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Main Title Oxidative 4-Dechlorination of Polychlorinated Phenols Is Catalyzed by Extracellular Fungal Lignin Peroxidases (Journal Version).
Author Hammel, K. E. ; Tardone, P. J. ;
CORP Author State Univ. of New York at Syracuse. Coll. of Environmental Science and Forestry.;Environmental Protection Agency, Cincinnati, OH. Risk Reduction Engineering Lab.
Publisher c1988
Year Published 1988
Report Number EPA/600/J-88/268;
Stock Number PB89-142707
Additional Subjects Air pollution ; Aromatic polycyclic hydrocarbons ; Phenols ; Lignin ; Peroxidases ; Biodeterioration ; Contaminants ; Basidiomycetes ; Fungi ; Oxidation ; Dechlorination ; Catalysts ; Reprints ; Air purification ; Phanerochaete chrysosporium
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NTIS  PB89-142707 Some EPA libraries have a fiche copy filed under the call number shown. 07/26/2022
Collation 7p
Abstract The extracellular lignin peroxidases (ligninases) of Phanerochaete chrysosporium catalyzed H2O2-dependent spectral changes in several environmentally significant polychlorinated phenols: 2,4-dichloro-,2,4,5-trichloro-, and pentachlorophenol. Gas chromatography/mass spectrometry showed that lignin peroxidase catalyzed a 4-dechlorination of the starting phenol to yield a p-benzoquinone. The oxidation of 2,4-dichlorophenol also yielded a dechlorinated coupling dimer, tentatively identified as 2-chloro-6-(2,4-dichlorophenoxyl)-p-benzoquinone. Experiments on the stoichiometry of 2,4,6-trichlorophenol oxidation showed that this substrate was quantitatively dechlorinated to give the quinone and inorganic chloride. H2(sup 18)O-labeling experiments on 2,4,6-trichlorophenol oxidation demonstrated that water was the source of the new 4-oxo substituent in 2,6-dichloro-p-benzoquinone. Results indicate a mechanism whereby lignin peroxidase oxidizes a 4-chlorinated phenol to an electrophilic intermediate, perhaps the 4-chlorocyclohexadienone cation. Nucleophilic attack by water and elimination of HCl then ensue at the 4-position, which produces the quinone. It appears that these peroxidases could also catalyze the initial dechlorination of certain polychlorinated phenols in vivo. (Copyright (c) 1988 American Chemical Society.)
Supplementary Notes Sponsored by Environmental Protection Agency, Cincinnati, OH. Risk Reduction Engineering Lab.
Availability Notes Pub. in Biochemistry, v27 p6563-6568 1988.
NTIS Title Notes Journal article.
Title Annotations Reprint: Oxidative 4-Dechlorination of Polychlorinated Phenols Is Catalyzed by Extracellular Fungal Lignin Peroxidases (Journal Version).
Category Codes 68A; 57C; 99D
NTIS Prices Not available NTIS
Primary Description 600/14
Document Type NT
Cataloging Source NTIS/MT
Control Number 908926906
Origin NTIS
Type CAT