Hexahydro-1,3,5-Trinitro-1,3,5-Triazine Pathway Map

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This pathway was contributed by Jeff Roberts, BioC/MicE 5309, and Prasad Kotharu and Sean Anderson, University of Minnesota.

Hexahydro-1,3,5-trinitro-1,3,5-triazine, commonly known as RDX (Royal Demolition eXplosive), is a reduced symmetrical triazine ring compound rendered explosively unstable by the three N-nitro substituents. RDX is a synthetic product that does not occur naturally in the environment. RDX is also known as cyclonite and hexagen. RDX can enter the environment through the manufacturing process or improper handling and disposal methods. Alternatively, RDX can contaminate water and soil from spills or leaks at hazardous waste disposal sites. Airborne contamination of RDX occurs when it is disposed of by burning.

RDX is degraded both aerobically and anaerobically by microorganisms. Rhodococcous sp. strain DN22 degrades RDX aerobically, with accumulation of 4-Nitro-2,4-diazabutanal, a dead-end product. Compounds in brackets are postulated but have not been isolated (Bhushan et al., 2003).

The ring cleavage product 4-nitro-2,4-diazabutanal is mineralized to nitrate and carbon dioxide in Methylobacterium sp. JS178 (Fournier et al., 2005) and Phanerochaete chrysosporium (Fournier et al., 2004).

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

                Hexahydro-1,3,5-trinitro-1,3,5-triazine
                      Rhodococcus sp. strain DN22
                                   |
                                   | unspecific
                                   | monooxygenase
                                   | 
                                   |
                                   v
            [1,3-Dinitro-1,2,3,4-tetrahydro-1,3,5-triazine]
                                   |
                                   | unspecific
                                   | monooxygenase
                                   |
                                   v
                  [1-Nitro-1,2-dihydro-1,3,5-triazine]
                                   |
                                   | 1-nitro-1,2-
                                   | dihydro-1,3,5-
                                   | triazine hydrolase
                                   v
                  [1-Nitro-1,3,5-triazinane-2,4-diol]
                                   |
                                   |  
                                   v A                       
                                   |                        
                                   |   
                                   v  
                       4-Nitro-2,4-diazabutanal + [Formamide]   
                                   |                   |
                                   |                   | formamide hydrolase
                                   |                   |
                                   |                   v
                                   v B              Formate
                                   |                   |
                                   |                   | formate
                                   |                   | dehydrogenase
                                   |                   |
                                   +---------+---------+
                                             |
                                             v
                                      Carbon dioxide

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Page Author(s): Jeff Roberts, Prasad Kotharu and Sean Anderson

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