5-hydroxyquinoline-2-carboxylic Acid, a dead-end metabolite from the bacterial oxidation of 5-aminonaphthalene-2-sulfonic Acid.
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.
Nörtemann
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B
Technische Chemie und Chemische Verfahrenstechnik, Universität-GH Paderborn, 4790 Paderborn, Institut für Organische Chemie, Universität Göttingen, 34 Göttingen, and Institut für Mikrobiologie der Universität Stuttgart, Azenbergstrasse 18, 7 Stuttgart 1, Germany.
Glässer
A
A
Machinek
R
R
Remberg
G
G
Knackmuss
H J
HJ