrickson W (1998) Genes for 2,4,5-trichlorophenoxyacetic acid metabolism in Burkholderia cepacia AC1100: characterization of the tftC and tftD genes and locations of the tft operons on multiple replicons. Appl Environ Microbiol 64:2086–2093Google Scholar
  48. Husain M, Entsch B, Ballou DP, Massey V, Chapman PJ (1980) Fluoride elimination from substrates in hydroxylation reaction catalyzed by p-hydroxybenzoate hydroxylase. J Biol Chem 255:4189–4197Google Scholar
  49. Ide A, Niki Y, Sakamoto F, Watanabe I, Wantanabe H (1972) Decomposition of pentachlorophenol in paddy soil. Agric Biol Chem 36:1937–1944Google Scholar
  50. Imai R, Nagata Y, Fukuda M, Takagi M, Yano K (1991) Molecular cloning of a Pseudomonas paucimobilis gene encoding a 17-kilodalton polypeptide that eliminates HCl molecules from gamma-hexachlorocyclohexane. J Bacteriol 173:6811–6819Google Scholar
  51. Inouye S (1994) NAD(P)H-flavin oxidoreductase from the bioluminescent bacterium, Vibrio fischeri ATCCis a flavoprotein. FEBS Lett 347:163–168Google Scholar
  52. Kaiser J (2000) Just how bad is dioxin? Science 288:1941–1944Google Scholar
  53. Karns JS, Duttagupta S, Chakrabarty AM (1983) Regulation of 2,4,5-trichlorophenoxyacetic acid and chlorophenol metabolism in Pseudomonas cepacia AC1100. Appl Environ Microbiol 46:1182–1186Google Scholar
  54. Kaschabek SR, Kuhn B, Muller D, Schmidt E, Reineke W (2002) Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: purification and characterization of 3-oxoadipate:succinyl-coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase. J Bacteriol 184:207–215Google Scholar
  55. Kellogg ST, Chatterjee DK, Chakrabarty AM (1981) Plasmid-assisted molecular breeding: new technique for enhanced biodegradation of persistent toxic chemicals. Science 214:1133–1135Google Scholar
  56. Kilbane JJ, Chatterjee DK, Karns JS, Kellogg ST, Chakrabarty AM (1982) Biodegradation of 2,4,5-trichlorophenoxyacetic acid by a pure culture of Pseudomonas cepacia. Appl Environ Microbiol 44:72–78Google Scholar
  57. Kirchner U, Westphal AH, Muller R, van Berkel WJ (2003) Phenol hydroxylase from Bacillus thermoglucosidasius A7, a two-protein component monooxygenase with a dual role for FAD. J Biol Chem 278:47545–47553Google Scholar
  58. Kiyohara H, Hatta T, Ogawa Y, Kakuda T, Yokoyama H, Takizawa N (1992) Isolation of Pseudomonas pickettii strains that degrade 2,4,6-trichlorophenol and their dechlorination of chlorophenols. Appl Environ Microbiol 58:1276–1283Google Scholar
  59. Lamar RT, Dietrich DM (1990) In situ depletion of pentachlorophenol from contaminated soil by Phanerochaete spp. Appl Environ Microbiol 56:3093–3100Google Scholar
  60. Lamar RT, Dietrich DM (1992) Use of lignin-degrading fungi in the disposal of pentachlorophenol-treated wood. J Ind Microbiol 9:181–191Google Scholar
  61. Lamar RT, Evans JW (1993) Solid-phase treatment of a pentachlorophenol-contaminated soil using lignin-degradting fungi. Environ Sci Technol 27:2566–2571Google Scholar
  62. Lange CC, Schneider BJ, Orser CS (1996) Verification of the role of PCP 4-monooxygenase in chlorine elimination from pentachlorophenol by Flavobacterium sp. strain ATCC 39723. Biochem Biophys Res Commun 219:146–149Google Scholar
  63. Lei B, Liu M, Huang S, Tu SC (1994) Vibrio harveyi NADPH-flavin oxidoreductase: cloning, sequencing and overexpression of the gene and purification and characterization of the cloned enzyme. J Bacteriol 176:3552–3558Google Scholar
  64. Li DY, Eberspacher J, Wagner B, Kuntzer J, Lingens F (1991) Degradation of 2,4,6-trichlorophenol by Azotobacter sp. strain GP1. Appl Environ Microbiol 57:1920–1928Google Scholar
  65. Louie TM, Webster CM, Xun L (2002) Genetic and biochemical characterization of a novel 2,4,6-trichlorophenol degradation pathway in Ralstonia eutropha JMP134. J Bacteriol 184:3492–3500Google Scholar
  66. Lü Z, Min H, Wu S, Ruan A (2003) Phylogenetic and degradation characterization of Burkholderia cepacia WZ1 degrading herbicide quinclorac. J Environ Sci Health B 38:771–782Google Scholar
  67. Lyr H (1963) Enzymatische detoxifikation chlorierter phenole. Phytopath Zeitschr 47:73–83Google Scholar
  68. Mannisto MK, Tiirola MA, Salkinoja-Salonen MS, Kulomaa MS, Puhakka JA (1999) Diversity of chlorophenol-degrading bacteria isolated from contaminated boreal groundwater. Arch Microbiol 171:189–197Google Scholar
  69. Marco A, Cuesta A, Pedrola L, Palau F, Marín I (2004) Evolutionary and structural analyses of GDAP1, involved in Charcot-Marie-Tooth disease, characterize a novel class of glutathione transferase-related genes. Mol Biol Evol 21:176–187Google Scholar
  70. Matus V, Sanchez MA, Martinez M, Gonzalez B (2003) Efficient degradation of 2,4,6-Trichlorophenol requires a set of catabolic genes related to tcp genes from Ralstonia eutropha JMP134(pJP4). Appl Environ Microbiol 69:7108–7115Google Scholar
  71. Merz V, Weith W (1872) On the characteristics of pentachlorophenol (in German). Ber Dtsch Chem Ges 5:458–463Google Scholar
  72. Middaugh DP, Thomas RL, Lantz SE, Heard CS, Mueller JG (1994) Field-scale testing of a hyperfiltration unit for removal of creosote and pentachlorophenol from ground water: chemical and biological assessment. Arch Environ Contam Toxicol 26:309–319Google Scholar
  73. Miethling R, Karlson U (1996) Accelerated mineralization of pentachlorophenol in soil upon inoculation with Mycobacterium chlorophenolicum PCP1 and Sphingomonas chlorophenolica RA2. Appl Environ Microbiol 62:4361–4366Google Scholar
  74. Mikesell MD, Boyd SA (1986) Complete reductive dechlorination and mineralization of pentachlorophenol by anaerobic microorganisms. Appl Environ Microbiol 52:861–865Google Scholar
  75. Nohynek LJ, Nurmiaho-Lassila EL, Suhonen EL, Busse HJ, Mohammadi M, Hantula J (1996) Description of chlorophenol-degrading Pseudomonas sp. strains KF1T, KF3, and NKF1 as a new species of the genus Sphingomonas, Sphingomonas subarctica sp. nov. Int J Syst Bacteriol 46:1042–1055Google Scholar
  76. Ohtsubo Y, Miyauchi K, Kanda K, Hatta T, Kiyohara H, Senda T (1999) PcpA, which is involved in the degradation of pentachlorophenol in Sphingomonas chlorophenolica ATCC39723, is a novel type of ring-cleavage dioxygenase. FEBS Lett 459:395–598Google Scholar
  77. Orser CS, Lange CC (1994) Molecular analysis of pentachlorophenol degradation. Biodegradation 5:277–288Google Scholar
  78. Orser CS, Dutton J, Lange C, Jablonski P, Xun L, Hargis M (1993a) Characterization of a Flavobacterium glutathione S-transferase gene involved in reductive dechlorination. J Bacteriol 175:2640–2644Google Scholar
  79. Orser CS, Lange CC, Xun L, Zahrt TC, Schneider BJ (1993b) Cloning, sequence analysis, and expression of the Flavobacterium pentachlorophenol-4-monooxygenase gene in Escherichia coli. J Bacteriol 175:411–416Google Scholar
  80. Padilla L, Matus V, Zenteno P, Gonzalez B (2000) Degradation of 2,4,6-trichlorophenol via chlorohydroxyquinol in Ralstonia eutropha JMP134 and JMP222. J Basic Microbiol 40:243–249Google Scholar
  81. Proudfoot AT (2003) Pentachlorophenol poisoning. Toxicol Rev 22:3–11Google Scholar
  82. Puhakka JA, Herwig RP, Koro PM, Wolfe GV, Ferguson JF (1995) Biodegradation of chlorophenols by mixed and pure cultures from a fluidized-bed reactor. Appl Microbiol Biotechnol 42:951–957Google Scholar
  83. Raymond KN, Dertz EA, Kim SS (2003) Enterobactin: an archetype for microbial iron transport. Proc Natl Acad Sci USA 100:3584–3588Google Scholar
  84. Reddy GV, Gold MH (2000) Degradation of pentachlorophenol by Phanerochaete chrysosporium: intermediates and reactions involved. Microbiology 146:405–413Google Scholar
  85. Reddy GV, Gold MH (2001) Purification and characterization of glutathione conjugate reductase: a component of the tetrachlorohydroquinone reductive dehalogenase system from Phanerochaete chrysosporium. Arch Biochem Biophys 391:271–277Google Scholar
  86. Reddy GV, Gelpke MD, Gold MH (1998) Degradation of 2,4,6-trichlorophenol by Phanerochaete chrysosporium: involvement of reductive dechlorination. J Bacteriol 180:5159–5164Google Scholar
  87. Rice JF, Menn FM, Hay AG, Sanseverino J, Sayler GS (2005) Natural selection for 2,4,5-trichlorophenoxyacetic acid mineralizing bacteria in agent orange contaminated soil. Biodegradation 16:501–512Google Scholar
  88. Saber DL, Crawford RL (1985) Isolation and characterization of Flavobacterium strains that degrade pentachlorophenol. Appl Environ Microbiol 50:1512–1518Google Scholar
  89. Sánchez MA, González B (2007) Genetic characterization of 2, 4, 6-trichlorophenol degradation in Cupriavidus necator JMP134. Appl Environ Microbiol 73:2769–2776Google Scholar
  90. Sangodkar UM, Chapman PJ, Chakrabarty AM (1988) Cloning, physical mapping and expression of chromosomal genes specifying degradation of the herbicide 2,4,5-T by Pseudomonas cepacia AC1100. Gene 71:267–277Google Scholar
  91. Sharma A, Thakur IS, Dureja P (2009) Enrichment, isolation and characterization of pentachlorophenol degrading bacterium Acinetobacter sp. ISTPCP-3 from effluent discharge site. Biodegradation 5:643–650Google Scholar
  92. Steiert JG, Crawford RL (1986) Catabolism of pentachlorophenol by a Flavobacterium sp. Biochem Biophys Res Commun 141:825–830Google Scholar
  93. Steiert JG, Pignatello JJ, Crawford RL (1987) Degradation of chlorinated phenols by a pentachlorophenol-degrading bacterium. Appl Environ Microbiol 53:907–910Google Scholar
  94. Stintzi A, Cornelis P, Hohnadel D, Meyer JM, Dean C, Poole K (1996) Novel pyoverdine biosynthesis gene(s) of Pseudomonas aeruginosa PAO. Microbiology 142:1181–1190Google Scholar
  95. Suckling J, Mansson P-H, Mann J, Morgan J (1999) Corky wines linked to cellars in France. In: Wine Spectator. In February 28, 1999 IssueGoogle Scholar
  96. Takeuchi M, Hamana K, Hiraishi A (2001) Proposal of the genus Sphingomonas sensu stricto and three new genera, Sphingobium, Novosphingobium and Sphingopyxis, on the basis of phylogenetic and chemotaxonomic analyses. Int J Syst Evol Microbiol 51:1405–1417Google Scholar
  97. Takizawa N, Yokoyama H, Yanagihara K, Hatta T, Kiyohara H (1995) A locus of Pseudomonas pickettii DTP0602, had, that encodes 2,4,6-trichlorophenol-4-dechlorinase with hydroxylase activity, and hydroxylation of various chlorophenols by the enzyme. J Ferment Bioeng 80:318–326Google Scholar
  98. Tiirola MA, Wang H, Paulin L, Kulomaa MS (2002) Evidence for natural horizontal transfer of the pcpB gene in the evolution of polychlorophenol-degrading sphingomonads. Appl Environ Microbiol 68:4495–4501Google Scholar
  99. Tiirola MA, Busse HJ, Kämpfer P, Männistö MK (2005) Novosphingobium lentum sp nov., a psychrotolerant bacterium from a polychlorophenol bioremediation process. Int J Syst Evol Microbiol 55:583–588Google Scholar
  100. Trantirek L, Hynkova K, Nagata Y, Murzin A, Ansorgová A, Sklenár V, Damborský J (2001) Reaction mechanism and stereochemistry of gamma-hexachlorocyclohexane dehydrochlorinase LinA. J Biol Chem 276:7734–7740Google Scholar
  101. Uhl S, Schmid P, Schlatter C (1986) Pharmacokinetics of pentachlorophenol in man. Arch Toxicol 58:182–186Google Scholar
  102. Uotila JS, Kitunen VH, Coote T, Saastamoinen T, Salkinoja-Salonen MS, Apajalahti JH (1995) Metabolism of halohydroquinones in Rhodococcus chlorophenolicus PCP-1. Biodegradation 6:119–126Google Scholar
  103. Wackett LP, Kwart LD, Gibson DT (1988) Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry 27:1360–1367Google Scholar
  104. Wang CC, Lee CM, Lu CJ, Chuang MS, Huang CZ (2000) Biodegradation of 2,4,6-trichlorophenol in the presence of primary substrate by immobilized pure culture bacteria. Chemosphere 41:1873–1879Google Scholar
  105. Wang YJ, Lee CC, Chang WC, Liou HB, Ho YS (2001) Oxidative stress and liver toxicity in rats and human hepatoma cell line induced by pentachlorophenol and its major metabolite tetrachlorohydroquinone. Toxicol Lett 122:157–169Google Scholar
  106. Warner JR, Lawson SL, Copley SD (2005) A mechanistic investigation of the thiol-disulfide exchange step in the reductive dehalogenation catalyzed by tetrachlorohydroquinone dehalogenase. Biochemistry 44:10360–10368Google Scholar
  107. Whitbread AK, Masoumi A, Tetlow N, Schmuck E, Coggan M, Board PG (2005) Characterization of the omega class of glutathione transferases. Methods Enzymol 401:78–99Google Scholar
  108. WHO (1986) Occupational exposures to chlorophenols. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans vol 41. IARC, Lyon, pp 319–356Google Scholar
  109. WHO (1987) Environmental Health Criteria 71, Pentachlorophenol. World Health Organization, GenevaGoogle Scholar
  110. Wieser M, Wagner B, Eberspacher J, Lingens F (1997) Purification and characterization of 2,4,6-trichlorophenol-4-monooxygenase, a dehalogenating enzyme from Azotobacter sp. strain GP1. J Bacteriol 179:202–208Google Scholar
  111. Xu L, Resing K, Lawson SL, Babbitt PC, Copley SD (1999) Evidence that pcpA encodes 2,6-dichlorohydroquinone dioxygenase, the ring cleavage enzyme required for pentachlorophenol degradation in Sphingomonas chlorophenolica strain ATCC 39723. Biochemistry 38:7659–7669Google Scholar
  112. Xun L (1996) Purification and characterization of chlorophenol 4-monooxygenase from Burkholderia cepacia AC1100. J Bacteriol 178:2645–2649Google Scholar
  113. Xun L, Orser CS (1991a) Purification, properties of pentachlorophenol hydroxylase, a flavoprotein from Flavobacterium sp. strain ATCC 39723. J Bacteriol 173:4447–4453Google Scholar
  114. Xun L, Orser CS (1991b) Purification of a Flavobacterium pentachlorophenol-induced periplasmic protein (PcpA) and nucleotide sequence of the corresponding gene (pcpA). J Bacteriol 173:2920–2926Google Scholar
  115. Xun L, Orser CS (1991c) Biodegradation of triiodophenol by cell-free extracts of a pentachlorophenol-degrading Flavobacterium sp. Biochem Biophys Res Commun 174:43–48Google Scholar
  116. Xun L, Sandvik ER (2000) Characterization of 4-hydroxyphenylacetate 3-hydroxylase (HpaB) of Escherichia coli as a reduced flavin adenine dinucleotide-utilizing monooxygenase. Appl Environ Microbiol 66:481–486Google Scholar
  117. Xun L, Wagon K (1995) Purification and properties of 2,4,5-trichlorophenoxyacetate oxygenase from Pseudomonas cepacia AC1100. Appl Environ Microbiol 61:3499–3502Google Scholar
  118. Xun L, Webster CM (2004) A monooxygenase catalyzes sequential dechlorinations of 2,4,6-trichlorophenol by oxidative and hydrolytic reactions. J Biol Chem 279:6696–6700Google Scholar
  119. Xun L, Topp E, Orser CS (1992a) Purification and characterization of a tetrachloro-p-hydroquinone reductive dehalogenase from a Flavobacterium sp. J Bacteriol 174:8003–8007Google Scholar
  120. Xun L, Topp E, Orser CS (1992b) Glutathione is the reducing agent for the reductive dehalogenation of tetrachloro-p-hydroquinone by extracts from a Flavobacterium sp. Biochem Biophy Res Comm 182:361–366Google Scholar
  121. Xun L, Topp E, Orser CS (1992c) Diverse substrate range of a Flavobacterium pentachlorophenol hydroxylase and reaction stoichiometries. J Bacteriol 174:2898–2902Google Scholar
  122. Xun L, Topp E, Orser CS (1992d) Confirmation of oxidative dehalogenation of pentachlorophenol by a Flavobacterium pentochlorophenol hydroxylase. J Bacteriol 174:5745–5747Google Scholar
  123. Xun L, Bohuslavek J, Cai M (1999) Characterization of 2,6-dichloro-p-hydroquinone 1,2-dioxygenase (PcpA) of Sphingomonas chlorophenolica ATCC 39723. Biochem Biophy Res Comm 266:322–325Google Scholar
  124. Xun L, Belchik SM, Xun R, Huang Y, Zhou H, Sanchez E (2010) S-Glutathionyl-(chloro)hydroquinone reductases: a novel class of glutathione transferases. Biochem J 428:419–427Google Scholar
  125. Zaborina O, Latus M, Eberspacher J, Golovleva LA, Lingens F (1995) Purification and characterization of 6-chlorohydroxyquinol 1,2-dioxygenase from Streptomyces rochei 303: comparison with an analogous enzyme from Azotobacter sp. strain GP1. J Bacteriol 177:229–234Google Scholar
  126. Zaborina O, Daubaras DL, Zago A, Xun L, Saido K, Klem T (1998) Novel pathway for conversion of chlorohydroxyquinol to maleylacetate in Burkholderia cepacia AC1100. J Bacteriol 180:4667–4675Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg  2012

Authors and Affiliations

  1. 1.School of Molecular BiosciencesWashington State UniversityPullmanUSA

Personalised recommendations