Biphenyl Pathway Map

 Biphenyl is an aromatic hydrocarbon with some toxicity. A number of bacteria are able to initiate the degradation of the compound by adding molecular oxygen to the ring. Pseudomonia sp. strain LB 400 is particularly noteworthy. It encodes four enzymes and catabolizes biphenyl to benzoate and 2-hydroxypenta-2,4-dienoate through four steps, often called the biphenyl upper pathway. Interestingly, after growth with biphenyl, many bacteria can oxidize polychlorinated biphenyls (PCBs), a group of man-made compounds composed of biphenyl molecules containing from 1 to 10 chlorines, and persistent and toxic in biophere. It has been shown that PCBs follow the same catabolic pathway as biphenyl and use the same enzymes. Biphenyl dioxygenase plays a critical role in PCB degradation by catalyzing the first step. Its activity varies depending on the number of chlorines and their positions on the aromatic ring. The EAWAG-BBD also contains the biodegradation pathway for one model PCB, 4-chlorobiphenyl.

This pathway is a description of the upper pathway for metabolism of biphenyl as encoded by the bph locus of Pseudomonas sp. strain LB400 as described by Seeger, et al. (1995).

The following is a text-format biphenyl 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 (10 k) format.

 
                  Biphenyl
        Pseudomonas sp. strain LB400  
                     |
                     |
                     | biphenyl
                     | 2,3-dioxygenase
                     |
                     |                
                     v                   
              cis-2,3-Dihydro-    
            2,3-dihydroxybiphenyl 
                     |                                             from the
                     | 2,3-dihydro-2,3-                Dibenzothiophene Desulfurization
                     | dihydroxybiphenyl                            Pathway
                     | dehydrogenase                                   |
                     |                                                 |
                     |                  2-hydroxybiphenyl              |
                     v                   3-monooxygenase               v
           2,3-Dihydroxybiphenyl  <--------------------------- 2-Hydroxybiphenyl                                                                                                  
                     |                                                                                                           
                     | 
                     | 2,3-dihydroxybiphenyl
                     | 1,2-dioxygenase
                     | 
                     |
                     v 
              2-Hydroxy-6-oxo-
          6-phenylhexa-2,4-dienoate 
                     |
                     |
                     | 2-hydroxy-6-oxo-6-
                     | phenylhexa-2,4-dienoate
                     | hydrolase
                     |
                     v 
           Benzoate  +  cis-2-Hydroxypenta-2,4-dienoate 
               |                    | 
               |                    |
               |                    |                                    
               |                    |  
               v                    v                   
             to the               to the 
            Benzoate          4-Chlorobiphenyl
            Pathway               Pathway

Page Author(s): David Linden and Zhifu Sun

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http://eawag-bbd.ethz.ch/bph/bph_map.html