Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290.

Doreen Waldau, Annett Mikolasch, Michael Lalk, Frieder Schauer

Institute of Microbiology and Molecular Biology, Department of Applied Microbiology, Ernst-Moritz-Arndt-University, Friedrich-Ludwig-Jahn-Strasse 15, 17487 Greifswald, Germany. doreen.waldau@uni-greifswald.de

Applied microbiology and biotechnology 2009 May

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Different 9H-carbazole derivatives have been investigated within the last decades due to their broad range of pharmacological applications. While the metabolism of 9H-carbazole has previously been reported, nothing was known about the bacterial transformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole. Thus, for the first time, the bacterial biotransformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole was analyzed using biphenyl-grown cells of Ralstonia sp. strain SBUG 290 expressing biphenyl 2,3-dioxygenase. This strain accumulated 3-hydroxy-1,2,3,5,6,7,8,9-octahydrocarbazol-4-one and 6'-iminobicyclohexylidene-2',4'-dien-2-one as major products during the incubation with 2,3,4,9-tetrahydro-1H-carbazole. Carbazol-9-yl-methanol was verified as the primary oxidation product of 9-methyl-9H-carbazole. In addition, 9H-carbazol-1-ol, 9H-carbazol-3-ol, and 3-hydroxy-1,2,3,9-tetrahydrocarbazol-4-one where detected in lower concentrations during the transformation of carbazol-9-yl-methanol and 9-methyl-9H-carbazole. Products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, as well as (1)H and (13)C nuclear magnetic resonance analyses.

Citation

Doreen Waldau, Annett Mikolasch, Michael Lalk, Frieder Schauer. Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290. Applied microbiology and biotechnology. 2009 May;83(1):67-75