o-Nitrobenzoate Pathway Map

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This pathway was contributed by Yoshie Hasegawa, Kansai University, Osaka, Japan, and Rakesh K Jain and Ashvini Chauhan, Institute of Microbial Technology, Chandigarh, India, completed by Prasad Kotharu and Lynda Ellis, University of Minnesota, and up-dated by Carla Essenberg, University of Minnesota.

o-Nitrobenzoate is used as a reagent for protection of NH2 groups in organic synthesis. Pseudomonas fluorescens KU-7, Arthrobacter protophormiae RKJ100, and other strains are capable of utilizing o-nitrobenzoate as the sole carbon, nitrogen and energy source (Hasegawa et al., 2000; Chauhn et al., 2000; Muraki et al., 2003). o-Nitrobenzoate is degraded by a two electron reduction of the nitro moiety, yielding o-Hydroxylaminobenzoate. Ps. fluorescens KU-7 (Hasegawa et al., 2000), and more recently A. protophormiae RKJ100 (Pandey et al., 2003), were shown to transform o-Hydroxylaminobenzoate to 3-Hydroxyanthranilate. In addition, A. protophormiae RKJ100 can transform it to 2-Aminobenzoate (anthranilic acid). This oxygen-insensitive reductive catabolic pathway of o-nitrobenzoate provides evidence that 2-Aminobenzoate is not produced as a side reaction but is an obligate intermediate in a direct energy yielding metabolic pathway by Arthrobacter protophormiae RKJ100 (Chauhan et al., 2000).

The following is a text-format o-nitrobenzoate pathway map. An organism which can initiate the pathway is 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 (10k) format.

                                        o-Nitrobenzoate
                                    Pseudomonas fluorescens KU-7
                                 Arthrobacter protophormiae RKJ100
                                               |
                                               | o-nitrobenzoate
                                               | nitroreductase
                                               v
                                               |
                                               v
                                  +-o-Hydroxylaminobenzoate-+
                       (only A. protophormiae)              |
                                  |                         |
          o-hydroxylaminobenzoate |                         | o-hydroxylaminobenzoate
                   nitroreductase |                         | mutase
                                  |                         |
                                  |                         |
                                  v                         v
                          2-Aminobenzoate         3-Hydroxyanthranilate       
                                  |                         |
                                  |                         | 3-hydroxyanthranilate
                                  |                         | 3,4-dioxygenase        
                                  |                         |
                                  v                         v
                                to the          2-Amino-3-carboxymuconate- 
                           2-Aminobenzoate            6-semialdehyde
                               Pathway                      | 
                                                            |
                                                            |
                                                            v
                                                       Intermediary
                                                        Metabolism
                                                          (KEGG)

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Page Author(s): Prasad Kotharu and Lynda Ellis

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