Literature DB >> 16348967

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

B Nörtemann1, A Glässer, R Machinek, G Remberg, H J Knackmuss.   

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.

Entities:  

Year:  1993        PMID： 16348967      PMCID： PMC182178          DOI： 10.1128/aem.59.6.1898-1903.1993

Source DB:  PubMed          Journal:  Appl Environ Microbiol        ISSN： 0099-2240            Impact factor:   4.792


  12 in total

1.  [CAROTENOIDS IN THIORHODACEAE. I. OKENONEAS THE PRINCIPAL CAROTENOID IN CHROMATIUM OKENII PERTY].

Authors:  K SCHMIDT; S LIAAENJENSEN; H G SCHLEGEL
Journal:  Arch Mikrobiol       Date:  1963-08-01

2.  3-Hydroxyanthranilic acid, a carcinogen produced by endogenous metabolism.

Authors:  E BOYLAND; G WATSON
Journal:  Nature       Date:  1956-05-05       Impact factor: 49.962

3.  Catabolism of Naphthalenesulfonic Acids by Pseudomonas sp. A3 and Pseudomonas sp. C22.

Authors:  C Brilon; W Beckmann; H J Knackmuss
Journal:  Appl Environ Microbiol       Date:  1981-07       Impact factor: 4.792

4.  Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids.

Authors:  A E Kuhm; A Stolz; K L Ngai; H J Knackmuss
Journal:  J Bacteriol       Date:  1991-06       Impact factor: 3.490

5.  Cloning, nucleotide sequence and characterization of genes encoding naphthalene dioxygenase of Pseudomonas putida strain NCIB9816.

Authors:  S Kurkela; H Lehväslaiho; E T Palva; T H Teeri
Journal:  Gene       Date:  1988-12-20       Impact factor: 3.688

6.  The configuration of the 1,2-dihydroxy-1,2-dihydronaphthalene formed in the bacterial metabolism of naphthalene.

Authors:  F A Catterall; K Murray; P A Williams
Journal:  Biochim Biophys Acta       Date:  1971-05-18

7.  Initial reactions in the oxidation of naphthalene by Pseudomonas putida.

Authors:  A M Jeffrey; H J Yeh; D M Jerina; T R Patel; J F Davey; D T Gibson
Journal:  Biochemistry       Date:  1975-02-11       Impact factor: 3.162

8.  Bacterial communities degrading amino- and hydroxynaphthalene-2-sulfonates.

Authors:  B Nörtemann; J Baumgarten; H G Rast; H J Knackmuss
Journal:  Appl Environ Microbiol       Date:  1986-11       Impact factor: 4.792

9.  Naphthalene dioxygenase: purification and properties of a terminal oxygenase component.

Authors:  B D Ensley; D T Gibson
Journal:  J Bacteriol       Date:  1983-08       Impact factor: 3.490

10.  Cancer of the urinary bladder induced in mice with metabolites of aromatic amines and tryptophan.

Authors:  M J ALLEN; E BOYLAND; C E DUKES; E S HORNING; J G WATSON
Journal:  Br J Cancer       Date:  1957-06       Impact factor: 7.640
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  1 in total

1.  Degradation of h-acid by free and immobilized cells of Alcaligenes latus.

Authors:  M S Usha; M K Sanjay; S M Gaddad; C T Shivannavar
Journal:  Braz J Microbiol       Date:  2010-12-01       Impact factor: 2.476
  1 in total

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