Nitrophenol Family Pathway Map (an/aerobic)

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This pathway was contributed by Hugh McTavish, Jill Kuglin Schweitzer, Dong Jun Oh, Prasad Kotharu and Michael Turnbull, University of Minnesota and Rakesh K. Jain, Ashvini Chauhan and Gunjan Pandey, Institute of Microbial Technology, Chandigarh, India.

Nitroaromatic compounds are recognized as environmentally hazardous and widely used for the industrial production of dyes, pesticides, plasticizers, explosives and solvents. Both oxidative and reductive mechanisms for degradation of nitrophenol compounds have been reported. A Moraxella sp. utilizes 4-nitrophenol as a sole source of carbon and nitrogen via an initial monooxygenase-catalyzed elimination of nitrite (Spain, J.C.; Gibson, D.T., 1991. Pathway for degradation of p-nitrophenol in a Moraxella sp. Applied and Environmental Microbiology. 57: 812-819; S. Nishino, personal communication, 2003). Similar monooxygenase reactions in Arthrobacter sp. strain JS443 and Arthrobacter protophormiae RKJ100 remove nitrite from 4-nitrophenol or 4-nitrocatechol in preparation for ring cleavage (Jain et al., 1994; Chauhan et al., 2000). Pseudomonas putida B2 and Alcaligenes sp. NyZ215 also employ a monooxygenase for the removal of nitrite from 2-nitrophenol to produce the ring cleavage substrate, catechol (Zeyer et al., 1986 and Xiao et al., 2007).

Under aneraobic conditions, Ralstonia eutropha JMP 134 and Pseudomonas putida B2 initially reduce the nitro group of 3-nitrophenol to form the hydroxylamino derivative. A mutase reaction, similar to the acid-catalyzed Bamberger rearrangement, converts 3-hydroxyaminophenol to aminohydroquinone (Schenzle et al., 1999) or 4-aminocatechol (Zhao et al., 2000). Meulenberg et al. (1996) reported the formation of 1,2,4-benzenetriol, which is proposed to form via a monooxygenase-type oxidation and elimination of ammonia.

Resorcinol is used in the manufacture of adhesives and dyes and as an ingredient in pharmaceutical preparations for the topical treatment of skin conditions. Phenol 2-monooxygenase hydroxylates resorcinol by reducing flavin with molecular oxygen.

The following is a text-format 4-nitrophenol degradation 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 format.

                                              Graphical Map (15k)                            |                     Graphical Map (6k)

                             from the
                      Parathion and Nitrofen
                  +--------- Pathways --------------------------------> 4-Nitrophenol                  3-Nitrophenol                 2-Nitrophenol
                  |             |                                Arthrobacter protophormiae      Ralstonia eutropha JMP 134      Pseudomonas putida B2
                  |             |                                          RKJ100                  Pseudomonas putida B2         Alcaligenes sp. NyZ215
                  |             |                                   Arthrobacter sp. JS443                   |                             |
                  |             v                                             |                              |                             | 2-nitrophenol
   from the       |       4-Nitrophenol                                       | 4-nitrophenol                | 3-nitrophenol               | 2-monooxygenase
  Bisphenol A,    |       Moraxella sp.                                       | 2-monooxygenase              | nitroreductase              |
  Bisphenol F,    |             |                                             |                              |                             |
 4-Nonylphenol,   |             | 4-nitrophenol                               v                              v                             v
  4-Hydroxy-      |             | 4-monooxygenase                      4-Nitrocatechol             3-Hydroxylaminophenol                Catechol
 acetophenone,    |             |                                             |                              |                             |
 gamma-Lindane    |             |                                             | 4-nitrocatechol    +---------+---------+                   | 
 and Vanillin     |             |   2-Hydroxy-1,4-benzoquinone <--------------+ 4-monooxygenase    |                   |                   |
   Pathways       |             |     |                  | ^                                       | 3-hydroxyl-       | 3-hydroxyl-       v
      |           |             |     | 2-hydroxy-1,4-   | |                                       | aminophenol       | aminophenol     to the         
      |           +------------>|     | benzoquinone     | |                                       | mutase            | mutase       Nitrobenzene
      |                         |     | 2-reductase      | |                                       |                   |                Pathway
      |                         |     |                  | |                                       v                   v
      |                         |     |                  | |                               Aminohydroquinone    4-Aminocatechol
      |                         |     |         hydroxy- | |                                       |                   |
      |                         v     v     benzoquinone | |                                       |                   | 
      |           +-------- p-Benzoquinone     reductase | | 1,2,4-              aminohydroquinone v                   v 4-aminocatechol
      |           |                                      | | benzenetriol                  oxidase |                   | oxidase
      |           | p-benzoquinone                       | | dehydrogenase                         |                   |    
      |           | reductase                            | |                                       +---------+---------+
      |           |                hydroquinone          | |                                                 |                         
      |           v                hydroxylase           v |                                                 |                           
      +---> Hydroquinone -----------------------------> 1,2,4-benzenetriol <---------------------------------+
         C. parapsilosis CBS604                               |        ^
                  |                                           |        | phenol
                  | hydroquinone                              |        | 2-mono-
                  | 1,2-dioxygenase                           |        | oxygenase
                  |                                           |        |
                  V                                           |    Resorcinol
       cis,cis-4-Hydroxymuconic                               |
             semialdehyde                                     |
                  |                                           |
                  | 4-hydroxymuconic                          | 1,2,4-
                  | semialdehyde                              | benzenetriol
                  | dehydrogenase                             | dioxygenase
                  v                                           |
            Maleylacetate <-----------------------------------+
                  |
                  | maleylacetate
                  | reductase
                  |
                  v
            3-Oxoadipate
                  |
                  | 3-oxoadipate
                  | CoA-transferase
                  |
                  v
           3-Oxoadipyl-CoA  <------ from the Cyclohexane Pathway
                  |
                  | acetyl-CoA
                  | C-acyltransferase
                  |
                  v
     Acetyl-CoA  + Succinyl-CoA
         |               |
         |               |
         |               |
         v               v
   Intermediary    Intermediary
    Metabolism      Metabolism
      (KEGG)          (KEGG)

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Page Author(s): Hugh McTavish, Gunjan Pandey, Prasad Kotharu and Michael Turnbull

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