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), one of the Top 20 Hazardous Substances
on the CERCLA
priority list. Furthermore, 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)
| | | |
| cis-4,5- | | v
| dihydroxy- v | 2-Hydroxypyrene
| 4,5-dihydro- trans-4,5-Dihydroxy- |
| pyrene 4,5-dihydropyrene | rapid
| dehydrogenase | 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
Page Author(s): Nathaniel Keith
April 25, 2008 Contact Us
© 2008, University of Minnesota. All rights reserved. http://umbbd.msi.umn.edu/pyr/pyr_map.html