Identification of fluorpyrogallols as new intermediates in the biotransformation of monofluorphenols in Rh. opacus 1cp

Z.I. Finkelstein; B.P. Baskunov; M.G. Boersma; J. Vervoort; E.L. Golovlev; W.J.H. van Berkel; L.A. Golovleva; I.M.C.M. Rietjens

Identification of fluorpyrogallols as new intermediates in the biotransformation of monofluorphenols in Rh. opacus 1cp

Z.I. Finkelstein, B.P. Baskunov, M.G. Boersma, J. Vervoort, E.L. Golovlev, W.J.H. van Berkel, L.A. Golovleva, I.M.C.M. Rietjens

Research output: Contribution to journal › Article › Academic › peer-review

18 Citations (Scopus)

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 19F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The 19F 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.

Original language	English
Pages (from-to)	2148-2153
Journal	Applied and Environmental Microbiology
Volume	66
Publication status	Published - 2000

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@article{7ef1223a58554ca284b1acb5903a9f6b,

title = "Identification of fluorpyrogallols as new intermediates in the biotransformation of monofluorphenols in Rh. 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 19F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The 19F 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.",

author = "Z.I. Finkelstein and B.P. Baskunov and M.G. Boersma and J. Vervoort and E.L. Golovlev and {van Berkel}, W.J.H. and L.A. Golovleva and I.M.C.M. Rietjens",

year = "2000",

language = "English",

volume = "66",

pages = "2148--2153",

journal = "Applied and Environmental Microbiology",

issn = "0099-2240",

publisher = "American Society for Microbiology",

}

Identification of fluorpyrogallols as new intermediates in the biotransformation of monofluorphenols in Rh. opacus 1cp. / Finkelstein, Z.I.; Baskunov, B.P.; Boersma, M.G.; Vervoort, J.; Golovlev, E.L.; van Berkel, W.J.H.; Golovleva, L.A.; Rietjens, I.M.C.M.

In: Applied and Environmental Microbiology, Vol. 66, 2000, p. 2148-2153.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Identification of fluorpyrogallols as new intermediates in the biotransformation of monofluorphenols in Rh. opacus 1cp

AU - Finkelstein, Z.I.

AU - Baskunov, B.P.

AU - Boersma, M.G.

AU - Vervoort, J.

AU - Golovlev, E.L.

AU - van Berkel, W.J.H.

AU - Golovleva, L.A.

AU - Rietjens, I.M.C.M.

PY - 2000

Y1 - 2000

N2 - 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 19F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The 19F 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.

AB - 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 19F nuclear magnetic resonance demonstrated the formation of fluorocatechol and trihydroxyfluorobenzene derivatives from each of three monofluorophenols. The 19F 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.

M3 - Article

VL - 66

SP - 2148

EP - 2153

JO - Applied and Environmental Microbiology

JF - Applied and Environmental Microbiology

SN - 0099-2240

ER -