Open AccessTransformation of 2‐chloroquinoline to 2‐chloro‐ cis ‐7,8‐dihydro‐7,8‐dihydroxyquinoline by quinoline‐grown resting cells of Pseudomonas putida 86
Author(s) -
Fetzner Susanne,
Vogler Bernhard,
Lingens Franz
Publication year - 1993
Publication title -
fems microbiology letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.899
H-Index - 151
eISSN - 1574-6968
pISSN - 0378-1097
DOI - 10.1111/j.1574-6968.1993.tb06441.x
Subject(s) - quinoline , pseudomonas putida , metabolite , strain (injury) , chemistry , catabolism , pseudomonas , stereochemistry , biosynthesis , enzyme , transformation (genetics) , chloramphenicol , biochemistry , bacteria , biology , organic chemistry , antibiotics , gene , genetics , anatomy
Resting cells of Pseudononas 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 1 H ‐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 1 H ‐2‐oxoquinoline.