Degradation of 4-fluorobiphenyl by mycorrhizal fungi as determined by F-19 nuclear magnetic resonance spectroscopy and C-14 radiolabelling analysis

N A Green, A A Meharg, C Till, J Troke, J K Nicholson

Research output: Contribution to journalArticle

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Abstract

The pathways of biotransformation of 4-fluorobiphenyl (4FBP) by the ectomycorrhizal fungus Tylospora fibrilosa and several other mycorrhizal fungi were investigated by using F-19 nuclear magnetic resonance (NMR) spectroscopy in combination with C-14 radioisotope-detected high-performance liquid chromatography (C-14-HPLC). Under the conditions used in this study T. fibrillosa and some other species degraded 4FBP. C-14-HPLC profiles indicated that there were four major biotransformation products, whereas 19F NMR showed that there were six major fluorine-containing products. We confirmed that 4-fluorobiphen-4'-ol and 4-fluorobiphen-3'-ol were two of the major products formed, but no other products were conclusively identified. There was no evidence for the expected biotransformation pathway (namely, meta cleavage of the less halogenated ring), as none of the expected products of this route were found. To the best of our knowledge, this is the first report describing intermediates formed during mycorrhizal degradation of halogenated biphenyls.

Original languageEnglish
Pages (from-to)4021-4027
Number of pages7
JournalApplied and Environmental Microbiology
Volume65
Issue number9
Publication statusPublished - Sep 1999

Keywords

  • ECTOMYCORRHIZAL FUNGI
  • PHANEROCHAETE-CHRYSOSPORIUM
  • FLUORINATED XENOBIOTICS
  • MICROBIAL-DEGRADATION
  • NMR
  • 3,3',4,4'-TETRACHLOROBIPHENYL
  • MINERALIZATION
  • METABOLISM
  • ATRAZINE
  • BIPHENYL

Cite this

Degradation of 4-fluorobiphenyl by mycorrhizal fungi as determined by F-19 nuclear magnetic resonance spectroscopy and C-14 radiolabelling analysis. / Green, N A ; Meharg, A A ; Till, C ; Troke, J ; Nicholson, J K .

In: Applied and Environmental Microbiology, Vol. 65, No. 9, 09.1999, p. 4021-4027.

Research output: Contribution to journalArticle

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abstract = "The pathways of biotransformation of 4-fluorobiphenyl (4FBP) by the ectomycorrhizal fungus Tylospora fibrilosa and several other mycorrhizal fungi were investigated by using F-19 nuclear magnetic resonance (NMR) spectroscopy in combination with C-14 radioisotope-detected high-performance liquid chromatography (C-14-HPLC). Under the conditions used in this study T. fibrillosa and some other species degraded 4FBP. C-14-HPLC profiles indicated that there were four major biotransformation products, whereas 19F NMR showed that there were six major fluorine-containing products. We confirmed that 4-fluorobiphen-4'-ol and 4-fluorobiphen-3'-ol were two of the major products formed, but no other products were conclusively identified. There was no evidence for the expected biotransformation pathway (namely, meta cleavage of the less halogenated ring), as none of the expected products of this route were found. To the best of our knowledge, this is the first report describing intermediates formed during mycorrhizal degradation of halogenated biphenyls.",
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AU - Nicholson, J K

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N2 - The pathways of biotransformation of 4-fluorobiphenyl (4FBP) by the ectomycorrhizal fungus Tylospora fibrilosa and several other mycorrhizal fungi were investigated by using F-19 nuclear magnetic resonance (NMR) spectroscopy in combination with C-14 radioisotope-detected high-performance liquid chromatography (C-14-HPLC). Under the conditions used in this study T. fibrillosa and some other species degraded 4FBP. C-14-HPLC profiles indicated that there were four major biotransformation products, whereas 19F NMR showed that there were six major fluorine-containing products. We confirmed that 4-fluorobiphen-4'-ol and 4-fluorobiphen-3'-ol were two of the major products formed, but no other products were conclusively identified. There was no evidence for the expected biotransformation pathway (namely, meta cleavage of the less halogenated ring), as none of the expected products of this route were found. To the best of our knowledge, this is the first report describing intermediates formed during mycorrhizal degradation of halogenated biphenyls.

AB - The pathways of biotransformation of 4-fluorobiphenyl (4FBP) by the ectomycorrhizal fungus Tylospora fibrilosa and several other mycorrhizal fungi were investigated by using F-19 nuclear magnetic resonance (NMR) spectroscopy in combination with C-14 radioisotope-detected high-performance liquid chromatography (C-14-HPLC). Under the conditions used in this study T. fibrillosa and some other species degraded 4FBP. C-14-HPLC profiles indicated that there were four major biotransformation products, whereas 19F NMR showed that there were six major fluorine-containing products. We confirmed that 4-fluorobiphen-4'-ol and 4-fluorobiphen-3'-ol were two of the major products formed, but no other products were conclusively identified. There was no evidence for the expected biotransformation pathway (namely, meta cleavage of the less halogenated ring), as none of the expected products of this route were found. To the best of our knowledge, this is the first report describing intermediates formed during mycorrhizal degradation of halogenated biphenyls.

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