F-19 NUCLEAR-MAGNETIC-RESONANCE AS A TOOL TO INVESTIGATE MICROBIAL-DEGRADATION OF FLUOROPHENOLS TO FLUOROCATECHOLS AND FLUOROMUCONATES

A method was developed to study the biodegradation and oxidative biode halogenation of fluorinated phenols by F-19 nuclear magnetic resonance (NMR). Characterization of the F-19 NMR spectra of metabolite profile s of a series of fluorophenols, converted by purified phenol hydroxyla se, catechol 1,2-dioxygenase, and/or by the yeast-like fungus Exophial a jeanselmei, provided possibilities for identification of the F-19 NM R chemical shift values of fluorinated catechol and muconate metabolit es. As an example, the F-19 NMR method thus defined was used to charac terize the time-dependent metabolite profiles of various halophenols i n either cell extracts or in incubations with whole cells of E. jeanse lmei. The results obtained for these two systems are similar, except f or the level of muconates observed. Altogether, the results of the pre sent study describe a F-19 NMR method which provides an efficient tool for elucidating the metabolic pathways for conversion of fluorine-con taining phenols by microorganisms, with special emphasis on possibilit ies for biodehalogenation and detection of the type of fluorocatechols and fluoromuconates involved. In addition, the method provides possib ilities for studying metabolic pathways in vivo in whole cells.