Activity and reaction mechanism of the initial enzymatic step specifying the microbial degradation of 2,4-dichlorophenoxyacetate

Engineering in Life Sciences

Volumn 7, Issue 4, 2007, Pages 311-321

  Muller R H ^a  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

Author keywords

Biodegradation; Enzymes; Herbicides; Xenobiotics

Indexed keywords

DEGRADATION RATE; MICROBIAL DEGRADATION;

CATALYST REGENERATION; ENZYME ACTIVITY; ETHERS; HERBICIDES; METABOLITES; REACTION KINETICS;

BIODEGRADATION;

2 (2,4 DICHLOROPHENOXY)PROPIONATE; 2 (4 CHLORO 2 METHYLPHENOXY)ACETIC ACID; 2,4 DICHLOROPHENOXYACETIC ACID; DICHLORPROP; HERBICIDE; MECOPROP; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

BIODEGRADATION; CATALYST REGENERATION; ENZYME ACTIVITY; ETHERS; HERBICIDES; METABOLITES; REACTION KINETICS;

BIODEGRADATION; BIOMASS; CHEMICAL REACTION; ENZYME ACTIVITY; HERBICIDE; INOCULATION; MICROBIOLOGY; XENOBIOTICS;

ARTICLE; BACTERIAL STRAIN; BIOMASS; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENVIRONMENTAL MANAGEMENT; ENZYME ACTIVITY; MICROBIAL DEGRADATION; NONHUMAN; STARVATION;

BRADYRHIZOBIUM SP.; DELFTIA ACIDOVORANS;

EID: 34547464209     PISSN: 16180240     EISSN: 16182863     Source Type: Journal    
DOI: 10.1002/elsc.200720198     Document Type: Article

References (50)

1. W. Babel, R. H. Müller, Microorganisms as catalysts for the decontamination of ecosystems, in Encyclopedia of Life Support Systems, Eolss Publ., Oxford (UK) 2002, E6-58-06-06, pp 1-24. www.eolss.net
2. R. H. Müller, W. Babel, A theoretical study on the metabolic requirements resulting from α-ketoglutarate-dependent cleavage of phenoxyalkanoates, Appl. Environ. Microbiol. 2000, 66, 339-344.
3. R. H. Müller, W. Babel, Pseudo-recalcitrance of phenoxyalkanoate herbicides caused by a shortage of α-ketoglutarate, Acta Biotechnol. 2001, 21, 227-242.
4. F. Fukumori, R. P. Hausinger, Alcaligenes eutrophus JMP 134 "2,4-dichlorophenoxyacetate monooxygenase" is an α-ketoglutarate dependent dioxygenase, J. Bacteriol. 1993, 175, 2083-2086.
5. F. Fukumori, R. P. Hausinger, Purification and characterization of 2,4-dichlorophenoxyacetate/α-ketoglutarate dioxygenase, J. Biol. Chem. 1993, 268, 24311-24317.
6. E. R. Saari, D. A. Hogan, R. P. Hausinger, Stereospecific degradation of the phenoxypropionate herbicide dichlorprop, J. Mol. Catal. B: Enzymatic 1999, 6, 421-428.
7. A. Westendorf, R. H. Müller, W. Babel, Purification and characterization of the enantiospecific dioxygenases from Delftia acidovorans MC1 initiating the degradation of phenoxypropionate and phenoxyacetate herbicides, Acta Biotechnol. 2003, 23, 3-17.
8. A. Westendorf, D. Benndorf, T. Pribyl, H. Harms, R. H. Müller, Kinetic traits and enzyme form patterns of (R)-2,4-dichlorophenoxypropionate/α-ketoglutarate dioxygenase (RdpA) after expression in different bacterial strains. Eng. Life Sci. 2006, 6, 552-559.
9. K. Nickel, M. J. F. Suter, H. P. E. Kohler, Involvement of two α-ketoglutarate-dependent dioxygenases in enantioselective degradation of (R)- and (S)-mecoprop by Sphingomonas herbicidovorans MH, J. Bacteriol. 1997, 179, 6674-6679.
10. T. A. Muller, T. Fleischmann, J. R. van der Meer, H. P. Kohler, Purification and characterization of two enantioselective alpha-ketoglutarate-dependent dioxygenases, RdpA and SdpA, from Sphingomonas herbicidovorans MH, Appl. Environ. Microbiol. 2006, 72, 4853-4861.
11. H. Sträuber, R. H. Müller, W. Babel, Evidence of cytochrome P450-catalyzed cleavage of the ether bond of phenoxybutyrate herbicides in Rhodococcus erythropolis K2-3, Biodegradation 2003, 14, 41-50.
12. L. Xun, K. B. Wagnon, Purification and properties of component B of 2,4,5-trichlorophenoxyacetate oxygenase from Pseudomonas cepacia AC1100, Appl. Environ. Microbiol. 1995, 61, 3499-3502.
13. W. Kitagawa, S. Takami, K. Miyauchi, E. Masai, Y. Kamagata, J. M. Tiedje et al., Novel 2,4-dichlorophenoxyacetic acid degradation genes from oligotrophic Bradyrhizobium sp. strain HW13 isolated from a pristine environment, J. Bacteriol. 2002, 184, 509-518.
14. K. Itoh, Y. Tashiko, K. Uobe, Y. Kamagata, K. Suyama, H. Yamamoto, Root nodule Bradyrhizobium spp. harbor tfdAa and cadA, homologous with genes encoding 2,4-dichlorophenoxyacetic acid-degrading proteins, Appl. Environ. Microbiol. 2004, 70, 2110-2118.
15. K. Itoh, R. Kanda, Y. Sumita, H. Kim, Y. Kamagata, K. Suyama, et al., tfdA-like genes in 2,4-dichlorophenoxyacetic acid-degrading bacteria belonging to the Bradyrhizobium-Agromonas-Nitrobacter-Afipia cluster in a-Proteobacteria, Appl. Environ. Microbiol. 2002, 68, 3449-3454.
16. R. H. Müller, S. Kleinsteuber, W. Babel, Physiological and genetic characteristics of two bacterial strains exhibiting phenoxyacetate- and phenoxypropionate-utilizing activity, Microbiol. Res. 2001, 156, 121-131.
17. K. H. Oh, O. H. Tuovinen, Degradation of 2,4-dichlorophenoxyacetic acid by mixed cultures of bacteria, J. Ind. Microbiol. 1990, 6, 275-278.
18. A. Liu, Y. N. Ho, L. Que, Jr, Alternative reactivity of an α-ketoglutarate-dependent iron(II) dioxygenase: enzyme self-hydroxylation, J. Am. Chem. Soc. 2001, 123, 5126-5127.
19. 4) complexes, J. Am. Chem. Soc. 1995, 117, 3999-4013.
20. R. H. Don, J. M. Pemberton, Properties of six pesticide degradation plasmids isolated from Alcaligenes paraduxus and Alcaligenes eutrophus, J. Bacteriol. 1981, 145, 681-686.
21. D. H. Pieper, W. Reineke, K. H. Engesser, H. J. Knackmuss, Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid, and 2- methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134, Arch. Microbiol. 1988, 151, 365-371.
22. P. Vandamme, T. Coeyne, Taxonomy of the genus Cupriavidus: a tale of lost and found, Int. J. System. Evol. Microbiol. 2004, 54, 2285-2289.
23. T. A. Muller, S. M. Byrde, C. Werlen, J. R. van der Meer, H. P. Kohler, Genetic analysis of phenoxyalkanoic acid degradation in Sphingomonas herbicidovorans MH, Appl. Environ Microbiol. 2004, 70, 6066-6075.
24. R. H. Müller, W. Babel, Delftia acidovorans MC1 resists high herbicide concentrations: a study of nutristat growth on (RS)-2-(2,4-dichlorophenoxy)propionate and 2,4-dichlorophenoxyacetate, Biosci. Biotechnol. Biochem. 2004, 68, 622-530.
25. R. H. Müller, W. Babel, Measurement of growth at very low rates (μ ≥ 0), an approach to study the energy requirement for the survival of Alcaligenes eutrophus JMP 134, Appl. Environ. Microbiol. 1996, 62, 147-151.
26. R. Y. Morita, Bacteria in Oligotrophic Environments, Chapman and Hall, New York 1997.
27. R. Ravatn, S. Studer, D. Springael, A. J. B. Zehnder, J. R. van der Meer, Chromosomal integration, tandem amplification, and deamplification in Pseudomonas putida F1 of a 105-kilobase genetic element containing the chlorocatechol degradative genes from Pseudomonas sp. strain B13, J. Bacteriol. 1998, 180, 4360--4369.
28. M. Klemba, B. Jacobs, R. M. Wittich, D. Pieper, Chromosomal integration of tcb chlorocatechol degradation pathway genes as a means of expanding the growth substrate range of bacteria to include haloaromatics, Appl. Environ. Microbiol. 2000, 66, 3255-3261.
29. II gene modules in catabolism of 3-chlorobenzoate by Ralstonia eutropha JMP134 (pJP4), Appl. Environ. Microbiol. 2000, 66, 1602-1608.
30. C. M. Laemmli, J. H. J. Leveau, A. J. B. Zehnder, J. R. van der Meer, Characterization of a second tfd cluster for chlorophenol and chlorocatechol metabolism on plasmid pJP4 in Ralstonia eutropha JMP134 (pJP4), J. Bacteriol. 2000, 182, 4165-4172.
31. G. D. DiGiovanni, J. W. Neilson, I. L. Pepper, N. A. Sinclar, Gene transfer of Alcaligenes eutrophus JMP134 plasmid pJP4 to indigenous soil recipients, Appl. Environ. Microbiol. 1996, 62, 2521-2526.
32. E. M. Top, P. van Daele, N. de Saeyer, L. J. Forney, Enhancement of 2,4-dichlorophenoxyacetic acid (2,4-D) degradation in soil by dissemination of catabolic plasmids, Antonie van Leeuwenhoek 1998, 73, 87-94.
33. D. T. Newby, K. L. Josephson, I. L. Pepper, Detection and characterization of plasmid pJP4 transfer to indigenous soil bacteria, Appl. Environ. Microbiol. 2000, 66, 290-296.
34. E. M. Top, D. Springael, The role of mobile genetic elements in bacterial adaptation to xenobiotic compounds, Curr. Opin. Biotechnol. 2003, 14, 262-269.
35. S. Kleinsteuber, R. H. Müller, W. Babel, Expression of the 2,4-D degradative pathway of pJP4 in a moderately haloalkaliphilic soda lake isolate, Halomonas sp. EF43, Extremophiles 2001, 5, 375-384.
36. B. Kiesel, R. H. Müller, S. Kleinsteuber, Adaptive potential of alkaliphilic bacteria towards chloroaromatic substrates assessed by a gfp-tagged 2,4-D degradation plasmid, Eng. Life Sci. 2007, 4 (7), 361-372. DOI: 10.1002/elsc.200720200
37. D. Hoffmann, S. Kleinsteuber, R. H. Müller, W. Babel, Structural organization and localization of the chlorocatechol pathway in the 2,4-D degrading alkalitolerant strain Delftia acidovorans P4a, Microbiology 2003, 149, 2545-2556.
38. K. M. Schleinitz, S. Kleinsteuber, T. Vallaeys, W. Babel, The genetic background of 2,4-dichlorophenoxypropionate cleavage in Delftia acidovorans MC1, Appl. Environ. Microbiol. 2004, 70, 5357-5365.
39. G. Fielding, Leaching of phenylalkanoic acid herbicides from farmland, Sci. Total Environ. 1995, 168, 11-18.
40. R. D. Wilson, J. Geronimo, J. A. Armbruster, 2,4-D dissipation in field soils after applications of 2,4-D dimethylamine salt and 2,4-D 2-ethylhexyl ester, Environ. Toxicol. Chem. 1997, 16, 1239-1246.
41. Groundwater Quality and Quantity in Europe, environmental assessment report No. 3 (Ed.: European Environment Agency), Copenhagen (Denmark) 1999.
42. R. R. Fulthorpe, A. H. Rhodes, O.V. Maltseva, W. E. Holben, J. M. Tiedje, 2,4-dichlorophenoxyacetic acid-degrading bacteria contain mosaics of catabolic genes, App. Environ. Microbiol. 1995, 61, 3274-3281.
43. J. O. Ka, W. E. Holben, J. M. Tiedje, Genetic and phenotypic diversity of 2,4-dichlorophenoxyacetic acid (2,4-D)-degrading bacteria isolated from 2,4-D-treated field soils, Appl. Environ. Microbiol. 1994, 60, 1106-1115.
44. T. Vallaeys, L. Courde, C. McGowan, A. D. Wright, R. R. Fulthorpe, Phylogenetic analyses indicate independent recruitment of diverse gene cassettes during assemblage of the 2,4-D catabolic pathway, FEMS Microbiol. Ecol. 1999, 28, 373-382.
45. D. Hoffmann, R. H. Müller, B. Kiesel, W. Babel, Isolation and characterization of an alkaliphilic bacterium capable of growing on 2,4-dichlorophenoxyacetic acid and 4-chloro-2-methylphenoxyacetic acid, Acta Biotechnol. 1996, 16, 121-131.
46. R. R. Fulthorpe, A. N. Rhodes, J. M. Tiedje, Pristine soils mineralize 3-chlorobenzoate and 2,4-dichlorophenoxyacetate via different microbial populations, Appl. Environ. Microbiol. 1996, 62, 1159-1166.
47. N. Tuxen, J. R. de Lipthay, H. J. Albrechtsen, J. Aamand, P. L. Bjerg, Effect of exposure history on microbial herbicide degradation in an aerobic aquifer affected by a point source, Environ. Sci. Technol. 2002, 36, 2205-2212.
48. J. R. de Lipthay, N. Tuxen, K. Johnsen, L. H. Hansen, H. J. Albrechtsen, P. L. Bjerg et al., In situ exposure to low herbicide concentrations affects microbial population composition and catabolic gene frequency in an aerobic shallow aquifer, Appl. Environ. Microbiol. 2003, 69, 461-467.
49. H. J. Albrechtsen, M. S. Mills, J. Aamand, P. L. Bjerg, Degradation of herbicides in shallow Danish aquifers: an integrated laboratory and field study, Pest Manag. Sci. 2001, 57, 341-350.
50. L. Torang, N. Nyholm, H. J. Albrechtsen, Shifts in biodegradation of the herbicides MCPP and 2,4-D at low concentrations in aerobic aquifer materials, Environ. Sci. Technol. 2003, 37, 3095-3103.