Chlorophenol hydroxylases encoded by plasmid pJP4 differentially contribute to chlorophenoxyacetic acid degradation

Applied and Environmental Microbiology

Volumn 72, Issue 4, 2006, Pages 2783-2792

  Ledger, T ^a   Pieper, D H ^b   Gonzalez B ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; DEGRADATION; GENES; HYDROLYSIS; PHENOLS; TOXICITY;

BURKHOLDERIA XENOVORANS; CHLOROCATECHOLS; CHLOROPHENOXYACETATE DEGRADATION; PHENOXYACETIC ACID DEGRADATION;

ENZYMES;

2,4 DICHLOROPHENOL; 4 CHLORO ORTHO CRESOL; AROMATIC COMPOUND; CHLOROPHENOL; CHLOROPHENOXYACETIC ACID; HERBICIDE; OXYGENASE; PHENOL DERIVATIVE; PHENOXYACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

DEGRADATION; ENZYME; ENZYME ACTIVITY; GENE; HERBICIDE; PLASMID;

ARTICLE; BACTERIAL GENE; BACTERIAL GROWTH; BACTERIUM MUTANT; BIODEGRADATION; ENZYME ASSAY; ESCHERICHIA COLI; GENE INACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PLASMID; POLLUTANT; TFDB GENE; TOXICITY TESTING;

2,4-DICHLOROPHENOXYACETIC ACID; 2-METHYL-4-CHLOROPHENOXYACETIC ACID; BACTERIAL PROTEINS; BIODEGRADATION, ENVIRONMENTAL; BURKHOLDERIACEAE; CHLOROPHENOLS; HERBICIDES; MIXED FUNCTION OXYGENASES; PLASMIDS; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS); BURKHOLDERIA XENOVORANS; CUPRIAVIDUS NECATOR; ESCHERICHIA COLI;

EID: 33646102690     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.72.4.2783-2792.2006     Document Type: Article

References (38)

1. Ausubel, F., R. Brent, R. Kingston, D. Moore, J. Seidman, J. Smith, and K. Struhl (ed.). 1992. Short protocols in molecular biology, 2nd ed. Greene Publishing Associates, New York, N.Y.
2. Beadle, C. A., and A. R. W. Smith. 1982. The purification and properties of 2,4-dichlorophenol hydroxylase from a strain of Acinetobacter species. Eur. J. Biochem. 123:323-332.
3. Clément, P., V. Matus, L. Cárdenas, and B. González. 1995. Degradation of trichlorophenols by Alcaligenes eutrophus JMP134. FEMS Microbiol. Lett. 127:51-55.
4. Datsenko, K. A., and B. L. Wanner. 2000. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc. Natl. Acad. Sci. USA 97:6640-6645.
5. Don, R. H., and J. M. Pemberton. 1981. Properties of six pesticide degradation plasmids isolated from Alcaligenes paradoxus and Alcaligenes eutrophus, J. Bacteriol. 145:681-686.
6. Farhana, L., and P. B. New. 1997. The 2,4-dichlorophenol hydroxylase of Alcaligenes eutrophus JMP134 is a homotetramer. Can. J. Microbiol. 43:202-205.
7. Fritsche, K., G. Auling, J. R. Andreesen, and U. Lechner. 1999. Defluvibacter lusatiae gen. nov., sp. nov., a new chlorophenol-degrading member of the alpha-2 subgroup of proteobacteria. Syst. Appl. Microbiol. 22:197-204.
8. Fukumori, F., and R. P. Hausinger. 1993. Alcaligenes eutrophus JMP134 "2,4-dichlorophenoxyacetate monooxygenase" is an α- ketoglutarate-dependent dioxygenase. J. Bacteriol. 175:2083-2086.
9. Gerischer, U., and L. N. Ornston. 1995. Spontaneous mutations in pcaH and -G, structural genes for protocatechuate 3,4-dioxygenase in Acinetobacter calcoaceticus. J. Bacteriol. 177:1336-1347.
10. Gobel, M., K. Kassel-Cati, E. Schmidt, and W. Reineke. 2002. Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: cloning, characterization, and analysis of sequences encoding 3-oxoadipate:succinyl- coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase. J. Bacteriol. 184:216-223.
11. Herrero, M., V. de Lorenzo, and K. N. Timmis. 1990. Transposon vectors containing non-antibiotic selection markers for cloning and stable chromosomal insertion of foreign DNA in gram-negative bacteria. J. Bacteriol. 172:6557-6567.
12. Hoffmann, D., S. Kleinsteuber, R. H. Muller, and W. Babel. 2003. A transposon encoding the complete 2,4-dichlorophenoxyacetic acid degradation pathway in the alkalitolerant strain Delftia acidovorans P4a. Microbiology 149:2545-2556.
13. Jeong, J. J., J. H. Kim, C. K. Kim, I. Hwang, and K. Lee. 2003. 3- and 4-alkylphenol degradation pathway in Pseudomonas sp. strain KL28: genetic organization of the lap gene cluster and substrate specificities of phenol hydroxylase and catechol 2,3-dioxygenase. Microbiology 149:3265-3277.
14. Kivisaar, M., R. Horak, L. Kasak, A. Heinaru, and J. Habicht. 1990. Selection of independent plasmids determining phenol degradation in Pseudomonas putida and the cloning and expression of genes encoding phenol mono-oxygenase and catechol 1,2-dioxygenase. Plasmid 24:25-36.
15. Koh, S. C., M. V. McCullar, and D. D. Focht. 1997. Biodegradation of 2,4-dichlorophenol through a distal meta-fission pathway. Appl. Environ. Microbiol. 58:1276-1283.
16. Kovach, M. E., R. W. Phillips, P. H. Elzer, R. M. Roop II, and K. M. Peterson. 1994. pBBR1MCS: a broad-host-range cloning vector. BioTechniques 16:800-802.
17. Kröckel, L., and D. D. Focht. 1987. Construction of chlorobenzene-utilizing recombinants by progenitive manifestation of a rare event. Appl. Environ. Microbiol. 53:2470-2475.
18. Laemmli, C. M., J. H. Leveau, A. J. B. Zehnder, and J. R. van der Meer. 2000. Characterization of a second tfd gene cluster for chlorophenol and chlorocatechol metabolism on plasmid pJP4 in Ralstonia eutropha JMP134 (pJP4). J. Bacteriol. 182:4165-4172.
19. Laemmli, C. M., C. Werlen, and J. R. van der Meer. 2004. Mutation analysis of the different tfd genes for degradation of chloroaromatic compounds in Ralstonia eutropha JMP134. Arch. Microbiol. 181:112-121.
20. Lefebre, M. D., and M. Valvano. 2002. Construction and evaluation of plasmid vectors optimized for constitutive and regulated gene expression in Burkholderia cepacia complex isolates. Appl. Environ. Microbiol. 68:5956-5964.
21. Leveau, J. H., A. J. B. Zehnder, and J. R. van der Meer. 1998. The tfdK gene product facilitates uptake of 2,4-dichlorophenoxyacetate by Ralstonia eutropha JMP134 (pJP4). J. Bacteriol. 180:2237-2243.
22. Leveau, J. H., F. Konig, H. Fuchslin, C. Werlen, and J. R. van der Meer. 1999. Dynamics of multigene expression during catabolic adaptation of Ralstonia eutropha JMP134 (pJP4) to the herbicide 2,4-dichlorophenoxyacetate. Mol. Microbiol. 33:396-406.
23. Liu, T., and P. J. Chapman. 1984. Purification and properties of a plasmid-encoded 2,4-dichlorophenol hydroxylase. FEBS Lett. 173:314-318.
24. Makdessi, K., and U. Lechner. 1997. Purification and characterization of 2,4-dichlorophenol hydroxylase isolated from a bacterium of the alpha-2 subgroup of the Proteobacteria. FEMS Microbiol. Lett. 157:95-101.
25. Nurk, A., L. Kasak, and M. Kivisaar. 1991. Sequence of the gene (pheA) encoding phenol monooxygenase from Pseudomonas sp. EST1001: expression in Escherichia coli and Pseudomonas putida. Gene 102:13-18.
26. Parke, D., and L. N. Ornston. 2004. Toxicity caused by hydroxycinnamoyl-coenzyme A thioester accumulation in mutants of Acinetobacter sp. strain ADP1. Appl. Environ. Microbiol. 70:2974-2983.
27. II gene modules in catabolism of 3-chlorobenzoatc by Ralstonia eutropha JMP134 (pJP4). Appl. Environ. Microbiol. 66:1602-1608.
28. Pérez-Pantoja, D., T. Ledger, D. H. Pieper, and B. González. 2003. Efficient turnover of chlorocatechols is essential for growth of Ralstonia eutropha JMP134 (pJP4) in 3-chlorobenzoic acid. J. Bacteriol. 185:1534-1542.
29. Pieper, D. H., W. Reineke, K. H. Engesser, and H.-J. Knackmuss. 1988. Metabolism of 2,4-dichlorophcnoxyacetic acid, 4-chloro-2-methylphenoxy-acetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP134. Arch. Microbiol. 150:95-102.
30. Plumeier, I., D. Pérez-Pantoja, S. Heim, B. González, and D. H. Pieper. 2002. The importance of different tfd genes for the degradation of chloroaromatics by Ralstonia eutropha JMP134. J. Bacteriol. 184:4054-4064.
31. Radjendirane, V., M. A. Bhat, and C. S. Vaidyanathan. 1991. Affinity purification and characterization of 2,4-dichlorophenol hydroxylase from Pseudomonas cepacia. Arch. Biochem. Biophys. 288:169-176.
32. Schlömann, M., E. Schmidt, and H.-J. Knackmuss. 1990. Different types of dienelactone hydrolase in 4-fluorobenzoate-utilizing bacteria. J. Bacteriol. 172:5112-5118.
33. Schüürmann, G., H. Segner, and K. Jung. 1997. Multivariate mode of action analysis of acute toxicity of phenols. Aquat. Toxicol. 38:277-296.
34. Schweigert, N., A. J. B. Zehnder, and R. I. L. Eggen. 2001. Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Environ. Microbiol. 3:81-91.
35. Sikkema, J., J. A. M. de Bont, and B. Poolman. 1995. Mechanisms of membrane toxicity of hydrocarbons. Microbiol. Rev. 59:201-222.
36. Takemori, S., M. Kakamura, K. Suzuki, and M. Katagiri. 1970. The kinetics of salicylate hydroxylase reaction. FEBS Lett. 6:305-308.
37. Trefault, N., R. De la Iglesia, A. M. Molina, M. Manzano, T. Ledger, D. Pérez-Pantoja, M. A. Sánchez, M. Stuardo, and B. González. 2004. Genetic organization of the catabolic plasmid pJP4 from Ralstonia eutropha JMP134 (pJP4) reveals mechanisms of adaptation to chloroaromatic pollutants and evolution of specialized chloroaromatic degradation pathways. Environ. Microbiol. 6:655-668.
38. Vallaeys, T., L. Courde, C. McGowan, A. D. Wright, and R. R. Fulthorpe. 1999. Phylogenetic analyses indicate independent recruitment of diverse gene cassettes during assemblage of the 2.4-D catabolic pathway. FEMS Microbiol. Ecol. 28:373-382.