Vanillin, a common flavoring agent, is produced from ground black vanilla bean pods. Vanillin can also be produced from the biodegradation of lignin, a paper manufacturing byproduct and also the second most abundant naturally-occuring biopolymer. Regarding vanilly-alcohol oxidase, Dr. Willem J.H. van Berkel (personal communication, 2001) states, "Vanillyl alcohol is not a growth substrate for the fungus. The enzyme is only induced by growth on veratryl alcohol, anisyl alcohol and 4-(methoxymethyl)phenol. We have found that the latter compound is the only inducer which is converted by the enzyme."
Demethylation of 4-methoxybenzoate is also included in the pathway. 4-Methoxybenzoate monooxygenase O-demethylates 4-methoxybenzoate in the presence of molecular oxygen and of NAD(P)H as electron donor (Bernhardt et al., 1988). This EAWAG-BBD pathway is arbitrarily chosen as a "trunk" pathway, one which funnels the products of other pathways to intermediary metabolism.
The following is a text-format Vanillin 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. This map is also available in graphic (18k) format.
vanillyl-alcohol
oxidase
4-Methoxy- Vanillin <--------------- Vanillyl alcohol
benzoate Arthrobacter sp. Ru61a Penicillium simplicissimum
Pseudomonas |
putida | vanillin
| | dehydrogenase
| 4-methoxy- |
| benzoate |
from the | monooxygenase |
Toluene, Benzoate v v
2,4-Dichlorobenzoate,---> 4-Hydroxybenzoate Vanillate
Bisphenol A and | | |
Bisphenol F Pathways | | |
| | |
4-hydroxylbenzoate | | | vanillate
1-hydroxylase | | | monooxygenase
Hydroquinone <----------+ | | (aerobic) from the
| | 4-hydroxybenzoate | or Permethrin
| | 3-monooxygenase | vanillate Toluene-4-sulfonate,
| | | O-demethylase 4-Carboxy-4'-sulfoazobenzene,
| | | (anaerobic) m-Cresol and
v +---------------------+ | Dimethyl isopthalate Pathways
to the | | |
4-Nitrophenol from the v v |
Pathway Phthalate ------> 3,4-Dihydroxybenzoate <------------------------+
Family (Protocatechuate)
Pathway | | |
| | |
+-------------------+ | +-------------------+
| | |
procatechuate | | procatechuate | protocatachuate
3,4-dioxygenase | | 4,5-dioxygenase | decarboxylase
| | |
v v v
3-Carboxy-cis, 2-Hydroxy-4-carboxymuconate Catechol
cis-muconate semialdehyde |
| | |
| | |
v v v
Intermediary to the to the
Metabolism Syringate Nitrobenzene
(KEGG) Pathway Pathway
Page Author(s): Yoav Dori, Dong Jun Oh, Stephen Stephens and Michael Turnbull
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