Vanillin Pathway Map

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This pathway was contributed by Yoav Dori, Dong Jun Oh and Stephen Stephens, University of Minnesota.

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

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Page Author(s): Yoav Dori, Dong Jun Oh, Stephen Stephens and Michael Turnbull

June 30, 2014 Contact Us

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