Enzyme systems for biodegradation of polychlorinated dibenzo-p-dioxins

Applied Microbiology and Biotechnology

Volumn 88, Issue 1, 2010, Pages 23-30

  Sakaki, Toshiyuki ^a   Munetsuna, Eiji ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Bioremediation; Dioxin; Enzyme; Metabolism; Microorganism

Indexed keywords

ACTIVE CENTER; AEROBIC CONDITION; CYTOCHROME P450; DEHALOGENASE; DIOXIN; DIOXYGENASES; ELECTRON TRANSPORT CHAIN; ENZYMATIC PROPERTIES; ENZYME SYSTEMS; LIGNIN PEROXIDASE; POLYCHLORINATED DIBENZO- P - DIOXINS; POLYCHLORINATED DIBENZOFURANS; PRACTICAL USE; PROTEIN ENGINEERING; RECOMBINANT MICROORGANISM; SITE DIRECTED MUTAGENESIS; TERTIARY STRUCTURES; TETRACHLORODIBENZO P DIOXINS;

BIOCHEMICAL ENGINEERING; BIODEGRADATION; BIOREMEDIATION; CATALYSTS; CHLORINE; DEGRADATION; GENETIC ENGINEERING; LIGNIN; METABOLISM; METAL IONS; MICROORGANISMS; POLLUTION;

ENZYMES;

ANGULAR DIOXYGENASE; CYTOCHROME P450; DEHALOGENASE; DIOXYGENASE; ENZYME; HYDROLASE; LIGNIN PEROXIDASE; METAL ION; POLYCHLORINATED DIBENZODIOXIN; UNCLASSIFIED DRUG;

BIODEGRADATION; BIOREMEDIATION; CYTOCHROME; ENZYME ACTIVITY; GENETIC ENGINEERING; METABOLISM; PCDD; PROTEIN; RECOMBINATION; SOIL POLLUTION;

BIODEGRADATION; ENZYME STRUCTURE; FUNGUS; NONHUMAN; PROKARYOTE; PROTEIN ENGINEERING; RESPIRATORY CHAIN; SHORT SURVEY; SITE DIRECTED MUTAGENESIS;

AEROBIOSIS; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; DIOXYGENASES; ENZYMES; HYDROLASES; PEROXIDASES; RECOMBINANT PROTEINS; TETRACHLORODIBENZODIOXIN;

EID: 77955850991     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-2765-2     Document Type: Short Survey

References (61)

1. L Adrian U Szewzyk J Wecke H Gorisch 2000 Bacterial dehalorespiration with chlorinated benzenes Nature 408 580 583 10.1038/35046063 1:CAS:528:DC%2BD3cXovFWrsLc%3D
2. J Armengaud KN Timmis 1997 Molecular characterization of Fdx1, a putidaredoxin-type [2Fe-2S] ferredoxin able to transfer electrons to the dioxin dioxygenase of Sphingomonas sp. RW1 Eur J Biochem 247 833 842 10.1111/j.1432-1033.1997.00833.x 1:CAS:528:DyaK2sXlsVCmtLY%3D
3. J Armengaud KN Timmis 1998 The reductase RedA2 of the multi-component dioxin dioxygenase system of Sphingomonas sp. RW1 is related to class-I cytochrome P450-type reductases Eur J Biochem 253 437 444 10.1046/j.1432-1327. 1998.2530437.x 1:CAS:528:DyaK1cXis1Khu7o%3D
4. J Armengaud B Happe KN Timmis 1998 Genetic analysis of dioxin dioxygenase of Sphingomonas sp. strain RW1: catabolic genes dispersed on the genome J Bacteriol 180 3954 3966 1:CAS:528:DyaK1cXlt1Chtrg%3D
5. J Armengaud J Gaillard KN Timmis 2000 A second [2Fe-2S] ferredoxin from Sphingomonas sp. strain RW1 can function as an electron donor for the dioxin dioxygenase J Bacteriol 182 2238 2244 10.1128/JB.182.8.2238-2244.2000 1:CAS:528:DC%2BD3cXitlGgur8%3D
6. JA Bumpus M Tien D Wright SD Aust 1985 Oxidation of persistent environmental pollutants by a white rot fungus Science 228 1434 1436 10.1126/science.3925550 1:CAS:528:DyaL2MXksFylsrY%3D
7. M Bunge L Adrian A Kraus M Opel WG Lorenz JR Andreesen H Gorisch U Lechner 2003 Reductive dehalogenation of chlorinated dioxins by an anaerobic bacterium Nature 421 357 360 10.1038/nature01237 1:CAS:528: DC%2BD3sXlsVagug%3D%3D
8. AB Carmichael LL Wong 2001 Protein engineering of Bacillus megaterium CYP102. The oxidation of polycyclic aromatic hydrocarbons Eur J Biochem 268 3117 3125 10.1046/j.1432-1327.2001.02212.x 1:CAS:528:DC%2BD3MXktVSkur0%3D
9. YS Chang 2008 Recent developments in microbial biotransformation and biodegradation of dioxins J Mol Microbiol Biotechnol 15 152 171 1:CAS:528:DC%2BD1cXptlyhtr8%3D
10. X Dong S Fushinobu E Fukuda T Terada S Nakamura K Shimizu H Nojiri T Omori H Shoun T Wakagi 2005 Crystal structure of the terminal oxygenase component of cumene dioxygenase from Pseudomonas fluorescens IP01 J Bacteriol 187 2483 2490 10.1128/JB.187.7.2483-2490.2005 1:CAS:528:DC%2BD2MXjt1KqsL4%3D
11. SL Edwards R Raag H Wariishi MH Gold TL Poulos 1993 Crystal structure of lignin peroxidase Proc Natl Acad Sci USA 90 750 754 10.1073/pnas.90.2.750 1:CAS:528:DyaK3sXpslSmtA%3D%3D
12. DT Gibson RE Parales 2000 Aromatic hydrocarbon dioxygenases in environmental biotechnology Curr Opin Biotechnol 11 236 243 10.1016/S0958- 1669(00)00090-2 1:CAS:528:DC%2BD3cXksVGks74%3D
13. H Habe JS Chung JH Lee K Kasuga T Yoshida H Nojiri T Omori 2001 Degradation of chlorinated dibenzofurans and dibenzo-p-dioxins by two types of bacteria having angular dioxygenases with different features Appl Environ Microbiol 67 3610 3617 10.1128/AEM.67.8.3610-3617.2001 1:CAS:528: DC%2BD3MXlvFSlu7c%3D
14. H Harms H Wilkes V Sinnwell R-M Wittich K Figge W Francke P Fortnagel 1991 Transformation of 3-chlorodibenzofuran by Pseudomonas sp. HH69 FEMS Microbiol Lett 65 25 29 1:STN:280:DyaK3MzktVSrtw%3D%3D
15. HB Hong YS Chang IH Nam P Fortnagel S Schmidt 2002 Biotransformation of 2, 7-dichloro- and 1, 2, 3, 4-tetrachlorodibenzo-p-dioxin by Sphingomonas wittichii RW1 Appl Environ Microbiol 68 2584 2588 10.1128/AEM.68.5.2584-2588. 2002 1:CAS:528:DC%2BD38XjsFGqu78%3D
16. T Holscher R Krajmalnik-Brown KM Ritalahti F Von Wintzingerode H Gorisch FE Loffler L Adrian 2004 Multiple nonidentical reductive-dehalogenase-homologous genes are common in Dehalococcoides Appl Environ Microbiol 70 5290 5297 10.1128/AEM.70.9.5290-5297.2004
17. K Hu NJ Bunce 1999 Metabolism of polychlorinated dibenzo-p-dioxins and related dioxin-like compounds J Toxicol Environ Health B Crit Rev 2 183 210 10.1080/109374099281214 1:CAS:528:DyaK1MXislShsr4%3D
18. K Hu NJ Bunce 1999 Metabolism of polychlorinated dibenzo-p-dioxins by rat liver microsomes J Biochem Mol Toxicol 13 307 315 10.1002/(SICI)1099-0461(1999) 13:6<307::AID-JBT4>3.0.CO;2-P 1:CAS:528:DyaK1MXlvVWitrw%3D
19. DK Joshi MH Gold 1994 Oxidation of dibenzo-p-dioxin by lignin peroxidase from the basidiomycete Phanerochaete chrysosporium Biochemistry 33 10969 10976 10.1021/bi00202a016 1:CAS:528:DyaK2cXlsFSktrc%3D
20. N Kasai S Ikushiro R Shinkyo K Yasuda S Hirosue A Arisawa H Ichinose H Wariishi T Sakaki 2010 Metabolism of mono- and dichloro-dibenzo-p-dioxins by Phanerochaete chrysosporium cytochromes P450 Appl Microbiol Biotechnol 86 773 780 10.1007/s00253-009-2413-x 1:CAS:528:DC%2BC3cXit1ams7g%3D
21. B Kauppi K Lee E Carredano RE Parales DT Gibson H Eklund S Ramaswamy 1998 Structure of an aromatic-ring-hydroxylating dioxygenase-naphthalene 1, 2-dioxygenase Structure 6 571 586 10.1016/S0969-2126(98)00059-8 1:CAS:528:DyaK1cXjvFWltbk%3D
22. PC Kearny EA Woolson CP Ellington Jr 1972 Persistence and metabolism of chlorodioxins in soils Environ Sci Technol 6 1017 1019 10.1021/es60071a010
23. T Keim W Francke S Schmidt P Fortnagel 1999 Catabolism of 2, 7-dichloro- and 2, 4, 8-trichlorodibenzofuran by Sphingomonas sp. strain RW1 J Ind Microbiol Biotechnol 23 359 363 10.1038/sj.jim.2900739 1:CAS:528:DyaK1MXotVKitrg%3D
24. LF Larrondo P Canessa R Vicuna P Stewart A Vanden Wymelenberg D Cullen 2007 Structure and transcriptional impact of divergent repetitive elements inserted within Phanerochaete chrysosporium strain RP-78 genes Mol Genet Genomics 277 43 55 10.1007/s00438-006-0167-z 1:CAS:528:DC%2BD28XhtlWntbzO
25. F Matsumura HJ Benezet 1973 Studies on the bioaccumulation and microbial degradation of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin Environ Health Perspect 5 253 258 10.2307/3428136 1:CAS:528:DyaE2MXmvV2rtQ%3D%3D
26. F Matsuzaki H Wariishi 2004 Functional diversity of cytochrome P450s of the white-rot fungus Phanerochaete chrysosporium Biochem Biophys Res Commun 324 387 393 10.1016/j.bbrc.2004.09.062 1:CAS:528:DC%2BD2cXot1WktLY%3D
27. L Monna T Omori T Kodama 1993 Microbial degradation of dibenzofuran, fluorene, and dibenzo-p-dioxin by Staphylococcus auriculans DBF63 Appl Environ Microbiol 59 285 289 1:CAS:528:DyaK3sXpslOktg%3D%3D
28. IH Nam YM Kim S Schmidt YS Chang 2006 Biotransformation of 1, 2, 3-tri- and 1, 2, 3, 4, 7, 8-hexachlorodibenzo-p-dioxin by Sphingomonas wittichii strain RW1 Appl Environ Microbiol 72 112 116 10.1128/AEM.72.1.112-116.2006 1:CAS:528:DC%2BD28XmtFantQ%3D%3D
29. A Neumann G Wohlfarth G Diekert 1996 Purification and characterization of tetrachloroethene reductive dehalogenase from Dehalospirillum multivorans J Biol Chem 271 16515 16519 10.1074/jbc.271.28.16515 1:CAS:528:DyaK28Xkt1equrk%3D
30. A Neumann G Wohlfarth G Diekert 1998 Tetrachloroethene dehalogenase from Dehalospirillum multivorans: cloning, sequencing of the encoding genes, and expression of the pceA gene in Escherichia coli J Bacteriol 180 4140 4145 1:CAS:528:DyaK1cXlsVahsrk%3D
31. H Nojiri Y Ashikawa H Noguchi JW Nam M Urata Z Fujimoto H Uchimura T Terada S Nakamura K Shimizu T Yoshida H Habe T Omori 2005 Structure of the terminal oxygenase component of angular dioxygenase, carbazole 1, 9a-dioxygenase J Mol Biol 351 355 370 10.1016/j.jmb.2005.05.059 1:CAS:528:DC%2BD2MXmsVOrtbc%3D
32. T Omura 2010 Structural diversity of cytochrome P450 enzyme system J Biochem 147 297 306 10.1093/jb/mvq001 1:CAS:528:DC%2BC3cXitlaqurk%3D
33. K Orihara T Yamazaki R Shinkyo T Sakaki K Inouye A Tsukamoto J Sugiura K Shishido 2005 Rat cytochrome P450-mediated transformation of dichlorodibenzo-p-dioxins by recombinant white-rot basidiomycete Coriolus hirsutus Appl Microbiol Biotechnol 69 22 28 10.1007/s00253-005-1943-0 1:CAS:528:DC%2BD2MXht1Cqt7bK
34. JR Parsons JA De Bruijne AR Weiland 1998 Biodegradation pathway of 2-chlorodibenzo-p-dioxin and 2-chlorodibenzofuran in the biphenyl-utilising strain JB1 Chemosphere 37 1915 1922 10.1016/S0045-6535(98)00258-6 1:CAS:528:DyaK1cXmvV2ktb8%3D
35. D Paul G Pandey RK Jain 2005 Suicidal genetically engineered microorganisms for bioremediation: need and perspectives Bioessays 27 563 573 10.1002/bies.20220 1:CAS:528:DC%2BD2MXksFOhsrc%3D
36. E Petroske JK Huwe VJ Feil GL Larsen 1997 Identification of NIH-shifted metabolites of 1, 3, 7, 8-tetrachlorodibenzo-p-dioxin in the rat by NMR comparison with synthesized isomers Chemosphere 34 1549 1555 10.1016/S0045-6535(97)00450-5 1:CAS:528:DyaK2sXitF2qsrw%3D
37. Philippi M, Krasnobajew V, Zeyer J, Hutter R (1981) Fate of TCDD in microbial cultures and in soil under laboratory conditions. In: Leisinger T, Hutter R, Cook AM, Nuesch J (eds) Microbaial degradation of xenobiotics and recalcitrant compounds. Academic, New York London, pp 221-233
38. M Philippi J Schmid HK Wipf R Hutter 1982 A microbial metabolite of TCDD Experientia 38 659 661 10.1007/BF01964077 1:CAS:528:DyaL38Xks1Ogt7Y%3D
39. H Poiger HR Buser H Weber U Zweifel C Schlatter 1982 Structure elucidation of mammalian TCDD-metabolites Experientia 38 484 486 10.1007/BF01952652 1:CAS:528:DyaL38XktVWkt7c%3D
40. JF Quensen F Matsumura 1983 Oxidative degradation of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin by microorganisms Environ Toxicol Chem 2 261 268 1:CAS:528:DyaL2cXot1Giuw%3D%3D
41. T Sakaki R Shinkyo T Takita M Ohta K Inouye 2002 Biodegradation of polychlorinated dibenzo-p-dioxins by recombinant yeast expressing rat CYP1A subfamily Arch Biochem Biophys 401 91 98 10.1016/S0003-9861(02)00036-X 1:CAS:528:DC%2BD38XksF2ksLo%3D
42. G Schreiner T Wiedmann H Schimmel K Ballschmiter 1997 Influence of the substitution pattern on the microbial degradation of mono- to tetrachlorinated dibezo-p-dioxins and dibenzofurans Chemosphere 34 1315 1331 10.1016/S0045- 6535(97)00429-3 1:CAS:528:DyaK2sXitF2rurw%3D
43. W Schumacher C Holliger AJ Zehnder WR Hagen 1997 Redox chemistry of cobalamin and iron-sulfur cofactors in the tetrachloroethene reductase of Dehalobacter restrictus FEBS Lett 409 421 425 10.1016/S0014-5793(97)00520-6 1:CAS:528:DyaK2sXjslKls74%3D
44. S Shary AN Kapich EA Panisko JK Magnuson D Cullen KE Hammel 2008 Differential expression in Phanerochaete chrysosporium of membrane-associated proteins relevant to lignin degradation Appl Environ Microbiol 74 7252 7257 10.1128/AEM.01997-08 1:CAS:528:DC%2BD1cXhsVymsb7P
45. R Shinkyo T Sakaki M Ohta K Inouye 2003 Metabolic pathways of dioxin by CYP1A1: species difference between rat and human CYP1A subfamily in the metabolism of dioxins Arch Biochem Biophys 409 180 187 10.1016/S0003-9861(02) 00366-1 1:CAS:528:DC%2BD38Xps1Witrg%3D
46. R Shinkyo T Sakaki T Takita M Ohta K Inouye 2003 Generation of 2, 3, 7, 8-TCDD-metabolizing enzyme by modifying rat CYP1A1 through site-directed mutagenesis Biochem Biophys Res Commun 308 511 517 10.1016/S0006-291X(03)01439-6 1:CAS:528:DC%2BD3sXmt1Wqsr0%3D
47. R Shinkyo M Kamakura S Ikushiro K Inouye T Sakaki 2006 Biodegradation of dioxins by recombinant Escherichia coli expressing rat CYP1A1 or its mutant Appl Microbiol Biotechnol 72 584 590 10.1007/s00253-005-0286-1 1:CAS:528: DC%2BD28XotlChs78%3D
48. WT Sulistyaningdyah J Ogawa QS Li R Shinkyo T Sakaki K Inouye RD Schmid S Shimizu 2004 Metabolism of polychlorinated dibenzo-p-dioxins by cytochrome P450 BM-3 and its mutant Biotechnol Lett 26 1857 1860 10.1007/s10529-004-5317-y 1:CAS:528:DC%2BD2MXnt1Sjsw%3D%3D
49. HL Tai JH Mcreynolds JA Goldstein HP Eugster C Sengstag WL Alworth JR Olson 1993 Cytochrome P4501A1 mediates the metabolism of 2, 3, 7, 8-tetrachlorodibenzofuran in the rat and human Toxicol Appl Pharmacol 123 34 42 10.1006/taap.1993.1218 1:CAS:528:DyaK2cXpvVKksA%3D%3D
50. S Takada M Nakamura T Matsueda R Kondo K Sakai 1996 Degradation of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans by the white rot fungus Phanerochaete sordida YK-624 Appl Environ Microbiol 62 4323 4328 1:CAS:528:DyaK28Xnt1agur4%3D
51. Tulp MT, Hutzinger O (1978) Rat metabolism of polychlorinated dibenzo-p-dioxins. Chemosphere 9:761-778
52. 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 1:CAS:528:DyaK38XisFSjs7k%3D
53. BA Van De Pas H Smidt WR Hagen J Van Der Oost G Schraa AJ Stams WM De Vos 1999 Purification and molecular characterization of ortho-chlorophenol reductive dehalogenase, a key enzyme of halorespiration in Desulfitobacterium dehalogenans J Biol Chem 274 20287 20292 10.1074/jbc.274.29.20287
54. FX Van Leeuwen M Feeley D Schrenk JC Larsen W Farland M Younes 2000 Dioxins: WHO's tolerable daily intake (TDI) revisited Chemosphere 40 1095 1101 10.1016/S0045-6535(99)00358-6
55. AS Waller R Krajmalnik-Brown FE Loffler EA Edwards 2005 Multiple reductive-dehalogenase-homologous genes are simultaneously transcribed during dechlorination by Dehalococcoides-containing cultures Appl Environ Microbiol 71 8257 8264 10.1128/AEM.71.12.8257-8264.2005 1:CAS:528:DC%2BD2MXhtlehtb%2FN
56. CT Ward F Matsumura 1978 Fate of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) in a model aquatic environment Arch Environ Contam Toxicol 7 349 357 10.1007/BF02332062 1:CAS:528:DyaE1cXmtV2qsb4%3D
57. H Wilkes R Wittich KN Timmis P Fortnagel W Francke 1996 Degradation of chlorinated dibenzofurans and dibenzo-p-dioxins by Sphingomonas sp. strain RW1 Appl Environ Microbiol 62 367 371 1:CAS:528:DyaK28XovVCnuw%3D%3D
58. R-M Wittich 1998 Degradation of dioxin-like compounds by microorganisms Appl Microbiol Biotechnol 49 489 499 10.1007/s002530051203 1:CAS:528: DyaK1cXkt1Klsbs%3D
59. R-M Wittich H Wilkes V Sinnwell W Francke P Fortnagel 1992 Metabolism of dibenzo-p-dioxin by Sphingomonas sp. strain RW1 Appl Environ Microbiol 58 1005 1010 1:CAS:528:DyaK38XhvFSku7o%3D
60. R-M Wittich C Strompl ER Moore R Blasco KN Timmis 1999 Interaction of Sphingomonas and Pseudomonas strains in the degradation of chlorinated dibenzofurans J Ind Microbiol Biotechnol 23 353 358 10.1038/sj.jim.2900740 1:CAS:528:DyaK1MXotVKitrs%3D
61. JS Yadav H Doddapaneni V Subramanian 2006 P450ome of the white rot fungus Phanerochaete chrysosporium: structure, evolution and regulation of expression of genomic P450 clusters Biochem Soc Trans 34 1165 1169 10.1042/BST0341165 1:CAS:528:DC%2BD28XhtFKgtb7J