Alpha-Pinene Pathway Map

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This pathway was contributed by Diana Wong, Shiqian Li and Sean Anderson University of Minnesota.

Alpha-Pinene is a monoterpene that may be a significant factor affecting bacterial activities in nature. It is a major component in tea-tree oils, and gives off a piney smelling odor. Terpenes are widely used as flavorings, deodorants, and medicines (as in the treatment of acne).

It is not clear whether the enzymes from B. pallidus here named "alpha-pinene dehydrogenase" and "alpha-pinene monooxygenase" are the same enzyme or two different enzymes. Indeed, these pathways may be catalyzed by a limited number of isomerase, monooxygenase and dehydrogenase enzymes with broad substrate specificities. Glycine mediates the isomerization of cis-2-Methyl-5-isopropylhexa-2,5-dienoic acid to trans-2-Methyl-5-isopropylhexa-2,5-dienoic acid. The beta-oxidation reactions transforming cis/trans-2-Methyl-5-isopropylhexa-2,5-dienoic acid to 3-Isopropylbut-3-enoic acid are postulated (Savithiry et al., 1998).

The following is a text-format alpha-Pinene 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.

|-----------Graphical Map (12K)---------------------|                       Graphical Map (21K)

          alpha-Pinene                   alpha-Pinene                         alpha-Pinene
          Nocardia sp.                 Pseudomonas putida                  Pseudomonas putida
     Pseudomonas fluorescens                   |                              Nocardia sp.    
                |                              |                                   |         
      +---------------------+                  |                                   |
      |                     |                  |                                   |
      |                     |                  |                                   | 
      |                     |                  |                                   | 
      | alpha-pinene        | alpha-pinene     | alpha-pinene                      | alpha-pinene mono-
      | dehydrogenase       | lyase            | monooxygenase                     | oxygenase[NADH]
      |                     |                  |                                   |
      |                     |                  |                                   |
      V                     V                  |                                   V                   
   Myrtenol              Limonene              |                          alpha-Pinene oxide            
      |                     |                  |                                   | 
      |                     |                  |                                   | 
      |                     |                  |                                   | 
      | myrtenol            | limonene         |                                   | alpha-pinene
      | dehydrogenase       | 6-monooxygenase  |                                   | oxide lyase
      |                     |                  |                      +------------+
      |                     |                  |                      |                              
      V                     V                  V                      V                          
   Myrtenal              Carveol <-------- Pinocarveol       cis-2-Methyl-5-iso-  --> trans-2-Methyl-5-iso-           
      |                     |   pinocarveol    |            propylhexa-2,5-dienal     propylhexa-2,5-dienal 
      |                     |   isomerase      |                      |                         | 
      |                     |                  |                      |                         | 
      | myrtenal            | carveol          | pinocarveol          | cis-2-methyl-5-iso-     | trans-2-methyl-5-iso-                     
      | dehydrogenase       | dehydrogenase    | dehydrogenase        | propylhexa-2,5-dienal   | propylhexa-2,5-dienal 
      |                     |                  |                      | dehydrogenase           | dehydrogenase
      |                     V                  |                      |                         |
      V                  to the                V                      V                         V
 Myrtenic acid      Limonene Pathway      Pinocarvone          cis-2-Methyl-5-          trans-2-Methyl-5-          
                                                              isopropylhexa-2,5-        isopropylhexa-2,5-       
                                                                dienoic acid              dienoic acid 
                                                                      |                         |
                                                                      | cis-2-methyl-5-         | trans-2-methyl-5-          
                                                                      | isopropylhexa-2,5-      | isopropylhexa-2,5-          
                                                                      | dienoate-CoA ligase     | dienoate-CoA ligase          
                                                                      |                         |
                                                                      v                         v 
                                                               cis-2-Methyl-5-          trans-2-Methyl-5-       
                                                              isopropylhexa-2,5-        isopropylhexa-2,5-       
                                                                 dienoyl-CoA               dienoyl-CoA       
                                                                      |                         |
                                                                      | enoyl-CoA hydratase     | enoyl-CoA hydratase          
                                                                      |                         |
                                                                      |                         |
                                                                      +----> 3-Hydroxy-2,6- <---+       
                                                                          dimethyl-5-methylene-       
                                                                            heptanoyl-CoA       
                                                                                   |               
                                                                                   | 3-hydroxy-2,6-dimethyl-                                 
                                                                                   | 5-methylene-heptanoyl-                                 
                                                                                   | CoA dehydrogenase                                 
                                                                                   |               
                                                                                   v             
                                                                             2,6-Dimethyl-5-       
                                                                             methylene-3-oxo- 
                                                                             heptanoyl-CoA
                                                                                   |               
                                                                                   | 2,6-dimethyl-5-methylene-                 
                                                                                   | 3-oxo-heptanoyl-CoA                 
                                                                                   | C-acetyltransferase                 
                                                                                   | 
                                                                                   v
                                                                            3-Isopropylbut- 
                                                                              3-enoyl-CoA               
                                                                                   |               
                                                                                   | 3-isopropylbut-                 
                                                                                   | 3-enoyl CoA                 
                                                                                   | thioesterase                 
                                                                                   | 
                                                                                   v
                                                                            3-Isopropylbut-3               
                                                                              enoic acid  

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Page Author(s): Diana Wong, Shiqian Li, Sean Anderson

July 11, 2017 Contact Us

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