Identification and characterization of hydroxyquinone hydratase activities from Sphingobium chlorophenolicum ATCC 39723

Biodegradation

Volumn 16, Issue 4, 2005, Pages 353-362

  Bohuslavek, Jan ^a   Chanama, Suchart ^b,c   Crawford, Ronald L ^b   Xun, Luying ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF IDAHO   (United States)

^c CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

2,5 dihydroxyquinol; 2,5 dihydroxyquinone; Auto oxidation; Hydratase; Hydroxyquinol; Hydroxyquinone

Indexed keywords

AROMATIC COMPOUNDS; GAS CHROMATOGRAPHY; METABOLISM; STOICHIOMETRY; ULTRAVIOLET RADIATION;

2,5 DIHYDROXYQUINONE; HYDRATASE; HYDROXYQUINOL; SPHINGOBIUM CHLOROPHENOLICUM ATCC 39723;

ENZYME KINETICS;

1,2,4 BENZENETRIOL; 1,4 CYCLOHEXADIENE; 2,5 DIHYDROXYCYCLOHEX 2 ENE 1,4 DIONE; 2,5 DIHYDROXYQUINONE; BACTERIAL ENZYME; BENZENE DERIVATIVE; ENZYME; HYDROLYASE; HYDROXYQUINONE; HYDROXYQUINONE HYDRATASE; OXYGEN; QUINONE DERIVATIVE; QUINONE HYDRATASE; UNCLASSIFIED DRUG; WATER;

ENZYME ACTIVITY;

ABSORPTION SPECTROSCOPY; ARTICLE; AUTOOXIDATION; BACTERIUM; CATALYSIS; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; ENZYME ANALYSIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MICROBIAL METABOLISM; NONHUMAN; SPHINGOBIUM CHLOROPHENOLICUM; STOICHIOMETRY; ULTRAVIOLET RADIATION;

BENZOQUINONES; BIODEGRADATION, ENVIRONMENTAL; HYDRO-LYASES; PENTACHLOROPHENOL; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPHINGOMONADACEAE;

SPHINGOBIUM CHLOROPHENOLICUM;

EID: 18044369926     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10532-004-2058-5     Document Type: Article

References (47)

1. S Aftergut 1996 Photoconducting layer of electrostatic copiers, Belg 032 670
2. JH Apajalahti MS Salkinoja-Salonen 1987 Complete dechlorination of tetrachlorohydroquinone by cell extracts of pentachlorophenol-induced Rhodococcus chlorophenolicus J. Bacteriol. 169 5125 5130
3. SM Armstrong TR Patel 1993 1, 3, 5-Trihydroxybenzene biodegradation by Rhodococcus sp BPG-8. Can. J. Microbiol. 39 175 179
4. SM Armstrong TR Patel M Whalen 1993 Detoxification mechanisms for 1, 2, 4-benzenetriol employed by a Rhodococcus sp BPG-8. Arch. Microbiol. 159 136 140
5. CL Bering PL Bustamante PA Loach 1981 Inhibition of the primary photochemical events in Rhodospirillum rubrum by ubiquinone analogs Isr. J. Biochem. 21 251 258
6. A Brune B Schink 1990 Pyrogallol-to-phloroglucinol conversion and other hydroxyl-transfer reactions catalyzed by cell extracts of Pelobacter acidigallici. J. Bacteriol. 172 1070 1076
7. JA Buswell KE Eriksson 1979 Aromatic ring cleavage by the white-rot fungus Sporotrichum pulverulentum FEBS Lett. 104 258 260
8. PJ Chapman DW Ribbons 1976 Metabolism of resorcinylic compounds by bacteria: alternative pathways for resorcinol catabolism in Pseudomonas putida J. Bacteriol. 125 985 998
9. A Chauhan SK Samantha RK Jain 2000 Degradation of 4-nitrocatechol by Burkholderia cepacia: a plasmid-encoded novel pathway J. Appl. Microbiol. 88 764 772
10. DL Daubaras K Saido AM Chakrabarty 1996 Purification of hydroxyquinol 1: 2-dioxygenase and maleylacetate reductase: the lower pathway of 2: 4: 5-trichlorophenoxyacetic acid metabolism by Burkholderia cepacia AC1100 Appl. Environ. Microbiol. 62 4276 4279
11. N Farfan E Ortega R Contreras 1986 New heterocycles derived from a simultaneous substitution and reductive acetylation of 2, 5-dihydroxy-1, 4-benzoquinone by N-containing heterocycles. J. Heterocyclic Chem. 23 1609 1612
12. A Gaal H. Y. Neujahr. 1979 Metabolism of phenol and resorcinol in Trichosporon cutaneum J. Bacteriol. 137 13 21
13. C Gallus B Schink 1998 Anaerobic degradation of a-resorcylate by Thauera aromatica strain AR-1 proceeds via oxidation and decarboxylation of hydroxyhydroquinone. Arch. Microbiol. 169 333 338
14. CJ Gogek 1965 Stain-removing compositions, U.S US 3 207 694
15. F Guillen MJ Martinez C Munoz AT Martinez 1997 Quinone redox cycling in the ligninolytic fungus Pleurotus eryngii leading to extracellular production of superoxide anion radical Arch. Biochem. Biophys. 339 190 199
16. JD Haddock JG Ferry 1993 Initial steps in the anaerobic degradation of 3, 4, 5-trihydroxybenzoate by Eubacterium oxidoreducens: characterization of mutants and role of 1, 2, 3, 5-tetrahydroxybenzene J. Bacteriol. 175 669 673
17. K Hiramoto X Li M Makimoto T Kato K Kikugawa 1998 Identification of hydroxyhydroquinone in coffee as a generator of reactive oxygen species that break DNA single strands. Mutat. Res. 419 43 51
18. H Iwaki Y Fukuyama K Matsui 1985 1, 4-benzoquinone derivatives and benzene derivatives, Eur 995 Pat. Appl. EP 151
19. KH Jones PW Trudgill DJ Hopper 1995 Evidence of two pathways for the metabolism of phenol by Aspergillus fumigatus Arch. Microbiol. 163 176 181
20. DR Knapp 1979 Handbook of analytical derivatization reactions. John Wiley & Sons Inc. New York
21. JH Kolaian 1967 Aqueous drilling fluids, U.S US 3 586 628
22. LR Krumholz MP Bryant 1988 Characterization of the pyrogallol- phloroglucinol isomerase of Eubacterium oxidoreductans J. Bacteriol. 170 2472 2479
23. UK Laemmli 1970 Cleavage of structural proteins during assembly of the head of bacteriophage T4 Nature (London) 227 680 685
24. G Lang A Malaval JF Grollier G Rosenbaum 1983 Benzoquinone derivatives for direct hair dyes Ger Offen. DE 3 244 454
25. M Latus H Seitz J Eberspächer F Lingens 1995 Purification and characterization of hydroxyquinol 1, 2-dioxygenase from Azobacter sp. strain GP1. Appl. Environ. Microbiol. 61 2453 2460
26. A Li SB Bandy SS Tsang AJ Davidson 2000 DNA-breaking versus DNA-protecting activity of four phenolic compounds in vitro Free Radic. Res. 33 551 566
27. Matusevitch PA, Krul LP, Zvonok AM & Skorobogataya LI (1982) Stabilization of polycaprolactam yarns and films, U.S.S.R. SU 931: 828
28. LV Natanajan RE Blankenship 1983 Free energy dependence of the quenching of chlorophyll a fluorescence by substituted quinones Photochem. Photobiol. 37 329 336
29. Y Ohtsubo K Miyauchi K Kanda T Hatta H Kiyohara T Senda Y Nagata Y Mitsui M Takagi 1999 PcpA, which is involved in the degradation of pentachlorophenol in Sphingomonas chlorophenolica ATCC39723, is a novel type of ring-cleavage dioxygenase. FEBS Lett. 459 395 598
30. B Philipp B Schink 1998 Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1, 3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius. J. Bacteriol. 180 3644 3649
31. B Philipp B Schink 2000 Two distinct pathways for anaerobic degradation of aromatic compounds in the denitrifying bacterium Thauera aromatica strain AR-1. Arch. Microbiol. 173 91 96
32. GV Reddy MD Gelpke MH Gold 1998 Degradation of 2, 4, 6-trichlorophenol by Phanerochaete chrysosporium: involvement of reductive dechlorination J. Bacteriol. 180 5159 5164
33. W Reichenbecher B Philipp MJ Suter B Schink 2000 Hydroxyhydroquinone reductase, the initial enzyme involved in the degradation of hydroxyhydroquinone (1, 2, 4-trihydroxybenzene) by Desulfovibrio inopinatus. Arch. Microbiol. 173 206 212
34. W Reichenbecher B Schink 1999 Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici. Biochim. Biophys. Acta. 1430 245 253
35. S Rieble DK Joshi MH Gold 1994 Purification and characterization of a 1, 2, 4-trihydroxybenzene 1, 2-dioxygenase from the basidiomycete Phanerochaete chrysosporium J. Bacteriol. 176 4838 4844
36. J Robinson JM Cooper 1970 Method of determining oxygen concentrations in biological media, suitable for calibration of the oxygen electrode Anal. Biochem. 33 390 399
37. DL Saber RL Crawford 1985 Isolation and characterization of Flavobacterium strains that degrade pentachlorophenol Appl. Environ. Microbiol. 50 1512 1518
38. JC Spain DT Gibson 1991 Pathway for biodegradation of p-nitrophenol in a Moraxella sp Appl. Environ. Microbiol. 57 812 819
39. A Stolz H-J Knackmuss 1993 Degradation of 2,4-dihydroxybenzoate by Pseudomonas sp BN9. FEMS Microbiol. Lett. 108 219 224
40. T Suzuki K Hibino M Murai T Fujita 1984 Magnetic recording medium, U.S US 4 425 404
41. IS-Y. Sze S Dagley 1984 Properties of salicylate hydroxylase and hydroxyquinol 1,2-dioxygenase purified from Trichosporon cutaneum. J. Bacteriol. 159 353 359
42. JS Uotila VH Kitunen T Coote T Saastamoinen M Salkinoja-Salonen JH Apajalahti 1995 Metabolism of halohydroquinones in Rhodococcus chlorophenolicus PCP-1 Biodegradation 6 119 126
43. K Valli H Wariishi MH Gold 1992 Degradation of 2,7-dichlorodibenzo-p- dioxin by the lignin-degrading Basidiomycete Phanerochaete chrysosporium J. Bacteriol. 174 2131 2137
44. L Xun J Bohuslavek M Cai 1999 Characterization of 2,6-dichloro-p- hydroquinone 1,2-dioxygenase (PcpA) of Sphingomonas chlorophenolica ATCC 39723. Biochem. Biophy. Res. Comm. 266 322 325
45. L Xun ER Sandvik 2000 Characterization of 4-hydroxyphenylacetate 3-hydroxylase (HpaB) of Escherichia coli as a reduced flavin adenine dinucleotide-utilizing monooxygenase Appl. Environ. Microbiol. 66 481 486
46. O Zaborina DL Daubaras A Zago L Xun K Saido T Klem D Nikolic AM. Chakrabarty 1998 Novel pathway for conversion of chlorohydroxyquinol to maleylacetate in Burkholderia cepacia AC1100 J. Bacteriol. 180 4667 4675
47. O Zaborina M Latus J Eberspacher LA Golovleva F Lingens 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. 177 229 234