Biological, thermal and photochemical transformation of 2-trifluoromethylphenol |
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Authors: | Uwe Michael Reinscheid Han Zuilhof Rudolf Müller Jacques Vervoort |
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Affiliation: | (1) Department of Biochemistry, Wageningen Agricultural University, Dreijenlaan 3, NL-6708 HA Wageningen, The Netherlands;(2) Department of Organic Chemistry, Wageningen Agricultural University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands;(3) Department of Biotechnology and Technical Biochemistry, Technical University Hamburg-Harburg, Denickestrase 15, D-21073 Hamburg, Germany |
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Abstract: | This is the first report on the metabolism of trifluoromethyl aromatics in a thermophilic bacterium, Bacillus thermoleovorans A2. Enzymes of the phenol degradation pathway are induced when cultivating Bacillus thermoleovorans A2 on complex medium. Direct measurements of fluorinated xenobiotics in cell suspensions using 19F-NMR made it possible to follow quantitatively the biotransformation routes. During the biotransformation of 2-CF3-phenol by B. thermoleovorans A2, a fluorinated metabolite, 2-hydroxy-6-oxo-7,7,7,-trifluorohepta-2,4-dienoate (7-TFHOD), accumulated. This metabolite is transformed non-enzymatically when exposed to sunlight. The accumulation of 7-TFHOD as an intermediate in the 2-CF3-phenol pathway was rationalized by calculating molecular properties of a series of meta-cleavage products. |
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Keywords: | Bacillus biotransformation NMR thermophilic trifluoromethylphenol |
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