Turnover capacity of Coprinus cinereus peroxidase for phenol and monosubstituted phenols

Biotechnology Progress

Volumn 14, Issue 3, 1998, Pages 487-492

  Aitken, Michael D ^a   Heck, Phillip E ^a,b  

^a IL   (United States)

^b Montgomery watson Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INACTIVATION; PEROXIDASE; PHENOL DERIVATIVE; PHENOL; TURNOVER CAPACITY;

ACTIVATION ENERGY; DISSOCIATION; ENZYMES; HYDROGEN BONDS; HYDROGEN PEROXIDE; OXIDATION; PHENOLS;

COPRINUS CINEREUS PEROXIDASE; ENZYME CONSUMPTION; TURNOVER CAPACITY;

ENZYME IMMOBILIZATION;

COPRINUS CINEREUS;

EID: 0032077422     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp980034z     Document Type: Article

References (51)

1. Aitken, M. D.; Venkatadri, R.; Irvine, R. L. Oxidation of Phenolic Pollutants by a Lignin Degrading Enzyme from the White-Rot Fungus Phanerochaete chrysosporium. Water Res. 1989, 23, 443-450.
2. Aitken, M. D.; Massey, I. J.; Chen, T.; Heck, P. E. Characterization of Reaction Products from the Enzyme Catalyzed Oxidation of Phenolic Pollutants. Water Res. 1994, 28, 1879-1889.
3. Akkara, J. A.; Senecal, K. J.; Kaplan, D. L. Synthesis and Characterization of Polymers Produced by Horseradish PerS;oxidaso in Dioxane. J. Polym. Sci. 1991, 29, 1561-1574.
4. Al-Kassim, L.; Taylor, K. E.; Nicell, J. A.; Bewtra, J. K.; Biswas, N. Enzymatic Removal of Selected Aromatic Contaminants from Wastewater by a Fungal Peroxidase from Coprinus macrorhizus in Batch Reactors. J. Chem. Technoi Biotechnol. 1994, 61, 179-182.
5. Atlow, S. C. Bonadonna-Aparp, L.; Klibano, A. M. Dephenolizatipn of Industrial Wastewaters Catalyzed by Polyphenol Qxidase, Biotechnol. Bioeng. 1984, 26, 599-603.
6. Baynton, K. J.; Bewtra, J. K.; Biswas, K.; Taylor, K. E. Inactivation of Horseradish Peroxidase by Phenol and Hydrogen Peroxide: a Kinetic Investigation. Biochim. Biophys. Acta 1994, 1206, 272-278.
7. Berry, D. F.; Boyd, S. A. Qxidative Coupling of Phenols and Anilines by Peroxidase: Structure-Activity Relationships. Soil Sci. Soc. Am. J. 1984, 45, 565-569.
8. Bordwell, F. G.; Cheng, J.-P. Substituent Effects on the Stabilities of Phenoxyl Radicals and the Acidities of Phenoxyl Radical Cations, J. Am. Chem. Soc. 1991, 113, 1736-1743.
9. Carmichael, R.; Fedorak, P. M.; Pickard, M. A. Oxidation of Phenols by Chloroperoxidase. Biotechnol. Lett. 1985, 7, 289- 294.
10. Chen, G.-X.; Asada, K. Hydroxyurea and p-Aminophenol are the Suicide Inhibitors of Ascorbate Peroxidase. J. Biol. Chem. 1990, 265, 2775-2781.
11. Chung, N.; Aust, S. D. Inactivation of Lignin Peroxidase by Hydrogen Peroxide During the Oxidation of Phenols. Arch. Biochem. Biophys. 1995, 316, 851-855.
12. Cooper, V. A.; Nicell, J. A. Removal of Phenols from a Foundry Wastewater Using Horseradish Peroxidase. Water Res. 1996, 30, 954-964.
13. Dec, J.; Bollag, J.-M. Use of Plant Material for the Decontamination of Water Polluted with Phenols. Biotechnol. Bioeng. 1994, 44, 1132-1139.
14. DePillis, G. D.; Wariishi, H.; Gold, M. H.; Ortiz de Montellano, P. R. Inactivation of Lignin Peroxidase by Phenylhydrazine and Sodium Azide. Arch. Biochem. Biophys. 1990, 280, 217-223.
15. Divi, R. L.; Doerge, D. R. Mechanism-Based Inactivation of Lactoperoxidase and Thyroid Peroxidase by Resorcinol Derivatives. Biochemistry 1994, 33, 9668-9674.
16. Dunford, H. B.; Adeniran, A. J. Hammett ρσ Correlation for Reactions of Horseradish Peroxidase Compound II with Phenols. Arch. Biochem. Biophys. 1986, 251, 536-542.
17. . Scale Based Upon Spin Delocalization. J. Am. Chem. Soc. 1983, 105, 1221-1227 and 6531.
18. Goodhart, P. J.; DeWolf, W. E., Jr.; Kruse, L. I. Mechanism-Based Inactivation of Dopamine β-Hydroxylase by p-Cresol and Related Alkylphenols. Biochemistry 1987, 26, 2576-2583.
19. Hansch, C.; Leo, A. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology, American Chemical Society: Washington, DC, 1995.
20. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR. Hydrophobic, Electronic, and Steric Constants; American Chemical Society: Washington, DC, 1995.
21. Heck, P. E. Enzyme Catalyzed Oxidation of Phenolic Pollutants by Coprinus macrorhizus Peroxidase: Reaction Mechanisms, Kinetics and Product Characterization. Ph.D. Dissertation, University of North Carolina, Chapel Hill, NC, 1995.
22. Hewson, W. D.; Dunford, H. B. Stoichiometry of the Reaction Between Horseradish Peroxidase and p-Cresol. J. Biol. Chem. 1976, 251, 6043-6052.
23. Hiner, A. N. P.; Hernandez-Ruiz, J.; Arnao, M. B.; García-Cánovas, F.; Acosta, M. A. Comparative Study of the Purity, Enzyme Activity, and Inactivation by Hydrogen Peroxide of Commercially Available Horseradish Peroxidase Isoenzymes A and C. Biotechnol. Bioeng. 1996, 50, 655-662.
24. Job, D.; Dunford, H. B. Substituent Effect on the Oxidation of Phenols and Aromatic Amines by Horseradish Peroxidase Compound I. Eur. J. Biochem. 1976, 66, 607-614.
25. Kelder, P. P.; Fischer, M. J. E.; de Mol, N. J.; Janssen, L. H. M. Oxidation of Chlorpromazine by Methemoglobin in the Presence of Hydrogen Peroxide. Formation of Chlorpromazine Radical Cation and Its Covalent Binding to Methemoglobin. Arch. Biochem. Biophys. 1991, 284, 313-319.
26. Kjalke, M.; Andersen, M. B.; Schneider, P.; Christensen, B.; Schülein, M.; Welinder, K. G. Comparison of Structure and Activities of Peroxidases From Coprinus cinereus, Coprinus macrorhizus and Arthromyces ramosus. Biochim. Biophys. Acta 1992, 1120, 248-256.
27. Klibanov, A. M.; Tu, T.-M.; Scott, K. P. Peroxidase-Catalyzed Removal of Phenols From Coal-Conversion Waste Waters. Science 1983, 221, 259-261.
28. Kohler, H.; Jenzer, H. Interaction of Lactoperoxidase With Hydrogen Peroxide. Free Rad. Biol. Med. 1989, 6, 323-339.
29. Leatham, G. F.; King, V.; Stahmann, M. A. In Vitro Protein Polymerization by Quinohes or Free Radicals Generated by Plant or Fungal Oxidative Enzymes. Phytopathology 1980, 70, 1134-1140.
30. Mahoney, L. R.; DaRooge, M. A. Kinetic and Thermochemical Study of the Reaction of 2,4,6-Tri-tert-butylphenoxy Radical with Substituted Phenols, J. Am. Chem. Soc. 1970, 92, 890-899.
31. Maloney, S. W.; Manem, J.; Mallevialle, J.; Fiessinger, F. Transformation of Trace Organic, Compounds in Drinking Water by Enzymatic Oxidative Coupling. Environ. Sci. Technol. 1986, 20, 249-253.
32. Mason, H. S. Comparative Biochemistry of the Phenolase Complex. Adv. Enzymol. 1955, 16, 105-184.
33. Monzani, E.; Gatti, A. L.; Profumo, A.; Casella, L.; Gullotti, M. Oxidation of Phenolic Compounds by Lactoperoxidase. Evidence for the Presence of a Low-Potential Compound II During Catalytic Turnover. Biochemistry 1997, 36, 1918-1926.
34. Nakamoto, S.; Machida, N. Phenol Removal from Aqueous Solutions by Peroxidase-Catalyzed Reaction Using Additives. Water Res. 1992, 26, 49-54.
35. Nicell, J. A. Kinetics of Horseradish Peroxidase-Catalyzed Polymerization and Precipitation of Aqueous 4-Chlorophenol. J. Chem. Technol. Biotechnol. 1994, 60, 203-215.
36. Nicell, J. A.; Bewtra, J. K.; Biswas, N.; Taylor, E. Reactor Development for Peroxidase Catalyzed Polymerization and Precipitation of Phenols From Wastewater. Water Res. 1993, 27, 1629-1639.
37. Porter, D. J. T.; Bright, H. J. Ethanenitronate is a Peroxide-Dependent Suicide Substrate for Catalase. J. Biol. Chem. 1987, 262, 9608-9614.
38. Pütter, J.; Becker, R. Peroxidases. In Methods of Enzymatic Analysis, 3rd ed.; Bergmeyer, H. W., Ed.; Verlag-Chemie: Weinheim, Germany, 1983; Vol. 3, pp 286-293.
39. Rao, A. M.; John, V. T.; Gonzalez, R. D.; Akkara, J. A.; Kaplan, D. L. Catalytic and Interfacial Aspects of Enzymatic Polymer Synthesis in Reversed Micellar Systems. Biotechnol. Bioeng. 1993, 41, 531-540.
40. Ryu, K.; McEldoon, J. P.; Pokora, A. R.; Cyrus, W.; Dordick, J. S. Numerical and Monte Carlo Simulations of Phenolic Polymerizations Catalyzed by Peroxidase. Biotechnol. Bioeng. 1993, 42, 807-814.
41. Sakurada, J.; Sekiguchi, R.; Sato, K.; Hosoya, T. Kinetic and Molecular Orbital Studies on the Rate of Oxidation of Mono substituted Phenols and Anilines by Horseradish Peroxidase Compound II. Biochemistry 1990, 29, 4093-4098.
42. Seelbach, K.; Vandeurzen, M. P. J.; Vanrantwijk, F.; Sheldon, R.A.; Kragl, U. Improvement of the Total Turnover Number and Space-Time Yield for Chloroperoxidase Catalyzed Oxidation. Biotechnol. Bioeng. 1997, 55, 283-288.
43. Shuttleworth, K. L.; Bollag, J.-M. Soluble and Immobilized Laccase As Catalysts for the Transformation of Substituted Phenols. Enzyme Microb: Technol. 1986, 8, 171-177.
44. Siddique, M. H.; St. Pierre, C. C.; Biswas, N.; Bewtra, J. K.; Taylor, K. E. Immobilized Enzyme Catalyzed Removal of 4-Chlorophehol From Aqueous Solution. Water Res. 1993, 27, 883-890.
45. Tatsuimi, K.; Wada, S.; Ichikawa, H. Removal of Chlorpphenols From Wastewater by Immobilized Horseradish Peroxidase. Biotechnol. Bioeng. 1996, 51, 126-130.
46. Wayner, D. D. M.; Arnold, D. R. Substituent Effects on Benzyl Radical Hyperfine Coupling Constants. Part 2. The Effect of Sulphur Substituents. Can. J. Chem. 1984, 62, 1164-1108.
47. Wood, B. J. B.; Ingraham, L. L. Labelled Tyrosinase From Labelled Substrate. Nature 1965, 205, 291-292.
48. Wu, J.; Taylor, K. E.; Bewtra, J. K.; Biswas, N. Optimization of the Reaction Conditions for Enzymatic Removal of Phenol from Wastewater in the Presence of Polyethylene Glycol. Water Res. 1993, 27, 1701-1706.
49. Xu, F. Oxidation of Phenols, Anilines, and Benzenethiols by Fungal Laccases: Correlation Between Activity and Redox Potentials as well as Halide Inhibition. Biochemistry 1996, 35, 7608-7614.
50. Xu, Y.-P.; Huang, G.-L.; Yu, Y.-T. Kinetics of Phenolic Polymerization Catalyzed by Peroxidase in Organic Media. Biotechnol. Bioeng. 1995, 47, 117-119.
51. Young, L.; Yu, J. Ligninase-Catalyzed Decolorization of Synthetic Dyes. Water Res. 1997, 31, 1187-1193.