5-HYDROXYQUINOLINE-2-CARBOXYLIC ACID, A DEAD-END METABOLITE FROM THE BACTERIAL OXIDATION OF 5-AMINONAPHTHALENE-2-SULFONIC ACID

Authors
NORTEMANN B GLASSER A MACHINEK R REMBERG G KNACKMUSS HJ
Citation
B. Nortemann et al., 5-HYDROXYQUINOLINE-2-CARBOXYLIC ACID, A DEAD-END METABOLITE FROM THE BACTERIAL OXIDATION OF 5-AMINONAPHTHALENE-2-SULFONIC ACID, Applied and environmental microbiology, 59(6), 1993, pp. 1898-1903
Citations number
18
Categorie Soggetti
Microbiology,"Biothechnology & Applied Migrobiology
Journal title
Applied and environmental microbiology → ACNP
ISSN journal
00992240
Volume
59
Issue
6
Year of publication
1993
Pages
1898 - 1903
Database
ISI
SICI code
0099-2240(1993)59:6<1898:5AADMF>2.0.ZU;2-M
Abstract
5-Aminonaphthalene-2-sulfonate (5A2NS) is converted by strain BN6 into 5-hydroxyquinoline-2-carboxylate (5H2QC). The authenticity of this ne w compound is confirmed by nuclear magnetic resonance and mass spectro metry. Its formation is explained by a spontaneous cyclization of the hypothetical metabolite 6'-amino-2'-hydroxybenzalpyruvate. The formati on of 5H2QC as a dead-end product of 5A2NS prevents NADH regeneration so that 5A2NS oxidation is limited by the internal NADH pool.