title: 5-hydroxyquinoline-2-carboxylic Acid, a dead-end metabolite from the bacterial oxidation of 5-aminonaphthalene-2-sulfonic Acid.
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.
authors.affiliation: 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.
authors.forename: B
authors.initials: B
authors.lastname: Nörtemann
authors.forename: A
authors.initials: A
authors.lastname: Glässer
authors.forename: R
authors.initials: R
authors.lastname: Machinek
authors.forename: G
authors.initials: G
authors.lastname: Remberg
authors.forename: H J
authors.initials: HJ
authors.lastname: Knackmuss