chiniofon and 2-chloroquinoline

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.

Topics: Biotransformation; Chloramphenicol; Hydrogen-Ion Concentration; Hydroxyquinolines; Magnetic Resonance Spectroscopy; Pseudomonas putida; Quinolines