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

Abstract

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 1H and 13C nuclear magnetic resonance analyses.

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Acknowledgements

This study was supported by the scholarship program of the German Federal Environmental Foundation (DBU).

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Correspondence to Doreen Waldau.

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Waldau, D., Mikolasch, A., Lalk, M. et al. Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290. Appl Microbiol Biotechnol 83, 67–75 (2009). https://doi.org/10.1007/s00253-008-1853-z

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Keywords

  • Biotransformation
  • Heterocyclic compounds
  • Biphenyl 2,3-dioxygenase (BDO)
  • 2,3,4,9-Tetrahydro-1H-carbazole
  • 9-Methyl-9H-carbazole
  • Carbazol-9-yl-methanol