1887

Abstract

Summary: We have examined the degradation of C ring- and side-chain-labelled 2,4,5-trichlorophenoxyacetic acid by and The effects of Mn on the degradation of these radiolabeled substrates by D. squalens and the effect of nitrogen limitation on their degradation by suggested that in both fungi, side-chain cleavage was catalysed by a mechanism independent of the lignin degradation system, whereas the degradation of the aromatic ring was dependent on the lignin degradative system. Using unlabelled substrates, a pathway for the degradation of chlorophenoxyacetic acids was elucidated in Time courses for the degradation of unlabelled chlorophenoxyacetic acids by demonstrated that the corresponding chlorophenol was the initial product formed. The chlorophenol intermediate was xylosylated to form the chlorophenolxyloside. In turn, the chlorophenolxyloside could be hydrolysed by an intracellular -xylosidase to regenerate the chlorophenol. The chlorophenol product of the xylosidase reaction was oxidatively dechlorinated to form 2-chloro--benzoquinone which could undergo subsequent further dechlorination and ring-opening reactions, as has been reported previously for

Funding
This study was supported by the:
  • US Environmental Protection Agency (Award R-821269-01)
  • US Department of Energy, Division of Energy Biosciences (Award DE-FG03-96ER20235 and DE-FG06-92ER20093)
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1997-07-01
2021-04-21
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References

  1. Alic M., Letzring C., Gold M. H. 1987; Mating system and basidiospore formation in the lignin-degrading basidiomycete Phanerochaete chrysosporium . Appl Environ Microbiol 53:1464–1469
    [Google Scholar]
  2. Brock B. J., Gold M. H. 1996; 1,4-Benzoquinoine reductase from the basidiomycete Phanerochaete chrysosporium: spectral and kinetic analysis. Arch Biochem Biophys 331:31–40
    [Google Scholar]
  3. Brock B. J., Rieble S., Gold M. H. 1995; Purification and characterization of a 1,4-benzoquinone reductase from the basidiomycete Phanerochaete chrysosporium . Appl Environ Microbiol 61:3076–3081
    [Google Scholar]
  4. Bumpus J. A., Aust S. D. 1987; Biodegradation of environmental pollutants by the white rot fungus Phanerochaete chrysosporium: involvement of the lignin-degrading system. Bioessays 6:166–170
    [Google Scholar]
  5. Buswell J. A., Odier E. 1987; Lignin biodegradation. Crit Rev Biotechnol 6:1–60
    [Google Scholar]
  6. Chaplin M. F. 1986 Monosaccharides. . In Carbohydrate Analysis. A Practical Approach , pp. 1–36 . Edited by Chaplin M. F., Kennedy J. F. Washington, DC: IRL Press;
    [Google Scholar]
  7. Elo H. A., Hervonen H., Ylitalo P. 1988; Comparative study on cerebrovascular injuries by three chlorophenoxyacetic acids (2,4-D, 2,4,5-T and MCPA). Comp Biochem Physiol C 90:65–68
    [Google Scholar]
  8. Eriksson K.-E. L.,, Blanchette R. A., Ander P. 1990 Biodegradation of lignin. . In Microbial and Enzymatic Degradation of Wood and Wood Components , pp. 225–333 . Edited by Timell T. E. Berlin: Springer-Verlag;
    [Google Scholar]
  9. Fukumori F., Hausinger R. P. 1993; Purification and characterization of 2,4-dichlorophenoxyacetate/α-ketoglutarate dioxygenase. J Biol Chem 268:24311–24317
    [Google Scholar]
  10. Furniss B. S., Hannaford A. J., Smith P. W. G., Tatchell A. R. (revisors) 1989 . Chapter 6 Aromatic compounds. . In Vogel’s Textbook of Practical Organic Chemistry , 5th edn Essex, UK: Longman Scientific & Technical;
    [Google Scholar]
  11. Gold M. H., Alic M. A. 1993; Molecular biology of the lignin-degrading basidiomycete Phanerochaete chrysosporium . Microbiol Rev 57:605–622
    [Google Scholar]
  12. Grant W. F. 1979; The genotoxic effects of 2,4,5-T. Mutat Res 65:83–119
    [Google Scholar]
  13. Hammel K. E. 1989; Organopollutant degradation by ligninolytic fungi. Enzyme Microb Technol 11:776–777
    [Google Scholar]
  14. Hatakka A. 1990; Lignin-modifying enzymes from selected white-rot fungi: production and role in lignin degradation. FEMS Microbiol Rev 13:125–135
    [Google Scholar]
  15. Haugland R. A., Schlemm D. J., Lyons R. P., Ill, Sferra P. R., Chakrabarty A. M. 1990; Degradation of the chlorinated phenoxyacetate herbicides 2,4-dichlorophenoxyacetic acid and 2,4,5-trichlorophenoxyacetic acid by pure and mixed bacterial cultures. Appl Environ Microbiol 56:1357–1362
    [Google Scholar]
  16. Higuchi T. 1990; Lignin biochemistry: biosynthesis and biodegradation. Wood Sci Technol 24:23–63
    [Google Scholar]
  17. Hileman B. 1996; Immune system suppression linked to widely used pesticides. Chem Eng News 74:23
    [Google Scholar]
  18. Joshi D. K., Gold M. H. 1993; Degradation of 2,4,5-trichlorophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium . Appl Environ Microbiol 59:1779–1785
    [Google Scholar]
  19. Kilbane J. J., Chatterjee D. K., Karns J. S., Kellogg S. T., Chakrabarty A. M. 1982; Biodegradation of 2,4,5-trichlorophenoxyacetic acid by a pure culture of Pseudomonas cepacia . Appl Environ Microbiol 44:72–78
    [Google Scholar]
  20. Kirk T. K., Farrell R. L. 1987; Enzymatic ‘combustionO’: the microbial degradation of lignin. Annu Rev Micribiol 41:465–505
    [Google Scholar]
  21. Kirk T. K., Schultz E., Connors W. J., Lorenz L. F., Zeikus J. G. 1978; Influence of culture parameters on lignin metabolism by Phanerochaete chrysosporium . Arch Microbiol 117:277–285
    [Google Scholar]
  22. Kondo R., Yamagami H., Sakai K. 1993; Xylosylation of phenolic hydroxyl group of lignin model compounds by Coriolus versicolor . Appl Environ Microbiol 59:438–441
    [Google Scholar]
  23. Lamar R.T., Dietrich D.M. 1990; In situ depletion of pentachlorophenol from contaminated soil by Phanerochaete spp. Appl Environ Microbiol 56:3093–3100
    [Google Scholar]
  24. Loos M. A. 1975 Phenoxyalkanoic acids. . In Herbicides: Chemistry, Degradation, and Mode of Action , vol. 1 , pp. 1–128 . Edited by Kearney P. C., Kaufman D. D. New York: Marcel Dekker;
    [Google Scholar]
  25. McCall P. J., Vrona S. A., Kelley S. S. 1981; Fate of uniformly carbon-14 ring-labeled 2,4,5-trichlorophenoxyacetic acid and 2,4-dichlorophenoxyacetic acid. J Agric Food Chem 29:100–107
    [Google Scholar]
  26. Mulder G. J. 1982 Conjugation of phenols. . In Metabolic Basis of Detoxication: Metabolism of Functional Groups , chapter 13, pp. 247–269 Edited by Jakoby B., Bend J. R., Caldwell J. New York: Academic Press;
    [Google Scholar]
  27. Oliveira G. H., Palermo-Neto J. 1993; Effects of 2,4-dichlorophenoxyacetic acid (2,4-D) on open-field behavior and neurochemical parameters of rats. Pharmacol Toxicol 73:79–85
    [Google Scholar]
  28. Périé F. H., Gold M. H. 1991; Manganese regulation of manganese peroxidase expression and lignin degradation by the white-rot fungus Dichomitus squalens . Appl Environ Microbiol 57:2240–2245
    [Google Scholar]
  29. Périé F. H., Sheng D., Gold M. H. 1996; Purification and characterization of two manganese peroxidase isozymes from the white-rot basidiomycete Dichomitus squalens . Biochim Biophys Acta 1297:139–148
    [Google Scholar]
  30. Pieper D. H., Reineke W., Engesser K.-H., Knackmuss H.-J. 1988; Metabolism of 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid and 2-methylphenoxyacetic acid by Alcaligenes eutrophus JMP 134. Arch Microbiol 150:95–102
    [Google Scholar]
  31. Rieble S., Joshi D. K., Gold M. H. 1994; Purification and characterization of a 1,2,4-trihydroxybenzene-1,2-dioxygenase from the basidiomycete Phanerochaete chrysosporium . J Bacteriol 176:4838–4844
    [Google Scholar]
  32. Ryan T. P., Bumpus J. A. 1989; Biodegradation of 2,4,5-trichlorophenoxyacetic acid in liquid culture and in soil by the white rot fungus Phanerochaete chrysosporium . Appl Microbiol Biotechnol 31:302–307
    [Google Scholar]
  33. Sinton G. L., Fan L. T., Erickson L. E., Lee S. M. 1986; Biodegradation of 2,4-D and related xenobiotic compounds. Enzyme Microb Technol 8:395–403
    [Google Scholar]
  34. Sutherland J. B., Selby A. L., Freeman J. P., Evans F. E., Cerniglia C. E. 1991; Metabolism of phenanthrene by Phanerochaete chrysosporium . Appl Environ Microbiol 57:3310–3316
    [Google Scholar]
  35. Valli K., Gold M. H. 1991; Degradation of 2,4-dichlorophenol by the lignin-degrading fungus Phanerochaete chrysosporium . J Bacteriol 73:345–352
    [Google Scholar]
  36. Valli K., Wariishi H., Gold M. H. 1992; Degradation of 2,7-dichlorodibenzo-p-dioxin by the lignin-degrading basidiomycete Phanerochaete chrysosporium . J Bacteriol 174:2131–2137
    [Google Scholar]
  37. Yadav J. S., Reddy C. A. 1992; Non-involvement of lignin peroxidases and manganese peroxidases in 2,4,5-trichlorophenoxyacetic acid degradation by Phanerochaete chrysosporium . Biotechnol Lett 14:1089–1092
    [Google Scholar]
  38. Yadav J. S., Reddy C. A. 1993; Mineralization of 2,4-dichlorophenoxyacetic acid (2,4-D) and mixtures of 2,4-D and 2,4,5-trichlorophenoxyacetic acid by Phanerochaete chrysosporium . Appl Environ Microbiol 59:2904–2908
    [Google Scholar]
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