Investigations of enzymatic alterations of 2,4-dichlorophenol using 13C-nuclear magnetic resonance in combination with site-specific 13C- labeling: Understanding the environmental fate of this pollutant

Mark A. Nanny, Jacqueline M. Bortiatynski, Ming Tien, Patrick G. Hatcher

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The biodegradation of 13C-labeled 2,4-dichlorophenol (DCP labeled at the C-2 and C-6 positions), in the presence and absence of natural organic matter (NOM), by the white-rot fungus Phanerochaete chrysosporium, was examined using 13C-nuclear magnetic resonance (NMR). Using this method permitted the chemistry occurring at or near the labeled site to be followed. The formation of alkyl ethers and alkene ethers was observed. No aromatic by- products were detected, indicating that aromatic compounds are quickly degraded. Examining the reaction with time shows the exponential removal of 2,4-DCP and the consequential formation of labeled by products, whose concentration reaches a maximum just before all 2,4-DCP is consumed. After this, the by-products degrade exponentially. The presence of NOM causes 2,4- DCP to be removed from the aqueous phase more quickly than in its absence and also causes the by products to reach their maximum concentration much earlier. Degradation of the by products occurs at a much greater rate in the presence of NOM. One hypothesis for this behavior is that the NOM interacts with 2,4-DCP and its by-products, allowing them to be incorporated into the fungal biomass. 13C-nuclear magnetic resonance spectra of the fungal biomass after NaOH extraction show the presence of alkanes and a small amount of 2,4-DCP.

Original languageEnglish (US)
Pages (from-to)1857-1864
Number of pages8
JournalEnvironmental Toxicology and Chemistry
Volume15
Issue number11
DOIs
StatePublished - Nov 1 1996

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Environmental Pollutants
Ethers
environmental fate
Biomass
Labeling
Byproducts
nuclear magnetic resonance
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
Phanerochaete
organic matter
Biological materials
Alkanes
pollutant
Alkenes
ether
Fungi
alkene
biomass
alkane

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Health, Toxicology and Mutagenesis

Cite this

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title = "Investigations of enzymatic alterations of 2,4-dichlorophenol using 13C-nuclear magnetic resonance in combination with site-specific 13C- labeling: Understanding the environmental fate of this pollutant",
abstract = "The biodegradation of 13C-labeled 2,4-dichlorophenol (DCP labeled at the C-2 and C-6 positions), in the presence and absence of natural organic matter (NOM), by the white-rot fungus Phanerochaete chrysosporium, was examined using 13C-nuclear magnetic resonance (NMR). Using this method permitted the chemistry occurring at or near the labeled site to be followed. The formation of alkyl ethers and alkene ethers was observed. No aromatic by- products were detected, indicating that aromatic compounds are quickly degraded. Examining the reaction with time shows the exponential removal of 2,4-DCP and the consequential formation of labeled by products, whose concentration reaches a maximum just before all 2,4-DCP is consumed. After this, the by-products degrade exponentially. The presence of NOM causes 2,4- DCP to be removed from the aqueous phase more quickly than in its absence and also causes the by products to reach their maximum concentration much earlier. Degradation of the by products occurs at a much greater rate in the presence of NOM. One hypothesis for this behavior is that the NOM interacts with 2,4-DCP and its by-products, allowing them to be incorporated into the fungal biomass. 13C-nuclear magnetic resonance spectra of the fungal biomass after NaOH extraction show the presence of alkanes and a small amount of 2,4-DCP.",
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AB - The biodegradation of 13C-labeled 2,4-dichlorophenol (DCP labeled at the C-2 and C-6 positions), in the presence and absence of natural organic matter (NOM), by the white-rot fungus Phanerochaete chrysosporium, was examined using 13C-nuclear magnetic resonance (NMR). Using this method permitted the chemistry occurring at or near the labeled site to be followed. The formation of alkyl ethers and alkene ethers was observed. No aromatic by- products were detected, indicating that aromatic compounds are quickly degraded. Examining the reaction with time shows the exponential removal of 2,4-DCP and the consequential formation of labeled by products, whose concentration reaches a maximum just before all 2,4-DCP is consumed. After this, the by-products degrade exponentially. The presence of NOM causes 2,4- DCP to be removed from the aqueous phase more quickly than in its absence and also causes the by products to reach their maximum concentration much earlier. Degradation of the by products occurs at a much greater rate in the presence of NOM. One hypothesis for this behavior is that the NOM interacts with 2,4-DCP and its by-products, allowing them to be incorporated into the fungal biomass. 13C-nuclear magnetic resonance spectra of the fungal biomass after NaOH extraction show the presence of alkanes and a small amount of 2,4-DCP.

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