Biohydroxylation of N,N-dialkylarylamines by the isolated topsoil bacterium Bacillus megaterium |
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Authors: | Marcus Taupp Frank Heckel Dag Harmsen Peter Schreier |
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Institution: | aInstitute of Food Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany bDepartment of Periodontology, University Hospital Münster, Waldeyerstr. 30, 48149 Münster, Germany |
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Abstract: | Topsoil microorganisms were screened for their acceptability of the standard substrate N,N-dimethylaniline in bacterial ‘whole-cell’ incubations. One bacterium converted N,N-dimethylaniline and was identified as Bacillus megaterium by 16S rDNA analysis and DNA/DNA-hybridization. In contrast to the well-known C-hydroxylation by liver microsomes, leading to p-hydroxylation, B. megaterium formed o- and p-monohydroxylated products, i.e. N,N-dimethyl-2-aminophenol and N,N-dimethyl-4-aminophenol, both identified by gas chromatography–mass spectrometry (GC–MS) using synthesized reference compounds. The observed hydroxylation showed slight regioselectivity in favour of the o-hydroxylated product. Two further substrates, N,N-diethylaniline and N-ethyl-N-methylaniline, were also successfully biohydroxylated by B. megaterium with corresponding regioselectivity. Interestingly, aniline, known to be transformed easily by cytochrome P-450meg into p-aminophenol, was not accepted as substrate. |
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Keywords: | Bacillus megaterium Biohydroxylation N N-Dialkylarylamines N N-Dialkyl-2-aminophenols N N-Dialkyl-4-aminophenols |
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