Fungal Metabolism of Toluene: Monitoring of Fluorinated Analogs by 19F Nuclear Magnetic Resonance Spectroscopy

Applied and Environmental Microbiology

Volumn 67, Issue 3, 2001, Pages 1030-1034

  Prenafeta Boldú, Francesc X ^a   Luykx, Dion M A M ^a   Vervoort, Jacques ^a   De Bont, Jan A M ^b  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b FRIESLANDCAMPINA   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE; TOLUENE;

ARTICLE; BIOREMEDIATION; CULTURE MEDIUM; FUNGUS; GROWTH, DEVELOPMENT AND AGING; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BIODEGRADATION, ENVIRONMENTAL; CULTURE MEDIA; FLUORINE RADIOISOTOPES; FUNGI; MAGNETIC RESONANCE SPECTROSCOPY; TOLUENE;

EID: 0035286746     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.67.3.1030-1034.2001     Document Type: Article

References (25)

1. Auret, B. J., D. R. Boyd, P. M. Robinson, and C. G. Watson. 1971. The NIH shift during the hydroxylation of aromatic substrates by fungi. Chem. Commun. 24:1585-1587.
2. 19F nuclear magnetic resonance as a tool to investigate microbial degradation of fluorophenols to fluorocatechols and fluoromuconates. Appl. Environ. Microbiol. 64:1256-1263.
3. 19F NMR study on the biodegradation of fluorophenols by various Rhodococcus species. Biodegradation 9:475-486.
4. Cain, R. B., R. F. Bilton, and J. A. Darrah. 1968. The metabolism of aromatic acids by microorganisms. Metabolic pathways in the fungi. Biochem. J. 108:797-828.
5. Cerniglia, C. E., P. P. Fu, and S. K. Yang. 1983. Regio- and stem-selective metabolism of 4-methylbenz(a)anthracene by the fungus Cunninghamella elegans. Biochem. J. 216:377-384.
6. Cerniglia, C. E., K. J. Lambert, D. W. Miller, and J. P. Freeman. 1984. Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans. Appl. Environ. Microbiol. 47:111-118.
7. Cerniglia, C. E., D. W. Miller, S. K. Yang, and J. P. Freeman. 1984. Effects of a fluoro substituent on the fungal metabolism of 1-fluoronaphthalene. Appl. Environ. Microbiol. 48:294-300.
8. Cerniglia, C. E., J. B. Sutherland, and S. A. Crow. 1991. Fungal metabolism of aromatic hydrocarbons, p. 193. In G. Winkelmann (ed.), Microbial degradation of natural products. VCH Verlagsgesellschaft, Weinheim, Germany.
9. Gibson, D. T., M. Henley, H. Yoshioka, and T. J. Mabry. 1970. Formation of (+)-cis-2,3-dihydroxy-1-methyl-cyclohexa-4,6,-diene from toluene by Pseudomonas putida. Biochemistry 9:1626-1630.
10. Hartmans, S., M. J. van der Werf, and J. A. M. de Bont. 1990. Bacterial degradation of styrene involving a novel flavin adenine dinucleotide-dependent styrene monooxygenase. Appl. Environ. Microbiol. 56:1347-1351.
11. Holland, H. L., E. J. Bergen, P. C. Chenchaiah, S. H. Khan, B. Munoz, R. W. Ninniss, and D. Richards. 1987. Side chain hydroxylation of aromatic compounds by fungi. 1. Products and stereochemistry. Can. J. Chem. 65:502-507.
12. Holland, H. L., F. M. Brown, B. Munoz, and R. W. Ninniss. 1988. Side chain hydroxylation of aromatic hydrocarbons by fungi. Part 2: isotope effects and mechanism. J. Chem. Soc. Perkin Trans. II 1988:1557-1563.
13. Peelen, S., I. M. C. M. Rietjens, M. G. Boersma, and J. Vervoort. 1995. Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. A comparison of regioselectivity and rate of conversion with calculated molecular orbital substrate characteristics. Eur. J. Biochem. 227:284-291.
14. Prenafeta-Boldú, F. X., A. Kuhn, D. M. A. M. Luykx, H. Anke, J. W. van Groenestijn, and J. A. M. de Bont. Isolation and characterisation of fungi growing on volatile aromatic hydrocarbons as their sole carbon and energy source. Mycol. Res., in press.
15. Rietjens, I. C. M. M., N. H. P. Cnubben, M. van Haandel, B. Tyrakowska, A. E. M. F. Soffers, and J. Vervoort. 1995. Different metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene compared to molecular orbital substrate characteristics. Chem.-Biol. Interact. 94:49-72.
16. Shields, S. M., S. O. Montgomery, P. J. Chapman, S. M. Cuskey, and P. H. Pritchard. 1989. Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium G4. Appl. Environ. Microbiol. 55:1624-1629.
17. Smith, R. V., and J. P. Rosazza. 1974. Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch. Biochem. Biophys. 161:551-558.
18. van Berkel, W. J. H., M. H. M. Eppink, W. J. Middelhoven, J. Vervoort, and I. M. C. M. Rietjens. 1994. Catabolism of 4-hydroxybenzoate in Candida parapsilosis proceeds through initial oxidative decarhoxylation by a FAD-dependent 4-hydroxybenzoate 1-hydroxylase. FEMS Microbiol. Lett. 121:207-216.
19. 19F-NMR method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline. Xenobiotica 20:657-670.
20. Weber, V. J., K. C. Hage, and J. A. M. de Bont. 1995. Growth of the fungus Cladosporium shaerospermum with toluene as the sole carbon and energy source. Appl. Environ. Microbiol. 61:3562-3566.
21. Whals, C. 1982. Fluorinated substrate analogs: routes of metabolism and selective toxicity. Adv. Enzymol. 55:197-289.
22. Whited, G. M., and D. T. Gibson. 1991. Separation and partial characterization of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1. J. Bacteriol. 173:3017-3020.
23. Worsey, M. J., and P. A. Williams. 1975. Metabolism of toluene and xylenes by Pseudomonas putida (arvilla) mt-2: evidence for a new function of the TOL plasmid. J. Bacteriol. 124:7-13.
24. Wright, J. D., and C. Ratledge. 1991. Isolation of two Rhodotorula rubra strains showing differences in the degradation of aromatic compounds. Appl. Microbiol. Biotechnol. 35:94-99.
25. Yadav, J. S., and C. A. Reddy. 1993. Degradation of benzene, toluene, ethylhenzene, and xylenes (BTEX) by the lignin-degrading basidiomycete Phanerochaete chrysosporium. Appl. Environ. Microbiol. 59:756-762.