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. 1993 Jun;59(6):1898–1903. doi: 10.1128/aem.59.6.1898-1903.1993

5-Hydroxyquinoline-2-Carboxylic Acid, a Dead-End Metabolite from the Bacterial Oxidation of 5-Aminonaphthalene-2-Sulfonic Acid

Bernd Nörtemann 1, Andrea Glässer 1, Reinhard Machinek 1, Gerd Remberg 1, Hans-Joachim Knackmuss 1,*
PMCID: PMC182178  PMID: 16348967

Abstract

5-Aminonaphthalene-2-sulfonate (5A2NS) is converted by strain BN6 into 5-hydroxyquinoline-2-carboxylate (5H2QC). The authenticity of this new compound is confirmed by nuclear magnetic resonance and mass spectrometry. Its formation is explained by a spontaneous cyclization of the hypothetical metabolite 6′-amino-2′-hydroxybenzalpyruvate. The formation of 5H2QC as a dead-end product of 5A2NS prevents NADH regeneration so that 5A2NS oxidation is limited by the internal NADH pool.

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Selected References

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