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. 1993 Jun;59(6):1779–1785. doi: 10.1128/aem.59.6.1779-1785.1993

Degradation of 2,4,5-trichlorophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium.

D K Joshi 1, M H Gold 1
PMCID: PMC182161  PMID: 8328802

Abstract

Under secondary metabolic conditions the white rot basidiomycete Phanerochaete chrysosporium rapidly mineralizes 2,4,5-trichlorophenol. The pathway for degradation of 2,4,5-trichlorophenol was elucidated by the characterization of fungal metabolites and oxidation products generated by purified lignin peroxidase (LiP) and manganese peroxidase (MnP). The multistep pathway involves cycles of peroxidase-catalyzed oxidative dechlorination reactions followed by quinone reduction reactions to yield the key intermediate 1,2,4,5-tetrahydroxybenzene, which is presumably ring cleaved. In the first step of the pathway, 2,4,5-trichlorophenol is oxidized to 2,5-dichloro-1,4-benzoquinone by either MnP or Lip. 2,5-Dichloro-1,4-benzoquinone is then reduced to 2,5-dichloro-1,4-hydroquinone. The 2,5-dichloro-1,4-hydroquinone is oxidized by MnP to generate 5-chloro-4-hydroxy-1,2-benzoquinone. The orthoquinone is in turn reduced to 5-chloro-1,2,4-trihydroxybenzene. Finally, the 5-chlorotrihydroxybenzene undergoes another cycle of oxidative dechlorination and reduction reactions to generate 1,2,4,5-tetrahydroxybenzene. The latter is presumably ring cleaved, with subsequent degradation to CO2. In this pathway, the substrate is oxidatively dechlorinated by LiP or MnP in a reaction which produces a quinone. The quinone intermediate is recycled by a reduction reaction to regenerate an intermediate which is again a substrate for peroxidase-catalyzed oxidative dechlorination. This pathway apparently results in the removal of all three chlorine atoms before ring cleavage occurs.

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Selected References

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  1. Alic M., Letzring C., Gold M. H. Mating System and Basidiospore Formation in the Lignin-Degrading Basidiomycete Phanerochaete chrysosporium. Appl Environ Microbiol. 1987 Jul;53(7):1464–1469. doi: 10.1128/aem.53.7.1464-1469.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Boominathan K., Dass S. B., Randall T. A., Kelley R. L., Reddy C. A. Lignin peroxidase-negative mutant of the white-rot basidiomycete Phanerochaete chrysosporium. J Bacteriol. 1990 Jan;172(1):260–265. doi: 10.1128/jb.172.1.260-265.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Glenn J. K., Gold M. H. Purification and characterization of an extracellular Mn(II)-dependent peroxidase from the lignin-degrading basidiomycete, Phanerochaete chrysosporium. Arch Biochem Biophys. 1985 Nov 1;242(2):329–341. doi: 10.1016/0003-9861(85)90217-6. [DOI] [PubMed] [Google Scholar]
  4. Gold M. H., Kuwahara M., Chiu A. A., Glenn J. K. Purification and characterization of an extracellular H2O2-requiring diarylpropane oxygenase from the white rot basidiomycete, Phanerochaete chrysosporium. Arch Biochem Biophys. 1984 Nov 1;234(2):353–362. doi: 10.1016/0003-9861(84)90280-7. [DOI] [PubMed] [Google Scholar]
  5. Kirk T. K., Farrell R. L. Enzymatic "combustion": the microbial degradation of lignin. Annu Rev Microbiol. 1987;41:465–505. doi: 10.1146/annurev.mi.41.100187.002341. [DOI] [PubMed] [Google Scholar]
  6. Lamar R. T., Larsen M. J., Kirk T. K. Sensitivity to and Degradation of Pentachlorophenol by Phanerochaete spp. Appl Environ Microbiol. 1990 Nov;56(11):3519–3526. doi: 10.1128/aem.56.11.3519-3526.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Mileski G. J., Bumpus J. A., Jurek M. A., Aust S. D. Biodegradation of pentachlorophenol by the white rot fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1988 Dec;54(12):2885–2889. doi: 10.1128/aem.54.12.2885-2889.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Reineke W., Knackmuss H. J. Microbial degradation of haloaromatics. Annu Rev Microbiol. 1988;42:263–287. doi: 10.1146/annurev.mi.42.100188.001403. [DOI] [PubMed] [Google Scholar]
  9. Spadaro J. T., Gold M. H., Renganathan V. Degradation of azo dyes by the lignin-degrading fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1992 Aug;58(8):2397–2401. doi: 10.1128/aem.58.8.2397-2401.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Valli K., Brock B. J., Joshi D. K., Gold M. H. Degradation of 2,4-dinitrotoluene by the lignin-degrading fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1992 Jan;58(1):221–228. doi: 10.1128/aem.58.1.221-228.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Valli K., Gold M. H. Degradation of 2,4-dichlorophenol by the lignin-degrading fungus Phanerochaete chrysosporium. J Bacteriol. 1991 Jan;173(1):345–352. doi: 10.1128/jb.173.1.345-352.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Valli K., Wariishi H., Gold M. H. Degradation of 2,7-dichlorodibenzo-p-dioxin by the lignin-degrading basidiomycete Phanerochaete chrysosporium. J Bacteriol. 1992 Apr;174(7):2131–2137. doi: 10.1128/jb.174.7.2131-2137.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Wariishi H., Dunford H. B., MacDonald I. D., Gold M. H. Manganese peroxidase from the lignin-degrading basidiomycete Phanerochaete chrysosporium. Transient state kinetics and reaction mechanism. J Biol Chem. 1989 Feb 25;264(6):3335–3340. [PubMed] [Google Scholar]
  14. Wariishi H., Gold M. H. Lignin peroxidase compound III. Mechanism of formation and decomposition. J Biol Chem. 1990 Feb 5;265(4):2070–2077. [PubMed] [Google Scholar]
  15. Wariishi H., Valli K., Gold M. H. In vitro depolymerization of lignin by manganese peroxidase of Phanerochaete chrysosporium. Biochem Biophys Res Commun. 1991 Apr 15;176(1):269–275. doi: 10.1016/0006-291x(91)90919-x. [DOI] [PubMed] [Google Scholar]

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