Mineralization and transformation of monofluorophenols by Pseudonocardia benzenivorans

Applied Microbiology and Biotechnology

Volumn 87, Issue 4, 2010, Pages 1569-1577

  Kim, Eun Ju ^a   Jeon, Jong Rok ^a   Kim, Young Mo ^a,b   Murugesan, Kumarasamy ^a   Chang, Yoon Seok ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

4 Fluorophenol; Biodegradation; Monofluorophenols; Pseudonocardia benzenivorans

Indexed keywords

2-FLUOROPHENOL; 4-FLUOROPHENOL; COMPREHENSIVE INFORMATION; DIOXYGENASES; ENZYMATIC ASSAY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ORTHO-CLEAVAGE PATHWAY; PSEUDONOCARDIA; TRANSFORMATION PRODUCTS; WHOLE-CELL EXTRACTS;

BIODEGRADATION; CELL CULTURE; DEGRADATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MICROBIOLOGY; PHENOLS; REACTION INTERMEDIATES; WAVELET TRANSFORMS;

GAS CHROMATOGRAPHY;

3 FLUOROPYROCATECHOL; 4 FLUOROCATECHOL; 4 FLUOROPHENOL; CATECHOL; CATECHOL 1,2 DIOXYGENASE; MONOFLUOROPHENOL DERIVATIVE; PHENOL; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

BACTERIUM; BIODEGRADATION; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; GENE EXPRESSION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METABOLITE; MINERALIZATION; TRANSFORMATION;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PSEUDONOCARDIA BENZENIVORANS; PSEUDONOCARDIACEAE; ACTINOMYCETALES; BIOREMEDIATION; BIOTRANSFORMATION; METABOLISM;

ACTINOMYCETALES; BIODEGRADATION, ENVIRONMENTAL; BIOTRANSFORMATION; PHENOLS;

BACTERIA (MICROORGANISMS); PSEUDONOCARDIA BENZENIVORANS;

EID: 77955549478     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-010-2647-7     Document Type: Article

References (35)

1. I Bartels HJ Knackmuss W Reineke 1984 Suicide inactivation of catechol 2, 3-dioxygenase from Pseudomonas putida mt-2 by 3-halocatechols Appl Environ Microbiol 47 500 505 1:CAS:528:DyaL2cXitVGmtr4%3D
2. MG Boesmna TY Dinarieva WJ Middlehoven WJH Van Berkel J Doran J Vervoort IMCM Rietjens 1998 19F nuclear magnetic resonance as a tool to investigate microbial degradation of fluorophenols to fluorocatechols and fluoromuconates Appl Environ Microbiol 64 1256 1263
3. MG Boersma IP Solyanikova WJH Van Berkel J Vervoort L Golovleva IMCM Rietjens 2001 19F NMR metabolomics for the elucidation of microbial degradation pathways of fluorophenols J Ind Microbiol Biotechnol 26 22 34 10.1038/sj.jim.7000027 1:CAS:528:DC%2BD3MXisVCns7s%3D (Pubitemid 32568452)
4. VS Bondar MG Boersma EL Golovlev J Vervoort WJH Van Berkel ZI Finkelstein IP Solyanikova LA Golovleva IMCM Rietjens 1998 19F NMR study on the biodegradation of fluorophenols by various Rhodococcus species Biodegradation 9 475 486 10.1023/A:1008391906885 1:CAS:528:DyaK1MXltVKis7s%3D (Pubitemid 29202815)
5. VS Bondar MG Boersma WJH Van Berkel ZI Finkelstein EL Golovlev BP Baskunov LA Vervoort Golovleva IMCM Rietjens 1999 Preferential oxidative dehalogenation upon conversion of 2-halophenols by Rhodococcus opacus 1G FEMS Microbiol Lett 181 73 82 10.1111/j.1574-6968.1999.tb08828.x 1:CAS:528: DyaK1MXntlemsbY%3D
6. JB Broderick 1999 Catechol dioxygenases Essays Biochem 34 173 189 1:CAS:528:DC%2BD3cXlslajuw%3D%3D
7. DR Buhler F Unlu DR Thakker TJ Slaqa AH Conney AW Wood RL Chang W Levin DM Jerina 1983 Effect of a 6-fluoro substituent on the metabolism and biological activity of benzo(a)pyrene Cancer Res 43 1541 1549 1:CAS:528:DyaL3sXhslCmu7c%3D
8. MF Carvalho CCT Alves MIM Ferreira P De Marco PML Castro 2002 Isolation and initial characterization of a bacterial consortium able to mineralize fluorobenzene Appl Environ Microbiol 68 102 105 10.1128/AEM.68.1.102-105.2002 1:CAS:528:DC%2BD38Xjt1Wgsg%3D%3D (Pubitemid 34031169)
9. MF Carvalho MIM Ferreira IS Moreira PML Castro DB Janssen 2006 Degradation of fluorobenzene by Rhizobiales strain F11 via ortho cleavage of 4-fluorocatechol and catechol Appl Environ Microbiol 72 7413 7417 10.1128/AEM.01162-06 1:CAS:528:DC%2BD28Xht1GksrvL (Pubitemid 44748469)
10. Z Chaojie Z Qi C Ling Y Yuan Y Hui 2007 Degradation of mono-fluorophenols by an acclimated activated sludge Biodegradation 18 51 61 10.1007/s10532-005- 9035-5 (Pubitemid 46020889)
11. E Dorn HJ Knackmuss 1978 Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1, 2 dioxygenation of catechol Biochem J 174 85 94 1:CAS:528:DyaE1MXkvFSjtw%3D%3D (Pubitemid 8378831)
12. KH Engesser MA Rubio DW Ribbons 1988 Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 4-trifluoromethyl(TFM)-benzoate by 4-isopropylbenzoate grown Pseudomonas putida JT strains Arch Microbiol 149 198 206 10.1007/BF00422005 1:CAS:528:DyaL1cXhs1Cms70%3D
13. MIM Ferreira JR Marchesi DB Janssen 2008 Degradation of 4-fluorophenol by Arthrobacter sp. strain IF1 Appl Microbiol Biotechnol 78 709 717 10.1007/s00253-008-1343-3 1:CAS:528:DC%2BD1cXjtVKgsL0%3D
14. ZI Finkelstein BP Baskunov MG Boersma J Vervoort EL Golovlev WJH Van Berkel LA Golovleva IMCM Rietjens 2000 Identification of fluoropyrogallols as new intermediates in biotransformation of monofluorophenols in Rhodococcus opacus 1cp Appl Environ Microbiol 66 2148 2153 10.1128/AEM.66.5.2148-2153.2000 1:CAS:528:DC%2BD3cXjtV2lu7k%3D (Pubitemid 30253745)
15. P Fortnagel H Harms RM Wittich S Krohn H Meyer V Sinnwell H Wilkes W Francke 1990 Metabolism of dibenzofuran by Pseudomonas sp. strain HH69 and the mixed culture HH27 Appl Environ Microbiol 56 1148 1156 1:CAS:528: DyaK3cXksFGmurc%3D
16. DT Gibson 1968 Microbial degradation of aromatic compounds Science 161 1093 1097 10.1126/science.161.3846.1093 1:CAS:528:DyaF1cXltVeqtL4%3D
17. SN Gorlatov LA Golovleva 1992 Effect of cosubstrates on the dechlorination of selected chlorophenolic compounds by Rhodococcus erythropolis 1CP J Basic Microbol 32 177 184 10.1002/jobm.3620320306 1:CAS:528: DyaK38Xmt12rsLk%3D
18. G Gurujeyalakshmi P Oriel 1989 Isolation of phenol-degrading Bacillus stearothermophilus and partial characterization of the phenol hydroxylase Appl Environ Microbiol 55 500 502 1:CAS:528:DyaL1MXhtlWjsbk%3D
19. M Haggblom 1990 Mechanisms of bacterial degradation and transformation of chlorinated monoaromatic compounds J Basic Microbiol 30 115 141 10.1002/jobm.3620300214 1:CAS:528:DyaK3cXitlSrtb4%3D (Pubitemid 20212832)
20. Haggblom MM, Bossert ID (2003) Dehalogenation: microbial processes and environmental applications, 1st edn. Springer, New York, pp 19-32
21. M Hofrichter F Bublitz W Fritsche 1994 Unspecific degradation of halogenated phenols by the soil fungus Penicillium frequentans Bi 7/2 J Basic Microbiol 34 163 172 10.1002/jobm.3620340306 1:CAS:528:DyaK2MXptlaguw%3D%3D
22. P Kampfer RM Kroppenstedt 2004 Pseudonocardia benzenivorans sp. nov Int J Syst Evol Microbiol 54 749 751 10.1099/ijs.0.02825-0 (Pubitemid 38771775)
23. BD Key RD Howell CS Criddle 1997 Fluorinated organics in the biosphere Environ Sci Technol 31 2445 2454 10.1021/es961007c 1:CAS:528:DyaK2sXks1Cqsb0%3D (Pubitemid 27382363)
24. S Mahendra L Alvarez-Cohen 2006 Kinetics of 1, 4-dioxane biodegradation by monooxygenase-expressing bacteria Environ Sci Technol 40 5435 5442 10.1021/es060714v 1:CAS:528:DC%2BD28XntFKlu70%3D (Pubitemid 44373110)
25. J Marr S Kremer O Sterner H Anke 1996 Transformation and mineralization of halophenols by Penicillium simplicissimum SK9117 Biodegradation 7 165 171 10.1007/BF00114628 1:CAS:528:DyaK28XjtlSgtLg%3D
26. AE Mars T Kasberg SR Kaschabek MH Van Agteren DB Janssen W Reineke 1997 Microbial degradation of chloroaromatics: use of the meta-cleavage pathway for mineralization of chlorobenzene J Bacteriol 179 4530 4537 1:CAS:528: DyaK2sXksFChu74%3D
27. M Nozaki 1970 Metapyrocatechase (Pseudomonas) Meth Enzymol 17A 522 525 10.1016/0076-6879(71)17235-7
28. RH Oltmanns R Muller MK Otto F Lingens 1989 Evidence for a new pathway in the bacterial degradation of 4-fluorobenzoate Appl Environ Microbiol 55 2499 2504 1:CAS:528:DyaL1MXlvFWhtr0%3D
29. BK Park NR Kitteringham PM O'Neill 2001 Metabolism of fluorine-containing drugs Annu Rev Pharmacol Toxicol 41 443 470 10.1146/annurev.pharmtox.41.1.443 1:CAS:528:DC%2BD3MXjsVaqtrc%3D (Pubitemid 32385895)
30. A Schreiber M Hellwiq E Dorn W Reineke HJ Knackmuss 1980 Critical reactions in fluorobenzoic acid degradation by Pseudomonas sp. B13 Appl Environ Microbiol 39 58 67 1:CAS:528:DyaL3cXhsVaqu7s%3D
31. DR Thakker H Yagi JM Sayer 1984 Effects of a 6-fluoro substituent on the metabolism of benzo(a)pyrene 7, 8-dihydrodiol to bay-region diol epoxides by rat liver enzymes J Biol Chem 259 11249 11256 1:CAS:528:DyaL2cXmt1Cnuro%3D
32. KH Van Pee S Unversucht 2003 Biological dehalogenation and halogenation reactions Chemosphere 52 299 312 10.1016/S0045-6535(03)00204-2 (Pubitemid 36612864)
33. MY Whalen SM Armstrong TR Patel 1993 Characterization of a Rhodococcus species that utilizes numerous aromatics Soil Biol Biochem 25 759 762 10.1016/0038-0717(93)90118-U 1:CAS:528:DyaK3sXlslOgtrg%3D
34. GM Zaitsev EG Surovtseva 2000 Growth of Rhodococcus opacus on mixtures of monohalogenated benzenes and phenols Microbiology 69 401 405 10.1007/BF02756763 1:CAS:528:DC%2BD3cXmtFClt7c%3D
35. GM Zaitsev JS Uotila IV Tsitko AG Lobanok MS Salkinoja-Salonen 1995 Utilization of halogenated benzenes, phenols, and benzoates by Rhodococcus opacus GM-14 Appl Environ Microbiol 61 4191 4201 1:CAS:528:DyaK2MXpslCmsL8%3D