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Characterization of new oxidation products of 9H-carbazole and structure related compounds by biphenyl-utilizing bacteria

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Abstract

9H-Carbazole and its derivatives are useful for versatile pharmacological applications. To obtain different derivatives of 9H-carbazole, 24 isolates of biphenyl-utilizing bacteria have been investigated regarding their ability to produce hydroxylated 9H-carbazole metabolites. Our analyses showed that 9H-carbazole was primarily converted into 9H-carbazol-1-ol (15 strains) and 9H-carbazol-3-ol (9 strains), while carbazol-9-ol was formed as a minor product (12 strains). The formation of 9H-carbazol-3-ol by the spontaneous release from the corresponding dihydrodiols was provided by the first-time detection of 3-hydroxy-1,2,3,9-tetrahydrocarbazol-4-one. The dependence of product yields on different parameters was exemplarily analyzed for Ralstonia sp. SBUG 290. Biphenyl-grown cells showed higher oxidation activities than cells cultivated with organic acids or nutrient broth, while co-cultivation of Ralstonia sp. SBUG 290 with biphenyl and 9H-carbazole led to an enhanced yield of 9H-carbazol-1-ol. The tested bacterial strains were also studied regarding their biotransformation of the two structure-related compounds 9H-fluorene and dibenzothiophene. Twenty-one strains primarily transformed 9H-fluorene into 9H-fluoren-9-ol and fluoren-9-one. Three strains accumulated benzo[c]chromen-6-one as a novel dead-end product during the incubation with 9H-fluorene, 9H-fluoren-9-ol, and fluoren-9-one. Dibenzothiophene has been mainly transformed into the dead-end product dibenzothiophene-5-oxide, while additional metabolites indicated that the transformation followed the so called Kodama pathway.

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Acknowledgments

This study was supported by the scholarship program of the German Federal Environmental Foundation (DBU). We thank M. Lalk, Institute of Pharmacy, University of Greifswald for the recording of NMR spectra.

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  1. Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Straße 15, 17487, Greifswald, Germany

    Doreen Waldau, Annett Mikolasch & Frieder Schauer

  2. Institute of Pharmacy, Ernst-Moritz-Arndt-University of Greifswald, Greifswald, Germany

    Karen Methling

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  1. Doreen Waldau
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Correspondence to Doreen Waldau.

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Waldau, D., Methling, K., Mikolasch, A. et al. Characterization of new oxidation products of 9H-carbazole and structure related compounds by biphenyl-utilizing bacteria. Appl Microbiol Biotechnol 81, 1023–1031 (2009). https://doi.org/10.1007/s00253-008-1723-8

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