FEMS Microbiology Letters 1993-09-01

Transformation of 2-chloroquinoline to 2-chloro-cis-7,8-dihydro-7,8- dihydroxyquinoline by quinoline-grown resting cells of Pseudomonas putida 86.

S Fetzner, B Vogler, F Lingens

Index: FEMS Microbiol. Lett. 112(2) , 151-7, (1993)

Full Text: HTML

Abstract

Resting cells of Pseudomonas putida strain 86 were grown on quinoline transformed 2-chloroquinoline to 2-chloro-cis-7,8-dihydro-7,8-dihydroxyquinoline which was not converted further. 7,8-Dioxygenating activity was present when the enzymes of quinoline catabolism were induced. Quinoline-grown cells of strain 86 treated simultaneously with 2-chloroquinoline and D-(-)-threo-chloramphenicol to prevent protein biosynthesis also formed the cis-7,8-dihydrodiol of 2-chloroquinoline. Succinate-grown resting cells did not oxidize 2-chloroquinoline. Acid-catalyzed decomposition of 2-chloro-cis-7,8-dihydro-7,8-dihydroxyquinoline predominantly yielded 2-chloro-8-hydroxyquinoline. By analogy, accumulation of the putative dead-end metabolite 1H-8-hydroxy-2-oxoquinoline during growth of P. putida 86 on quinoline is suggested to likewise result from dehydration of the 7,8-dihydrodiol of 1H-2-oxoquinoline.

Related Compounds

  • Chloroquinoline

Related Articles:

Antiprotozoal activity of chloroquinoline based chalcones.

2011-05-01

[Eur. J. Med. Chem. 46 , 1897-905, (2011)]

Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: an efficient route to 2-quinolinones.

2014-07-03

[Org. Lett. 16(13) , 3568-71, (2014)]

Chemoenzymatic synthesis of chiral 2,2'-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes.

2010-03-07

[Org. Biomol. Chem. 8(5) , 1081-90, (2010)]

Discovering some novel 7-chloroquinolines carrying a biologically active benzenesulfonamide moiety as a new class of anticancer agents.

2013-01-01

[Chem. Pharm. Bull. 61(1) , 50-8, (2013)]

C-C bond formation at C-2 of a quinoline ring: synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors.

2012-04-01

[Bioorg. Med. Chem. 20(7) , 2199-207, (2012)]

More Articles...