Transformation of 2-chloroquinoline to 2-chloro-cis-7,8-dihydro-7,8- dihydroxyquinoline by quinoline-grown resting cells of Pseudomonas putida 86.
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.
Fetzner
S
S
Institut für Mikrobiologie, Universität Hohenheim, Stuttgart, FRG.
Vogler
B
B
Lingens
F
F
D001711:Biotransformation; D002701:Chloramphenicol / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D006912:Hydroxyquinolines / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D016958:Pseudomonas putida / Q000187:drug effects / Q000254:growth & development / Q000378:metabolism*; D011804:Quinolines / Q000378:metabolism*
D006912:Hydroxyquinolines; D011804:Quinolines; C083775:2-chloro-7,8-dihydro-7,8-dihydroxyquinoline; D002701:Chloramphenicol; C037219:quinoline; C083774:2-chloroquinoline