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Nitration Enzyme Toolkit for the Biosynthesis of Energetic Materials

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ORNL/SPR-2017/498 Oak Ridge National Laboratory Nitration enzyme toolkit for the biosynthesis of energetic materials PI: David E. Graham SERDP Project Number Jim C. Spain WP-2332 Ronald J. Parry Robert L. Hettich February 5, 2018 Approved for public release. Distribution is unlimited. Form Approved REPORT DOCUMENTATION PAGE OMB No. 0704-0188 Public reporting burden for this collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing this collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden to Department of Defense, Washington Headquarters Services, Directorate for Information Operations and Reports (0704-0188), 1215 Jefferson Davis Highway, Suite 1204, Arlington, VA 22202- 4302. Respondents should be aware that notwithstanding any other provision of law, no person shall be subject to any penalty for failing to comply with a collection of information if it does not display a currently valid OMB control number. PLEASE DO NOT RETURN YOUR FORM TO THE ABOVE ADDRESS. 1. REPORT DATE (DD-MM-YYYY) 2. REPORT TYPE 3. DATES COVERED (From - To) 02-05-2018 Final Report 01-09-2013 to 09-30-2017 4. TITLE AND SUBTITLE 5a. CONTRACT NUMBER WP-2332 Nitration enzyme toolkit for the biosynthesis of energetic materials 5b. GRANT NUMBER 5c. PROGRAM ELEMENT NUMBER 6. AUTHOR(S) 5d. PROJECT NUMBER Graham, David E; Spain, Jim C; Parry, Ronald J; Hettich, Robert L; Mahan, Kristina M; 5e. TASK NUMBER Klingeman, Dawn M; Giannone, Richard J; Gulvick, Christopher A; Fida, Tekle T 5f. WORK UNIT NUMBER 7. PERFORMING ORGANIZATION NAME(S) AND ADDRESS(ES) 8. PERFORMING ORGANIZATION REPORT Oak Ridge National Laboratory NUMBER PO Box 2008, MS-6038 Oak Ridge, TN 37831 ORNL/SPR-2017/498 9. SPONSORING / MONITORING AGENCY NAME(S) AND ADDRESS(ES) 10. SPONSOR/MONITOR’S ACRONYM(S) SERDP Strategic Environmental Research and Development Program 4800 Mark Center Dr, Suite 17D03 11. SPONSOR/MONITOR’S REPORT Alexandria, VA 22350-3605 NUMBER(S) 12. DISTRIBUTION / AVAILABILITY STATEMENT Approved for public release; distribution is unlimited. 13. SUPPLEMENTARY NOTES 14. ABSTRACT The most common secondary explosives and propellants contain nitro groups that are produced using chemical nitration reactions. Conventional manufacturing processes for these energetic materials often use hazardous and corrosive substances, such as nitric acid, and produce hazardous waste streams. Highly reactive nitration reactions can also create multiple isomers and by-products that degrade performance of the energetic products. To reduce the environmental impacts of these processes, new strategies are needed to produce energetic chemicals and precursors. This project identified new bionitration mechanisms used by microorganisms to produce nitro- containing natural products. We investigated biosynthetic pathways for 2-nitroimidazole (azomycin), N-nitroglycine, and nitrophenols. Five new enzymes were discovered to catalyze 2-aminoimidazole and 2-nitroimidazole biosynthesis in a revised pathway from Streptomyces eurocidicus. Stable isotope labeling experiments identified L-arginine and glycine as precursors for the nitramine N-nitroglycine in Streptomyces noursei. Comparative genomic and proteomic analyses identified a set of proteins that could be responsible for N-nitroglycine biosynthesis. Studies of Salegentibacter sp. demonstrated that nitrate reduction to nitrite was associated with bionitration of phenolic substrates, producing a diverse set of nitrophenols. This growing bionitration toolkit represents a diverse range of nitration mechanisms and products that can be adapted for the green chemistry production of nitro compounds and precursors. 15. SUBJECT TERMS Nitration, Biosynthesis, Microorganisms, Energetic compounds, Nitroimidazole, Nitramine, Biosynthesis 16. SECURITY CLASSIFICATION OF: 17. LIMITATION 18. NUMBER 19a. NAME OF RESPONSIBLE PERSON OF ABSTRACT OF PAGES David Graham a. REPORT b. ABSTRACT c. THIS PAGE 19b. TELEPHONE NUMBER (include area UU 56 code) UNCLASSIFIED UNCLASSIFIED UNCLASSIFIED (865)574-0559 Standard Form 298 (Rev. 8-98) Prescribed by ANSI Std. Z39.18 DOCUMENT AVAILABILITY Reports produced after January 1, 1996, are generally available free via US Department of Energy (DOE) SciTech Connect. Website http://www.osti.gov/scitech/ Reports produced before January 1, 1996, may be purchased by members of the public from the following source: National Technical Information Service 5285 Port Royal Road Springfield, VA 22161 Telephone 703-605-6000 (1-800-553-6847) TDD 703-487-4639 Fax 703-605-6900 E-mail [email protected] Website http://classic.ntis.gov/ Reports are available to DOE employees, DOE contractors, Energy Technology Data Exchange representatives, and International Nuclear Information System representatives from the following source: Office of Scientific and Technical Information PO Box 62 Oak Ridge, TN 37831 Telephone 865-576-8401 Fax 865-576-5728 E-mail [email protected] Website http://www.osti.gov/contact.html This report was prepared as an account of work sponsored by an agency of the United States Government. Neither the United States Government nor any agency thereof, nor any of their employees, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise, does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or any agency thereof. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof. ORNL/SPR-2017/498 SERDP Project WP-2332 Final Report Nitration enzyme toolkit for the biosynthesis of energetic materials Author(s) David E. Graham Jim C. Spain Ronald J. Parry Robert L. Hettich Kristina M. Mahan Dawn M. Klingeman Richard J. Giannone Christopher A. Gulvick Tekle T. Fida Date Published: February 5, 2018 Prepared by OAK RIDGE NATIONAL LABORATORY Oak Ridge, TN 37831-6283 managed by UT-BATTELLE, LLC for the US DEPARTMENT OF ENERGY under contract DE-AC05-00OR22725 TABLE OF CONTENTS ABSTRACT ................................................................................................................................................. 1 OBJECTIVE ............................................................................................................................................... 2 BACKGROUND ......................................................................................................................................... 3 NITROIMIDAZOLE BIOSYNTHESIS BY STREPTOMYCES EUROCIDICUS ......................................................... 4 N-NITROGLYCINE (NITRAMINOACETIC ACID) BIOSYNTHESIS BY STREPTOMYCES NOURSEI ...................... 5 NITROAROMATIC BIOSYNTHESIS BY SALEGENTIBACTER ........................................................................... 6 NITRATION REACTIONS IN PYRROLOMYCIN BIOSYNTHESIS...................................................................... 7 PROJECT ORGANIZATION AND WORKFLOW ............................................................................................. 9 MATERIALS AND METHODS ............................................................................................................. 11 CHEMICALS ............................................................................................................................................. 11 BACTERIAL STRAINS AND CULTIVATION ................................................................................................ 11 ANALYTICAL METHODS .......................................................................................................................... 12 Analysis of 2-aminoimidazole and 2-nitroimidazole production ....................................................... 12 Analysis of N-nitroglycine production ............................................................................................... 12 ANALYSIS OF NITROPHENOL PRODUCTION ............................................................................................. 13 Whole cell biotransformations of 2-AI oxidation ............................................................................... 13 Isotope incorporation into N-nitroglycine ......................................................................................... 13 GENOMIC DNA PURIFICATION ............................................................................................................... 14 GENE CLONING AND EXPRESSION ........................................................................................................... 14 Conjugations ...................................................................................................................................... 15 GENOME SEQUENCING ............................................................................................................................ 15 GENOME ANNOTATION AND COMPARATIVE GENOMICS ......................................................................... 15 PROTEOMIC AND
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