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Title: Identification of fluoropyrogallols as new intermediates in biotransformation of monofluorophenols in Rhodococcus opacus 1cp

Abstract

The transformation of monofluorophenols by whole cells of Rhodococcus opacus 1cp was investigated, with special emphasis on the nature of hydroxylated intermediates formed. Thin-layer chromatography, mass spectrum analysis, and {sup 19}F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The {sup 19}F chemical shifts and proton-coupled splitting patterns of the fluorine resonances of the trihydroxyfluorobenzene products established that the trihydroxylated aromatic metabolites contained hydroxyl substituents on three adjacent carbon atoms. Thus, formation of 1,2,3-trihydroxy-4-fluorobenzene (4-fluoropyrogallol) from 2-fluorophenol and formation of 1,2,3-trihydroxy-5-fluorobenzene (5-fluoropyrogallol) from 3-fluorophenol and 4-fluorophenol were observed. These results indicate the involvement of fluoropyrogallols as previously unidentified metabolites in the biotransformation of monofluorophenols in R. opacus 1cp.

Authors:
; ; ; ; ; ; ;
Publication Date:
Research Org.:
Russian Academy of Sciences, Pushchino (RU)
OSTI Identifier:
20075764
Resource Type:
Journal Article
Journal Name:
Applied and Environmental Microbiology
Additional Journal Information:
Journal Volume: 66; Journal Issue: 5; Other Information: PBD: May 2000; Journal ID: ISSN 0099-2240
Country of Publication:
United States
Language:
English
Subject:
54 ENVIRONMENTAL SCIENCES; SOILS; BIODEGRADATION; REMEDIAL ACTION; ORGANIC HALOGEN COMPOUNDS; PHENOLS; RHODOCOCCUS; METABOLITES; CHEMICAL ANALYSIS

Citation Formats

Finkelstein, Z.I., Baskunov, B.P., Boersma, M.G., Vervoort, J., Golovlev, E.L., Berkel, W.J.H. van, Golovleva, L.A., and Rietjens, I.M.C.M. Identification of fluoropyrogallols as new intermediates in biotransformation of monofluorophenols in Rhodococcus opacus 1cp. United States: N. p., 2000. Web. doi:10.1128/AEM.66.5.2148-2153.2000.
Finkelstein, Z.I., Baskunov, B.P., Boersma, M.G., Vervoort, J., Golovlev, E.L., Berkel, W.J.H. van, Golovleva, L.A., & Rietjens, I.M.C.M. Identification of fluoropyrogallols as new intermediates in biotransformation of monofluorophenols in Rhodococcus opacus 1cp. United States. doi:10.1128/AEM.66.5.2148-2153.2000.
Finkelstein, Z.I., Baskunov, B.P., Boersma, M.G., Vervoort, J., Golovlev, E.L., Berkel, W.J.H. van, Golovleva, L.A., and Rietjens, I.M.C.M. Mon . "Identification of fluoropyrogallols as new intermediates in biotransformation of monofluorophenols in Rhodococcus opacus 1cp". United States. doi:10.1128/AEM.66.5.2148-2153.2000.
@article{osti_20075764,
title = {Identification of fluoropyrogallols as new intermediates in biotransformation of monofluorophenols in Rhodococcus opacus 1cp},
author = {Finkelstein, Z.I. and Baskunov, B.P. and Boersma, M.G. and Vervoort, J. and Golovlev, E.L. and Berkel, W.J.H. van and Golovleva, L.A. and Rietjens, I.M.C.M.},
abstractNote = {The transformation of monofluorophenols by whole cells of Rhodococcus opacus 1cp was investigated, with special emphasis on the nature of hydroxylated intermediates formed. Thin-layer chromatography, mass spectrum analysis, and {sup 19}F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The {sup 19}F chemical shifts and proton-coupled splitting patterns of the fluorine resonances of the trihydroxyfluorobenzene products established that the trihydroxylated aromatic metabolites contained hydroxyl substituents on three adjacent carbon atoms. Thus, formation of 1,2,3-trihydroxy-4-fluorobenzene (4-fluoropyrogallol) from 2-fluorophenol and formation of 1,2,3-trihydroxy-5-fluorobenzene (5-fluoropyrogallol) from 3-fluorophenol and 4-fluorophenol were observed. These results indicate the involvement of fluoropyrogallols as previously unidentified metabolites in the biotransformation of monofluorophenols in R. opacus 1cp.},
doi = {10.1128/AEM.66.5.2148-2153.2000},
journal = {Applied and Environmental Microbiology},
issn = {0099-2240},
number = 5,
volume = 66,
place = {United States},
year = {2000},
month = {5}
}