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Microbial Degradation of RDX and HMX SERDP Project CU1213

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Microbial Degradation of RDX and HMX SERDP Project CU1213 Microbial Degradation of RDX and HMX SERDP Project CU1213 Performing Organizations Biotechnology Research Institute, National Research Council of Canada, 6100 Royalmount Ave., Montreal (Quebec) H4P 2R2, Canada. Defense Research and Development Canada, Valcartier (Quebec) G3J 1X5, Canada US Air Force Research Laboratory, 139 Barnes Dr, Tyndall AFB, Fl 32403 Final Report (December 2001 - December 2003) Submitted to Andrea Leeson, 901 North Stuart St., Suite 303 Arlington, Virginia, 22203 February 2004 Project Participants BRI, Canada: Jalal Hawari, Ph.D. Chemistry, PI Jian-Shen Zhao, Ph.D. Microbiology Bharat Bhushan, Ph.D. Biochemistry Vimal Balakrishnan, Ph.D. Chemistry Diane Fournier, Ph.D. Microbiology Annamaria Halasz, M.Sc. Analytical Chemistry Carl Groom, M.Sc. Eng. Chemical Engineering Tara Hooper, B.Sc. Biochemistry Louise Paquet, B.Sc. Chemistry AFRL, USA: Jim Spain, Ph.D. Biochemistry, Co-PI Sandra Trott, Ph.D. Microbiology DRDC, Canada Guy Ampleman, Ph.D. Chemistry Sonia Thiboutot, Ph.D. Chemistry 2 TABLE OF CONTENTS TABLE OF CONTENTS .................................................................................................................................... 3 I PROJECT BACKGROUND..................................................................................................................... 6 II GLOBAL OBJECTIVES .......................................................................................................................... 9 III SUMMARY OF ACCOMPLISHMENTS ............................................................................................. 10 IV TECHNICAL APPROACH .................................................................................................................... 11 IV.1 CHEMICALS AND REAGENTS. ............................................................................................................. 12 IV.2 SYNTHESIS OF METHYLENEDINITRAMINE (MEDINA)....................................................................... 12 IV.3 SYNTHESIS OF 4-NITRO-2,4-DIAZABUTANAL (NDAB). ...................................................................... 13 IV.4 ENZYMES AND INHIBITORS. ............................................................................................................... 14 IV.5 ANAEROBIC SLUDGE.......................................................................................................................... 14 IV.6 AEROBIC DEGRADERS........................................................................................................................ 14 IV.7 SOIL AND ISOLATES. .......................................................................................................................... 15 IV.8 BIOTRANSFORMATION AND MINERALIZATION OF RDX AND HMX WITH ANAEROBIC SLUDGE: IDENTIFICATION OF INITIAL INTERMEDIATES AND PRODUCTS............................................................................ 15 IV.8.1 Biotransformation of RDX and HMX...................................................................................... 15 IV.8.2 Formation and decomposition of methylenedinitramine, a suspected RDX ring cleavage product. 17 IV.8.3 Analysis of RDX and HMX and their intermediate products. ................................................. 17 IV.9 BIOTRANSFORMATION AND MINERALIZATION OF RDX AND HMX BY RHODOCOCCUS SP. STRAIN DN22: IDENTIFICATION OF INITIAL INTERMEDIATES AND PRODUCTS. ............................................................... 20 IV.9.1 Microbial culture and growth conditions. .............................................................................. 20 IV.9.2 Determination of products. ..................................................................................................... 21 IV.9.3 Production and isolation of RDX dead end product C2H5N3O3 using strain DN22. .............. 22 IV.9.4 Kinetics and stoichiometry of degradation. ............................................................................ 23 IV.10 SCREENING, IDENTIFICATION AND ISOLATION OF DEGRADERS FROM ANAEROBIC SLUDGE. ................ 23 IV.10.1 Isolation and characterization of Klebsiella pneumoniae sp. strain SCZ-1. .......................... 23 IV.10.2 Isolation and characterization of Clostridium sp. Strain HAW-1........................................... 25 IV.11 SCREENING AND IDENTIFICATION OF COMMERCIAL ENZYMES FOR THEIR ABILITY TO DEGRADE RDX AND HMX: INSIGHT INTO INITIAL REACTIONS INVOLVED IN THE DEGRADATION............................................... 27 IV.11.1 Nitrate reductase enzymatic assay. ......................................................................................... 27 IV.11.2 Diaphorase enzymatic assays. ................................................................................................ 28 IV.11.3 Cytochrome P450 Enzymatic assays....................................................................................... 30 IV.12 IDENTIFICATION OF INTERMEDIATE AND END PRODUCTS DURING ALKALINE HYDROLYSIS OF RDX: INSIGHT INTO BIODEGRADATION PATHWAYS. ................................................................................................... 32 IV.13 IDENTIFICATION OF INTERMEDIATES DURING PHOTOLYSIS OF RDX IN AQUEOUS SOLUTIONS AT 350 NM: INSIGHT INTO BIODEGRADATION PATHWAYS. ............................................................................................ 34 IV.14 BIODEGRADATION OF RDX AND HMX IN SOIL UNDER ANAEROBIC CONDITIONS ............................. 35 V PROJECT ACCOMPLISHMENTS....................................................................................................... 37 V.1 BIODEGRADATION OF RDX AND HMX WITH ANAEROBIC SLUDGE: DISCOVERY OF METHYLENEDINITRAMINE. “ THE REMOVAL OF THE FIRST BOTTLENECK IN THE UNDERSTANDING OF THE DEGRADATION PATHWAYS OF RDX AND HMX”.............................................................................................. 38 V.1.1 Biodegradation of RDX and HMX with anaerobic sludge: discovery of methylenedinitramine. 39 V.1.2 Biotransformation of Octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) by Municipal 3 Anaerobic Sludge....................................................................................................................................... 48 V.2 IDENTIFICATION OF BACTERIAL ISOLATES FROM SLUDGE AND THE ENZYMES THAT INITIATE DEGRADATION. ................................................................................................................................................ 57 V.2.1 Klebsiella pneumoniae Strain SCZ-1: Biodegradation of RDX through denitration or reduction to MNX followed by denitration................................................................................................................. 58 V.2.2 Clostridium bifermentans HAW-1: Metabolism of RDX through initial reduction to MNX followed by denitration. ............................................................................................................................. 66 V.2.3 Phylogenetic and metabolic diversity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)- transforming bacteria in strictly anaerobic mixed cultures enriched on RDX as nitrogen source............ 77 V.3 ROLE OF ENZYMES IN THE DEGRADATION OF RDX AND HMX. ........................................................ 89 V.3.1 Biotransformation of RDX Catalyzed by a NAD(P)H: Nitrate Oxidoreductase from Aspergillus niger. 90 V.3.2 Mechanism of xanthine oxidase catalyzed biotransformation of HMX under anaerobic conditions................................................................................................................................................... 99 V.3.3 Diaphorase catalyzed biotransformation of RDX via N-denitration mechanism. ..................... 111 V.4 BIODEGRADATION OF RDX AND HMX UNDER AEROBIC CONDITIONS. ............................................ 121 V.4.1 Biotransformation of RDX with Rhodococcus sp. DN22: discovery of 4-nitro-2,4-diazabutanal and the removal of a second bottleneck in the degradation pathways of cyclic nitramines. ................... 122 V.4.2 Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by a rabbit liver cytochrome P450: Insight into the mechanism of RDX biodegradation by Rhodococcus sp. DN22. ......................... 135 V.5 ABIOTIC DEGRADATION OF RDX AND HMX: PHOTOLYSIS AND HYDROLYSIS.................................. 141 V.5.1 Photodegradation of RDX in aqueous solution: a mechanistic probe for biodegradation with Rhodococcus sp........................................................................................................................................ 142 V.5.2 Hydrolysis of RDX and HMX: bimolecular elimination of HNO2 followed by ring cleavage and decomposition. ......................................................................................................................................... 155 V.6 BIODEGRADATION OF RDX AND HMX IN SOIL................................................................................ 167 V.6.1 The Fate of the Cyclic Nitramine Explosives RDX and HMX in Natural Soil.......................... 168 V.6.2 Anaerobic Degradation of RDX and HMX in Soil by Indigenous Bacteria. ............................. 185 V.6.3 Biodegradation of the RDX Ring Cleavage Product 4-Nitro-2,4-Diazabutanal (NDAB) by Phanerochaete chrysosporium. ................................................................................................................. 189 VI APPENDIX 1: OUTPUTS....................................................................................................................
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