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16348967
5-hydroxyquinoline-2-carboxylic Acid, a dead-end metabolite from the bacterial oxidation of 5-aminonaphthalene-2-sulfonic Acid.

Appl Environ Microbiol, 1993/6;59(6):1898-903.

Nörtemann B[1], Glässer A, Machinek R, Remberg G, Knackmuss HJ

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PMID: 16348967

Impact factor: 5.005

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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