3-Methylquinoline Pathway Map

3-Methhylquinoline can be found in groundwater near landfills containing azaarene contaminated wastes, near creosote wood preservation facilities, in aquifers affected by fossil fuel processing activities and in shale oil. This compound is a known carcinogen causing various health effects and environmental damage, thus its environmental fate and biodegradation is important (Schach et al., 1993).

Comamonas testosteroni 63, from activated sludge, is known to degrade 3-methylquinoline to 2,5,6-trihydroxy-3-methylpyridine. This compound is degraded further to unknown products (Schach et al., 1993). Quinoline, the unsubstituted derivative of 3-methylquinoline, is degraded by Rhodococcus strain B1 in a similar manner to form 5-hydroxy-6-(3-carboxyoxopropenyl)-1H-2-pyridone, which is further degraded to unknown metabolites (Schwarz et al., 1989).

The following is a text-format 3-methylquinoline pathway map. An organism which can initiate the pathway is given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (15k) format.

                                3-Methylquinoline
                            Comamonas testosteroni 63
                                      |
                                      |
                                      | quinoline 2-oxidoreductase
                                      |
                                      |
                                      v
                        3-Methyl-2-oxo-1,2-dihydroquinoline
                              /                   \
                             /                     \
        3-methyl-2-oxo-1,2- /                       \ 2-oxo-1,2-dihydroquinoline
          dihydroquinoline /                         \ 5,6-dioxygenase
          6-monooxygenase /                           \
                         /                             \
                        /                               \
          6-Hydroxy-3-methyl-                  cis-5,6-Dihydrodiol-3-methyl-
       2-oxo-1,2-dihydroquinoline                2-oxo-1,2-dihydroquinoline
                         \                             /
6-hydroxy-3-methyl-2-oxo- \                           / 5,6-dihydrodiol-3-methyl-
      1,2-dihydroquinoline \                         / 2-oxo-1,2-dihydroquinoline
            5-monooxygenase \                       / dehydrogenase
                             \                     /
                              \                   /
                5,6-Dihydroxy-3-methyl-2-oxo-1,2-dihydroquinoline
                                       |
                                       |
                                       | 5,6-dihydroxy-3-methyl-
                                       | 2-oxo-1,2-dihydroquinoline
                                       | dioxygenase
                                       |
                                       v
           3-Methyl-5-hydroxy-6-(3-carboxy-3-oxopropenyl)-1H-2-pyridone
                                       |
                                       |
                                       | 3-methyl-5-hydroxy-6-
                                       | (3-carboxy-3-oxopropenyl)-1H-2-
                                       | pyridone hydratase aldolase
                                       |
                                       v
                        2,5,6-Trihydroxy-3-methylpyridine

Page Author(s): Sandy Etienne

© 2024, EAWAG. All rights reserved.

http://eawag-bbd.ethz.ch/mqn/mqn_map.html