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
Page Author(s): Nathaniel Keith
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