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 (19)F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The (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.affiliation: G. K. Skrybin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Russia.
authors.forename: Z I
authors.initials: ZI
authors.lastname: Finkelstein
authors.forename: B P
authors.initials: BP
authors.lastname: Baskunov
authors.forename: M G
authors.initials: MG
authors.lastname: Boersma
authors.forename: J
authors.initials: J
authors.lastname: Vervoort
authors.forename: E L
authors.initials: EL
authors.lastname: Golovlev
authors.forename: W J
authors.initials: WJ
authors.lastname: van Berkel
authors.forename: L A
authors.initials: LA
authors.lastname: Golovleva
authors.forename: I M
authors.initials: IM
authors.lastname: Rietjens
mesh_terms: D001711:Biotransformation; D002855:Chromatography, Thin Layer; D005459:Fluorides / Q000378:metabolism*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010636:Phenols / Q000378:metabolism*; D011748:Pyrogallol / Q000378:metabolism*; D012240:Rhodococcus / Q000254:growth & development / Q000378:metabolism*
chemical_list: D010636:Phenols; D011748:Pyrogallol; D005459:Fluorides