Pyrene Pathway Map

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This pathway was contributed by Nathaniel Keith, University of Minnesota BioC/MicE 5309.

Pyrene is a four-ringed polycyclic aromatic hydrocarbon (PAH). Although not a carcinogen, pyrene is a byproduct of the manufactured gas process and other incomplete combustion processes. Pyrene is present at thousands of sites throughout the United States and pyrene has been shown to be involved in the bacterial cometabolism of the potent carcinogen benzo[a]pyrene (Boonchan et al., 2000), whose metabolism is shown elsewhere on this site. The biodegradation of benzo[a]pyrene is known to proceed through substituted pyrene intermediates (e.g., Schneider et al., 1996). Pyrene can be biodegraded by bacteria and fungi through initial dioxygenase (bacteria) and monooxygenase (bacteria and fungi) reactions.

The following is a text-format Pyrene pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions.

        Graphical Map (15k)                                   Graphical Map (21k)
|------------------------------| |---------------------------------------------------------------------|

           Pyrene                            Pyrene                        Pyrene
  Mycobacterium flavescens            Mycobacterium sp. AP1        Aspergillus niger SK 9317 
 Mycobacterium spp. AP1, KR2,    Mycobacterium vanbaalenii PYR-1  Penicillium glabrum TW 9424 
      6PY1 and RJGII-135               Pleurotus ostreatus          Cunninghamella elegans
Mycobacterium vanbaalenii PYR-1                 |                    Trametes versicolor
    Pseudomonas stutzeri P16                    |                         and others            
      Bacillus cereus P21                       |                             |
          and others                            |                             |
              |                                 | pyrene 4,5-                 | pyrene 1,2-
              |                                 | monooxygenase               | monooxygenase
              | pyrene                          |                             |
              | dioxygenase                     v                             v
              |                          Pyrene-4,5-oxide             Pyrene-1,2-oxide
              v                                 |                     |              |
     cis-4,5-Dihydroxy-                         |                     |              |
     4,5-dihydropyrene                          |                     |              | rapid
              |                                 | pyrene-4,5-         |              | isomerization
              |                                 | epoxide             |              | (non-
              |                                 | hydrolase           |              | enzymatic)
              |                                 |                     |              |
              | 1,2-dihydroxy-                  |                     |              v
              | 1,2-dihydro-                    v                     |       2-Hydroxypyrene
              | naphthalene            trans-4,5-Dihydroxy-           |
              | dehydrogenase           4,5-dihydropyrene             | rapid
              |                                                       | isomerization
              |                                                       | (non-
              |                                                       | enzymatic)
              v                                                       | 
         4,5-Dihydroxy- --------------->Pyrene-4,5-dione              |
           pyrene        autooxidation                                |
              |         (non-enzymatic)                               v
              |                             +--------------- 1-Hydroxypyrene ----------------+
              |                             |                |               |               |
              | 4,5-dihydroxy-              |                |               |               | 
              | pyrene                      | 1-hydroxy-     | 1-hydroxy-    | 1-hydroxy-    | 1-hydroxy-
              | dioxygenase                 | pyrene         | pyrene        | pyrene        | pyrene
              |                             | 6,7-mono-      | 7,8-mono-     | methyl        | sulfo-
              |                             | oxygenase      | oxygenase     | transferase   | transferase
              |                             |                |               |               |
              |                             v                v               v               v 
              v                        1-Hydroxy-       1-Hydroxy-      1-Methoxy-       1-Pyrenyl-
        Phenanthrene-                    pyrene-          pyrene-         pyrene          sulfate
      4,5-dicarboxylate                 6,7-oxide        7,8-oxide           |
              |                             |                |               |
              |                             | rapid          | rapid         | [1-methoxy-
              | phenanthrene-               | isomerization  | isomerization | pyrene
              | 4,5-dicarboxylate           | (non-          | (non-         | 6,7-mono-
              | decarboxylase               | enzymatic)     | enzymatic)    | oxygenase]
              |                             |                |               |
              v                             v                v               v
        Phenanthrene-                1,6-Dihydroxy-    1,8-Dihydroxy-   [1-Methoxy-
        4-carboxylate                    pyrene           pyrene           pyrene-
              |                             |                |           6,7-oxide]
              |                             | auto-          | auto-         |
              | phenanthrene                | oxidation      | oxidation     | [rapid
              | 4-carboxylate               | (non-          | (non-         | isomerization
              | dioxygenase                 | enzymatic)     | enzymatic)    | (non-
              |                             |                |               | enzymatic)]
              v                             v                v               v
    cis-3,4-Phenanthrene                 Pyrene-          Pyrene-      [1-Hydroxy-
        dihydrodiol-                    1,6-dione        1,8-dione    6-methoxypyrene]
        4-carboxylate                                                        |        
              |                                                              |
              | cis-3,4-phenanthrene                                         | [1-hydroxy-
              | dihydrodiol-                                                 | 6-methoxy-
              | 4-carboxylate                                                | pyrene methyl
              | dehydrogenase                                                | transferase]
              |                                                              | 
              v                                                              v
        3,4-Dihydroxy-                                                1,6-Dimethoxy-
         phenanthrene                                                     pyrene
              |
              |
              |
              |
              v
   to the Phenanthrene Pathway

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Page Author(s): Nathaniel Keith

July 11, 2017 Contact Us

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