Products of laccase catalyzed reaction of 1-hydroxypyrene

Toxicological and Environmental Chemistry

Volumn 87, Issue 4, 2005, Pages 583-593

  Roper, J Chadwick ^a   Pfaender, Frederic K ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

Humification; Hydroxypyrene; Laccase; PAHs; Polymerization

Indexed keywords

ACETONITRILE; CATALYSIS; HYDROPHOBICITY; IMPURITIES; KETONES; PHOTODIODES; SOILS;

HUMIFICATION; HYDROXYPYRENES; LACCASE; PAHS; PHOTO-OXIDATION PRODUCTS; PYRENE;

ENZYMES;

HUMIFICATION;

INVERTEBRATA;

EID: 30444439868     PISSN: 02772248     EISSN: 10290486     Source Type: Journal    
DOI: 10.1080/02772240500423888     Document Type: Article

References (33)

1. Hedges J. Humic substances and their role in the natural environment. John Wiley and Sons Ltd.: New York; 1988. pp 45-58.
2. Nannipieri P, Bollag J-M. Use of enzymes to detoxify pesticide- contaminated soils and waters. J Environ Qual 1991;20:510-517.
3. Verstraete W, Devliegher W. Formation of non-bioavailable organic residues in soil: Perspectives for site remediation. Biodeg 1996;7:471-485.
4. Bollag J-M, Meyers C. Detoxification of aquatic and terrestrial sites through binding of pollutants to humic substances. Sci. Total Environ. 1992;117/118:357-366.
5. Cerniglia C. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 1992;3:338-351.
6. Howsam M, VanStraalen NM. Pyrene Metabolism in the springtail Orchesella cinta L. (Collembola, Entomobrydiae). Environ. Toxicol. Chem. 2002;22:1481-1486.
7. Belkin S, Steiber M, Tiehm A, Frimmel F, Abeliovich A, Werner P, Ulitzur S. Toxicity and genotoxicity enhancement during polycyclic aromatic hydrocarbons' degradation. Environ Toxicol Water Qual 1994;9:303-309.
8. Lambert M, Kremer S, Anke H. Antimicrobial, phytotoxic, nematicidal, cytotoxic, and mutagenic activities of 1-hydroxypyrene, the initial metabolite in pyrene metabolism by the Basdiomycete Crinipellis Stipitaria. Bull of Env Contam Toxicol 1995;55:251-257.
9. Richnow H, Seifert R, Hefter J, Link M, Francke W, Schaefer G, Michaelis W. Organic pollutants associated with macromolecular soil organic matter: Mode of binding. Org. Geochem. 1997;26:745-758.
10. Kirso U, Irha N. Role of algae in fate of carcinogenic polycyclic aromatic hydrocarbons in the aquatic environment. Ecotox Env Saf 1998;41:83-89.
11. Roper JC, Pfaender FK. Pyrene and chrysene fate in surface soil and sand microcosms. Environ. Toxicol. Chem. 2001;20:223-230.
12. Dec J, Bollag J-M. Dehalogenation of chlorinated phenols during oxidative coupling. Environ. Sci. Tech. 1994;28:484-490.
13. Gianfreda L, Xu F, Bollag J-M. Laccases: A useful group of oxidoreductive enzymes. Biorem J 1999;3:1-25.
14. Pal S, Bollag J-M, Huang P. Role of abiotic and biotic catalysts in the transformation of phenolic compounds through oxidative coupling reactions. Soil Biol and Biochem 1994;26:813-820.
15. Ressler B, Kneifel H, Winter J. Bioavailability of polycyclic aromatic hydrocarbons and formation of humic acid-like residues during bacterial PAH degradation. Appl Microbiol Biotechnol 1999;53:85-91.
16. Klibanov A, Tu T-M, Scott K. Peroxidase-catalyzed removal of phenols from coal-conversion waste waters. Science 1983;221:259-261.
17. Berry D, Boyd S. Decontamination of soil through enhanced formation of bound residues. Environ. Sci. Tech. 1985;19:1132-1133.
18. Tatsumi K, Freyer A, Minard R, Bollag J-M. Enzyme mediated coupling of 3,4-dichloroaniline and ferulic acid: A model for pollutant binding to humic materials. Environ. Sci. Tech. 1994;28:210-215.
19. Roper J, Sarkar J, Dec J, Bollag, J-M. Enhanced enzymatic removal of chlorophenols in the presence of co-substrates. Water Res. 1995;29:2720-2724.
20. Kazunga C, Aitken M, Gold A. Primary product of the horseradish peroxidase catalyzed oxidation of pentachlorophenol. Environ. Sci. Tech. 1999;33:1408-1412.
21. Bollag J-M, Liu S-Y, Minard R. Cross coupling of phenolic humus constituents and 2,4-dichlorophenol. J Soil Sci Soc of Am 1980;44:52-56.
22. Hoff T, Liu S-Y, Bollag J-M. Transformation of halogen-, alkyl-, and alkoxy-substituted anilines by a laccase of Trametes versicolor. Appl Env Biol 1985;49:1040-1045.
23. Simmons K, Minard R, Bollag J-M. Oxidative co-oligomerization of guaiacol and 4-chloroaniline. Environ. Sci. Tech. 1989;23:115-121.
24. 13C labeled 2,4-dichlorophenol to humic substances. Environ. Sci. Tech. 1993;27:2098-2103.
25. 13C NMR. In: Senesei N, Miano TM, editors. Humic Substances in the Global Environment and Implications on Human Health. Elsevier; 1994. pp 1091-1099.
26. 14C]Anthracene in Soil. Appl. Environ. Microbiol. 1999;65:1834-1842.
27. Richnow, H, Eschenbach, A, Mahro, B, Kaestner, M, Annweiler, E, Seifert, R, Michaelis, W. Formation of nonextractable soil residues: A stable isotope approach. Environ. Sci. Tech. 1999; 33:3761-3767.
28. 13C NMR. Environ. Sci. Tech. 1999;33:119-125.
29. 13C NMR T1 relaxation measurements. Environ. Sci. Tech. 1997;31:530-534.
30. Alexander M. How toxic are toxic chemicals in soil? Environ. Sci. Tech. 1995; 29:2713-2717.
31. Cho H, Harvey R. Synthesis of hydroquinone diacetates from polycyclic aromatic quinines. J. Chem. Soc. Perkin Trans. I 1976;10:836-839.
32. Kazunga C, Aitken MD, Gold A, Sangaiah R. Fluoranthene-2,3 and 1,5 diones are novel products from the bacterial transformation of fluoranthene. Environ. Sci. Tech. 2001;35:917-922.
33. 13C-CPMAS-NMR-spectroscopy: Evidence of covalent bonds. Chemosphere 2002;48:117-131.