Abstract
Purified laccase from Coriolopsis gallica UAMH8260 oxidized carbazole, N-ethylcarbazole, fluorene, and dibenzothiophene in the presence of 1-hydroxybenzotriazole and 2,2′-azinobis (3-ethylbenzthiazoline-6-sulfonic acid) as free radical mediators. Susceptibility to laccase oxidation appears related to the ionization potential (IP) of the substrate: compounds with an IP above 8.52, dibenzofuran (IP = 8.77) and benzothiophene (IP = 8.73) were not attacked. Carbazole (IP = 7.68) was the most sensitive to oxidation with >99% transformed with 10 milliunits of laccase after 1 h, though most reactions were carried out for 18 h. 9-Fluorenone was identified as the product of fluorene (IP = 8.52) oxidation, and dibenzothiophene sulfone from dibenzothiophene (IP = 8.44). Although carbazole and N-ethylcarbazole were both completely removed within 18 h, no oxidation or condensation metabolites were detected. This investigation is the first to report the oxidation of dibenzothiophene, carbazole, and N-ethylcarbazole by laccase.
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References
Ambrose JF, Carpenter LL, Nelson RF (1975) Electrochemical and spectroscopic properties of cation radicals. J Electrochem. Soc. 122: 876–894.
Arjmand M, Sandermann H (1985) Mineralization of chloraniline/ lignin conjugates and of free chloranilines by white rot fungus Phanerochaete chrysosporium. J. Agric. Food Chem. 33: 1055–1060.
Beaudette LA, Davies S, Fedorak PM, Ward OP, Pickard MA (1998) Comparison of biodegradation and mineralization as methods for measuring loss of selected polychlorinated biphenyl congeners in cultures of four white rot fungi. Appl. Environ. Microbiol. 64: 2020–2025.
Beaudette LA, Ward OP, Pickard MA, Fedorak PM (2000) Low surfactant concentration increases fungal mineralization of a PCB congener but has no effect on overall oxidation. Lett. Appl. Microbiol. 30: 155–160
Bogan BW, Lamar RT (1996) Polycyclic aromatic hydrocarbondegradation capabilities of Phanerochaete leavis HHB-1625 and its extracellular ligninolytic enzymes. Appl. Environ. Microbiol. 62: 1597–1603.
Bressler DC, Fedorak PM (2000) Bacterial oxidation of fluorene, dibenzofuran, dibenzothiophene and carbazole. Can. J. Microbiol, in press.
Gianfreda L, Xu F, Bollag J-M (1999) Laccases: a useful group of oxidoreductive enzymes. Bioremediation J. 3: 1–25.
Gorontzy T, Drzyga O, Kahl MW, Bruns-Nagel D, Breitung J, von Loew E, Blotevogel KH (1994) Microbial degradation of explosives and related compounds. Crit. Rev. Microbiol. 20: 265–284.
Kersten PJ, Kalyanaraman B, Hammel KE, Reinhammar B (1990) Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes. Biochem. J. 268: 475–480.
Kirby N, McMullan G, Marchant R (1995) Decolourisation of an artificial textile effuent by Phanerochaete chrysosporium. Biotechnol. Lett. 178: 761–764.
Kullman SW, Matsumura F (1996) Metabolic pathways utilized by Phanerochaete chrysosporium for degradation of cyclodiene pesticide, Endosulfan. Appl. Environ. Microbiol. 62: 593–600.
Levin RD, Lias SG (1982) Ionization Potential and Appearance Potential Measurements, 1971–1981. U.S. Department of Commerce/ National Bureau of Standards. Ion Kinetics and Energetics Data Center, National Measurement Laboratory, National Bureau of Standards, Washington D.C.
Majcherczyk A, Johannes C, Hutterman A (1998) Oxidation of polycyclic aromatic hydrocarbons (PAH) by laccase of Trametes versicolor. Enzyme Microbiol. Tech. 22: 335–341.
Pickard MA, Roman R, Tinoco R, Vazquez-Duhalt R (1999) Polycyclic aromatic hydrocarbon oxidation by white rot fungi, and oxidation by Coriolopsis gallica UAMH 8260 laccase. Appl. Environ. Microbiol. 65: 3805–3809
Reyes P, Pickard MA, Vazquez-Duhalt R (1999) Hydroxybenzotriazole increases the range of textile dyes decolorized by immobilized laccase. Biotechnol. Lett. 21: 875–880.
Rodríguez E, Pickard MA, Vazquez-Duhalt R (1999) Industrial dye decolorization by laccases from lignolytic fungi. Curr. Microbiol. 38: 27–32.
Ruckenstein E, Wang X-B (1994) Production of lignin peroxidase by Phanerochaete chrysosporium immobilized on porous poly(styrene-divinylbenzene) carrier and its application to the degrading of 2-chlorophenol. Biotechnol. Bioeng. 44: 79–86.
Sasek V, Volfova O, Erbanova P, Vyas BRM, Matucha M (1993) Degradation of PCBs by white rot fungi, methylotrophic and hydrocarbon utilizing yeasts and bacteria. Biotechnol. Lett. 15: 521–526.
Shin KS, Oh IK, Kim CJ (1997) Production and purification of Remazol Brilliant Blue R decolorization peroxidase from the culture filtrate of Pleurotus ostreatus. Appl. Environ. Microbiol. 63: 1744–1748.
Takada S, Naksamura M, Matsueda T, Kondo R, Sakai K (1996) Degradation of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans by the white rot fungus Phanerochaete sordida YK-624. Appl. Environ. Microbiol. 62: 4323–4328.
Vignier V, Berthou F, Picart D (1983) Influence of injection systems on the gas chromatographic analysis of oxygenated dibenzothiophene. J. High Resolut. Chromatogr. Chromatr. Commun. 6: 661–665.
Woolfenden BS, Wilson RL (1982) Radical cations as reference chromogens in studies of one-electron transfer reactions: pulse radiolysis studies of 2,20-azinobis-(3-ethylbenzthiazoline-6-sulfonate). J. Chem. Soc. Perkin Trans. II, 805–812.
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Bressler, D.C., Fedorak, P.M. & Pickard, M.A. Oxidation of carbazole, N-ethylcarbazole, fluorene, and dibenzothiophene by the laccase of Coriolopsis gallica. Biotechnology Letters 22, 1119–1125 (2000). https://doi.org/10.1023/A:1005633212866
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DOI: https://doi.org/10.1023/A:1005633212866