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

The transformation of monofluorophenols by whole cells of Rhodococcus opacu s 1cp was investigated, with special emphasis on the nature of hydroxylated intermediates formed. Thin-layer chromatography, mass spectrum analysis, a nd F-19 nuclear magnetic resonance demonstrated the formation of fluorocate chol and trihydroxyfluorobenzene derivatives from each of three monofluorop henols. The F-19 chemical shifts and proton-coupled splitting patterns of t he fluorine resonances of the trihydroxyfluorobenzene products established that the trihydroxylated aromatic metabolites contained hydroxyl substituen ts on three adjacent carbon atoms. Thus, formation of 1,2,3-trihydroxy-4-fl uorobenzene (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 fluor opyrogallols as previously unidentified metabolites in the biotransformatio n of monofluorophenols in R. opacus 1cp.