Lignin Peroxidase Oxidation of Aromatic Compounds in Systems Containing Organic Solvents

Lignin peroxidase from Phanerochaete chrysosporium was used to study the oxidation of aromatic compounds, including polycyclic aromatic hydrocarbons and heterocyclic compounds, that are models of moieties of asphaltene molecules. The oxidations were done in systems containing water-miscible organic solvents, including methanol, isopropanol, N, N-dimethylformamide, acetonitrile, and tetrahydrofuran. Of the 20 aromatic compounds tested, 9 were oxidized by lignin peroxidase in the presence of hydrogen peroxide. These included anthracene, 1-, 2-, and 9-methylanthracenes, acenaphthene, fluoranthene, pyrene, carbazole, and dibenzothiophene. Of the compounds studied, lignin peroxidase was able to oxidize those with ionization potentials of <8 eV (measured by electron impact). The reaction products contain hydroxyl and keto groups. In one case, carbon-carbon bond cleavage, yielding anthraquinone from 9-methylanthracene, was detected. Kinetic constants and stability characteristics of lignin peroxidase were determined by using pyrene as the substrate in systems containing different amounts of organic solvent. Benzyl alkylation of lignin peroxidase improved its activity in a system containing water-miscible organic solvent but did not increase its resistance to inactivation at high solvent concentrations.

[1]  M. Tien,et al.  Oxidation of persistent environmental pollutants by a white rot fungus. , 1985, Science.

[2]  H. Wariishi,et al.  Reactions of lignin peroxidase compounds I and II with veratryl alcohol. Transient-state kinetic characterization. , 1991, The Journal of biological chemistry.

[3]  P. Brignac,et al.  The oxidation of phenol and its reaction product by horseradish peroxidase and hydrogen peroxide. , 1973, Archives of biochemistry and biophysics.

[4]  K. Hammel Organopollutant degradation by ligninolytic fungi , 1989 .

[5]  S. Onodera,et al.  Chemical changes of organic compounds in chlorinated water. XVI. Gas chromatographic-mass spectrometric studies of reactions of tricyclic aromatic hydrocarbons with hypochlorite in dilute aqueous solution. , 1989, Journal of chromatography.

[6]  R. Foster Absorption Spectra of Molecular Complexes , 1958, Nature.

[7]  E. M. Lown,et al.  The molecular structure of asphaltene: an unfolding story , 1992 .

[8]  M. Tien,et al.  Ligninolysis by a purified lignin peroxidase. , 1993, The Journal of biological chemistry.

[9]  S. Lias,et al.  Ionization Potential and Appearance Potential Measurements, 1971-1981, , 1982 .

[10]  H. Wariishi,et al.  Manganese peroxidase from the lignin-degrading basidiomycete Phanerochaete chrysosporium. Transient state kinetics and reaction mechanism. , 1989, The Journal of biological chemistry.

[11]  J A Fee,et al.  Steady-state and transient-state kinetic studies on the oxidation of 3,4-dimethoxybenzyl alcohol catalyzed by the ligninase of Phanerocheate chrysosporium Burds. , 1986, The Journal of biological chemistry.

[12]  K. Semple,et al.  Effect of water-miscible organic solvents on the catalytic activity of cytochrome c. , 1993, Enzyme and microbial technology.

[13]  C. Cerniglia,et al.  Fungal transformation of fluoranthene , 1990, Applied and environmental microbiology.

[14]  C. Cerniglia,et al.  Pyrene degradation by a Mycobacterium sp.: identification of ring oxidation and ring fission products , 1988, Applied and environmental microbiology.

[15]  M. Tien,et al.  Oxidation-reduction potentials and ionization states of extracellular peroxidases from the lignin-degrading fungus Phanerochaete chrysosporium. , 1989, Biochemistry.

[16]  K. Semple,et al.  Chloroperoxidase-mediated modifications of petroporphyrins and asphaltenes , 1993 .

[17]  M. Tien,et al.  Production of multiple ligninases by Phanerochaete chrysosporium: effect of selected growth conditions and use of a mutant strain , 1986 .

[18]  M. Leisola,et al.  Role of extracellular ligninases in biodegradation of benzo(a)pyrene by Phanerochaete chrysosporium , 1986 .

[19]  D. Westlake,et al.  Role of enzyme hydrophobicity in biocatalysis in organic solvents , 1992 .

[20]  R. Farrell,et al.  Role of Veratryl Alcohol in Regulating Ligninase Activity in Phanerochaete chrysosporium , 1986, Applied and environmental microbiology.

[21]  P. Fedorak,et al.  Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene , 1991, Applied and environmental microbiology.

[22]  J. Field,et al.  Screening for ligninolytic fungi applicable to the biodegradation of xenobiotics , 1993 .

[23]  R. K. Saugier,et al.  The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA. , 1983, Chemico-biological interactions.

[24]  M. Leisola,et al.  Oxidation of benzo(a)pyrene by extracellular ligninases of Phanerochaete chrysosporium. Veratryl alcohol and stability of ligninase. , 1986, The Journal of biological chemistry.

[25]  C. Cerniglia,et al.  Metabolism of phenanthrene by Phanerochaete chrysosporium , 1991, Applied and environmental microbiology.

[26]  M. Tien,et al.  Lignin peroxidase of Phanerochaete chrysosporium. Evidence for an acidic ionization controlling activity. , 1991, The Journal of biological chemistry.

[27]  M. Tien,et al.  Physical and enzymatic properties of lignin peroxidase isoenzymes from Phanerochaete chrysosporium , 1989 .

[28]  D. Westlake,et al.  Fungal Metabolism of n-Alkylbenzenes , 1986, Applied and environmental microbiology.

[29]  J. Bumpus Biodegradation of polycyclic hydrocarbons by Phanerochaete chrysosporium , 1989, Applied and environmental microbiology.

[30]  C. A. Reddy,et al.  Degradation of benzene, toluene, ethylbenzene, and xylenes (BTEX) by the lignin-degrading basidiomycete Phanerochaete chrysosporium , 1993, Applied and environmental microbiology.

[31]  J. Beynon,et al.  Studies of consecutive reactions of quinones in a reversed geometry mass spectrometer , 1981 .

[32]  W. Campbell,et al.  Stereoselective fungal metabolism of methylated anthracenes , 1990, Applied and environmental microbiology.

[33]  C. Cerniglia,et al.  Fungal metabolism of acenaphthene by Cunninghamella elegans , 1992, Applied and environmental microbiology.

[34]  G. Georgiou,et al.  Mineralization of biphenyl and PCBs by the white rot fungus Phanerochaete chrysosporium , 1992, Biotechnology and bioengineering.

[35]  H. Rosenstock,et al.  Energetics of Gaseous Ions , 1976 .

[36]  R. Neufeld,et al.  Degradation of fluorene in soil by fungus Phanerochaete chrysosporium , 1989, Biotechnology and bioengineering.

[37]  B. Kalyanaraman,et al.  Oxidation of polycyclic aromatic hydrocarbons and dibenzo[p]-dioxins by Phanerochaete chrysosporium ligninase. , 1986, The Journal of biological chemistry.

[38]  K. Hammel,et al.  Ring fission of anthracene by a eukaryote. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[39]  D. Westlake,et al.  Cytochrome c as a biocatalyst for the oxidation of thiophenes and organosulfides , 1993 .

[40]  Milton L. Lee,et al.  Mixed charge exchange-chemical ionization mass spectrometry of polycyclic aromatic hydrocarbons , 1977 .

[41]  M. Tien,et al.  LIGNIN PEROXIDASE FROM FUNGI : PHANEROCHAETE CHRYSOSPORIUM , 1990 .

[42]  E. Cavalieri,et al.  CHAPTER 10 – One-Electron and Two-Electron Oxidation in Aromatic Hydrocarbon Carcinogenesis , 1984 .