Faculty Assistant

Pattie Faranetta
Frick Laboratory, 228

Research Focus

John T. Groves video interviewThe major thrust of our research program is at the interface of organic, inorganic, and biological chemistry. Many biochemical transformations as well as important synthetic and industrial processes are catalyzed by metals. Current effort focus on the design of new, biomimetic catalysts and the molecular mechanisms of these processes, the design and assembly of large scale membrane-protein-small molecule constructs, studies of host-pathogen interactions related to iron acquisition by small molecule siderophores and molecular probes of the role of peroxynitrite in biological systems.

Research Areas
Catalysis / Synthesis
Chemical Biology
Inorganic Chemistry

American Chemical Society National Award in Inorganic Chemistry (2015)

Sigma-Aldrich Award in Inorganic Chemistry, Northwestern University (2015)

Rayson Huang Prize and Lectureship in Chemistry, University of Hong Kong (2015)

National Academy of Sciences (2012)

Ira Remsen Award, American Chemical Society (2010)

Hans Fischer Award in Porphyrin Chemistry, Hans Fischer Gesellschaft (Munich), (2010)

Keller Center Award for Innovation and Entrepreneurship, Princeton University (2010)

Fellow of the Royal Society of Chemistry (2009-)

Frontiers in Biological Chemistry Award, Max Planck Institute (2009)

Grand Prix, Maison de la Chimie (Paris) Laureate, for contributions to mankind and nature (2008)

National Science Foundation Extension Award for Special Creativity (2008-2011)

National Institute of General Medical Sciences, NIH, MERIT Award (2007-2017)

Cady Distinguished Lecturer, University of Washington (2007)

Distinguished Visiting Professor University of Hong Kong (2003)

Distinguished Lecturer in Inorganic Chemistry, Northwestern University (2000)

Abbott Distinguished Lecturer in Organic Chemistry, Colorado State University (2000)

Alfred Bader Award in Bioorganic and Bioinorganic Chemistry, American Chemical Society (1996)

Eli Lilly Distinguished Lecturer, Indiana University (1997)

Bergmann Lectureship, Yale University (1997

Fellow, Japan Society for the Promotion of Science (1987 and 1997)

Fellow, American Academy of Arts and Sciences (1993-)

Morris S. Kharasch Visiting Professor, University of Chicago (1993)

Hugh Stott Taylor Chair of Chemistry, Princeton University (1991-)

A. C. Cope Scholar Award, American Chemical Society, 1991)

National Science Foundation Extension Award for Special Creativity (1990-1992)

Nichols Distinguished Lecturer (1989)

Fellow, American Association for the Advancement of Science (1984)

Phi Lambda Upsilon Award for Teaching and Leadership (1978)

L. P. Hammett Award for Outstanding Graduate Research, Columbia University (1969)

Selected Recent Publications

Courtney F. McQueen and John T. Groves, A reevaluation of iron binding by Mycobactin J, J. Biol. Inorg. Chem. 2018, 23, 995-1007. DOI: 10.1007/s00775-018-1592-2. [Full Text PDF]

Micah T. Nelp, Patrick A. Kates, John T. Hunt, John A. Newitt, Aaron Balog, Derrick Maley, Xiao Zhu, Lynn Abell, Alban Allentoff, Robert Borzilleri, Hal A. Lewis, Zeyu Lin, Steven P. Seitz, Chunhong Yan, John T. Groves, The immune modulating enzyme indoleamine 2,3-dioxygenase is effectively inhibited by targeting its apo-form, Proc. Nat. Acad. Sci. USA, 2018, 115, 3249-3254; doi/10.1073/pnas.1719190115. [Full Text PDF]

Nichole A. Schwartz, Nicholas C. Boaz, Steven E. Kalman, Thompson Zhuang, Jonathan M. Goldberg, Ross Fu, Robert J. Nielsen, William A. Goddard III, John T. Groves, T. Brent Gunnoe, Mechanism of Hydrocarbon Functionalization by an Iodate/Chloride System: The Role of Ester Protection, ACS Catalysis, 2018, 8, DOI: 10.1021/acscatal.7b04397. [Full Text PDF]

Gang Li, Andrew K. Dilger, Peter T. Cheng, William R. Ewing, John T. Groves, Selective C-H Halogenations with a Fluorinated Manganese Porphyrin, Angew. Chem.2018, 57, 1251-1255. DOI: 10.1002/anie.201710676. [Full Text PDF]

Wei Liu, Xiongyi Huang, Micheal Placzek, Shane W. Krska, Paul McQuade, Jacob M. Hooker, John T. Groves, Site-selective 18F fluorination of unactivated C-H bonds mediated by a manganese porphyrin, Chem. Sci., 2017, DOI: 10.1039/C7SC04545J. [Full Text PDF]

Xiongyi Huang, Thompson Zhuang, Patrick A. Kates, Hongxin Gao, Xinyi Chen, and John T. Groves, Alkyl Isocyanates via Manganese-Catalyzed C-H Activation for the Preparation of Substituted Ureas , J. Am. Chem. Soc. 2017, 139, 15407-15413. DOI: 10.1021/jacs.7b07658. [Full Text PDF]

Nichole A. Schwartz, Shunyan Gu, Bradley A. McKeown, Xiongyi Huang, Nicholas C. Boaz, T. Brent Gunnoe, John T. Groves, Studies of C­­­­-H Activation and Functionalization: Combined Computational and Experimental Efforts to Elucidate Mechanisms, Principles and Catalysts Springer, 2018, in press.

Xiongyi Huang and John T. Groves, Oxygen activation and radical transformations in heme proteins and metalloporphyrins, Chem. Rev. 2018, 118, 2491−2553; published online December 29, 2017 DOI: 10.1021/acs.chemrev.7b00373. [Full Text PDF]

Ross Fu, Robert J. Nielsen, Nichole A. Schwartz, William A. Goddard III, T. Brent Gunnoe, John T. Groves, DFT mechanistic study of methane monooxygenation by hypervalent iodine alkane oxidation (HIAO) process, J. Phys. Chem., 2018, 8, in review.

Chun H. Hsieh, Xiongyi Huang, José A. Amaya, Cooper D. Rutland, Carson L. Keys, John T. Groves, Rachel N. Austin, Thomas M. Makris, The Enigmatic P450 Decarboxylase OleT is Capable of, but Evolved to Frustrate, Oxygen Rebound Chemistry, Biochemistry 2017, 56, 3347-3357.  DOI: 10.1021/acs.biochem.7b00338. [Full Text PDF]

Wei Liu, Mu-Jeng Cheng, Robert J. Nielsen, William A. Goddard III, and John T. Groves, Probing the C-O bond-formation step in metalloporphyrin catalyzed C-H oxygenation reactions, ACS Catalysis, 2017, 7, 4182-4188, DOI: 10.1021/acscatal.7b00655. [Full Text PDF]

Hongxin Gao and John T. Groves,  Fast Hydrogen Atom Abstraction by a Hydroxo Iron(III) Porphyrazine, J. Am. Chem. Soc. 2017, 139, 3938-3941, DOI:10.1021/jacs.6b13091. [Full Text PDF]

Xiongyi Huang and John T. Groves, Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C-H activation, J. Biol. Inorg. Chem. 2017, 22, 185–207 DOI 10.1007/s00775-016-1414-3. [Full Text PDF]

Xiongyi Huang and John T. Groves, Taming Azide Radicals for Catalytic C-H Azidation, ACS Catalysis, 2016, 6, 751−759. DOI: 10.1021/acscatal.5b02474.

Hsieh, C. H., Huang, X., Keys, C. L. Groves, J. T., Austin, R. N., Makris, T. M., Mechanism and Catalytic Potential of a Cytochrome P450 (OleT) that Catalyzes C-C Bond Scission, FASEB J., 2016, 30, S608.3

Groves, J.T. Cytochrome P450 Enzymes: Understanding the Biochemical Heiroglyphs, F1000Research 2015, 4(F1000 Faculty Rev):178 [Full Text PDF]

Liu, W., Groves, J.T. Manganese-catalyzed C-H Halogenation, Accounts Chem. Res., 2015, 48, 1727-1735 [Full Text PDF]

Huang, X.; Bergsten, T.; Groves, J.T. Manganese-catalyzed Late-stage Aliphatic C-H Azidation, J. Am. Chem. Soc., 2015, 137, 5300-5303 [Full Text PDF]

Boaz, N.; Bell, S.R.; Groves, J.T. Ferryl Protonation in Oxoiron(IV) Porphyrins and its Role in Oxygen Transfer, J. Am. Chem. Soc., 2015, 137 (8), 2875-2885 [Full Text PDF]

Huang, X.; Liu, W.; Hooker, J.M.; Groves, J.T. Targeted Fluorination with ­­­Fluoride Ion via Manganese-Catalyzed Decarboxylation, Angew. Chem. Int. Ed., 2015, 54, 5241-5245 [Full Text PDF]

Wang, X.; Ullrich, R.; Hofrichter, M.; Groves, J.T. The Heme-thiolate Ferryl of Aromatic Peroxygenase is Basic and Reactive, Proc. Nat. Acad. Sci. U.S.A., 2015, 112 (12), 3686-3691 [Full Text PDF]

Kalman, S.E.; Munz, D.; Fortman, G.C.; Boaz, N.C.; Groves, J.T.; Gunnoe, B.T. Partial Oxidation of Light Hydrocarbons Using Periodate and Chloride Salts, Dalton Trans., 2015, 44, 5294-5298 [Full Text PDF]

Stavniichuk, R.; Shevalye, H.; Lupachyk, S.; Obrosov, A.; Groves, J.T.; Obrosova, I.G.; Yorek, M.A. Peroxynitrite and Protein Nitration in the Pathogenesis of Diabetic Peripheral Neuropathy, Diabetes/Metabolism Research and Reviews, 2014, 30, 669-678 [Full Text PDF]

Konnick, M.M.; Hashiguchi, B.G.; Devarajan, D.; Boaz, N.C.; Gunnoe, B.T.; Groves, J.T.; Ess, D.H.; Periana, R.A. Selective CH Oxy-Functionalization of Methane, Ethane and Propane by a Perfluoroarene Iodine (III) Complex, Angew. Chem. Int. Ed., 201453, 10490-10494 [Full Text PDF]

Groves, J.T.; Boaz, N.C. Fishing for the Peroxidase Protons, Science, 2014, 345, 142-143 [Full Text PDF]

Groves, J. T., "Enzymatic C-H bond activation - Using push to get pull." Nature Chemistry 2014, 6 (2), 89-91.

Pahls, D. R.; Groves, J. T.; Gunnoe, T. B.; Cundari, T. R., "Theoretical Study of Reductive Functionalization of Methyl Ligands of Group 9 Complexes Supported by Two Bipyridyl Ligands: A Key Step in Catalytic Hydrocarbon Functionalization." Organometallics 2014, 33 (8), 1936-1944.

O'Reilly, M. E.; Pahls, D. R.; Webb, J. R.; Boaz, N. C.; Majumdar, S.; Hoff, C. D.; Groves, J. T.; Cundari, T. R.; Gunnoe, T. B., "Reductive functionalization of a rhodium(III)-methyl bond by electronic modification of the supporting ligand." Dalton Transactions 2014, 43 (22), 8273-8281.

Huang, X.; Liu, W.; Ren, H.; Neelamegam, R.; Hooker, J. M.; Groves, J. T., "Late Stage Benzylic C-H Fluorination with F-18 Fluoride for PET Imaging." Journal of the American Chemical Society 2014, 136 (19), 6842-6845.

Fortman, G. C.; Boaz, N. C.; Munz, D.; Konnick, M. M.; Periana, R. A.; Groves, J. T.; Gunnoe, T. B., "Selective Monooxidation of Light Alkanes Using Chloride and Iodate." Journal of the American Chemical Society 2014, 136 (23), 8393-8401.

Groves, J. T.; Boaz, N. C., "Fishing for peroxidase protons." Science 2014, 345 (6193), 142-143.

Bertrand, E. M.; Keddis, R.; Groves, J. T.; Vetriani, C.; Austin, R. N., "Identity and mechanisms of alkane-oxidizing metalloenzymes from deep-sea hydrothermal vents." Frontiers in Microbiology 2013, 4.

Liu, W.; Huang, X.; Groves, J. T., "Oxidative aliphatic C-H fluorination with manganese catalysts and fluoride ion." Nature Protocols 2013, 8 (12), 2348-2354.

Liu, W.; Groves, J. T., "Manganese-Catalyzed Oxidative Benzylic C-H Fluorination by Fluoride Ions." Angewandte Chemie-International Edition 2013, 52 (23), 6024-6027.

 Wang, X.; Peter, S.; Ullrich, R.; Hofrichter, M.; Groves, J. T., "Driving Force for Oxygen-Atom Transfer by Heme-Thiolate Enzymes." Angewandte Chemie-International Edition 2013, 52 (35), 9238-9241.

Bergstrom, C. L.; Beales, P. A.; Lv, Y.; Vanderlick, T. K.; Groves, J. T., "Cytochrome c causes pore formation in cardiolipin-containing membranes." Proceedings of the National Academy of Sciences of the United States of America 2013, 110 (16), 6269-6274.

Wang, D.; Groves, J. T., "Efficient water oxidation catalyzed by homogeneous cationic cobalt porphyrins with critical roles for the buffer base." Proceedings of the National Academy of Sciences of the United States of America 2013, 110 (39), 15579-15584.

Naing, S.-H.; Parvez, S.; Pender-Cudlip, M.; Groves, J. T.; Austin, R. N., "Substrate specificity and reaction mechanism of purified alkane hydroxylase from the hydrocarbonoclastic bacterium Alcanivorax borkumensis (AbAlkB)." Journal of Inorganic Biochemistry 2013, 121, 46-52.

Callaghan, A. V.; Morris, B. E. L.; Pereira, I. A. C.; McInerney, M. J.; Austin, R. N.; Groves, J. T.; Kukor, J. J.; Suflita, J. M.; Young, L. Y.; Zylstra, G. J.; Wawrik, B., "The genome sequence of Desulfatibacillum alkenivorans AK-01: a blueprint for anaerobic alkane oxidation." Environmental Microbiology 2012, 14 (1), 101-113.

Radovits, T.; Beller, C. J.; Groves, J. T.; Merkely, B.; Karck, M.; Szabo, C.; Szabo, G., "Effects of FP15, a peroxynitrite decomposition catalyst on cardiac and pulmonary function after cardiopulmonary bypass." European Journal of Cardio-Thoracic Surgery 2012, 41 (2), 391-396.

Pouy, M. J.; Milczek, E. M.; Figg, T. M.; Otten, B. M.; Prince, B. M.; Gunnoe, T. B.; Cundari, T. R.; Groves, J. T., "Flavin-Catalyzed Insertion of Oxygen into Rhenium-Methyl Bonds." Journal of the American Chemical Society 2012, 134 (31), 12920-12923.

Wang, X.; Peter, S.; Kinne, M.; Hofrichter, M.; Groves, J. T., "Detection and Kinetic Characterization of a Highly Reactive Heme-Thiolate Peroxygenase Compound I." Journal of the American Chemical Society 2012, 134 (31), 12897-12900.

Cooper, H. L. R.; Mishra, G.; Huang, X.; Pender-Cudlip, M.; Austin, R. N.; Shanklin, J.; Groves, J. T., "Parallel and Competitive Pathways for Substrate Desaturation, Hydroxylation, and Radical Rearrangement by the Non-heme Diiron Hydroxylase AlkB." Journal of the American Chemical Society 2012, 134 (50), 20365-20375.

Szabo, G.; Loganathan, S.; Merkely, B.; Groves, J. T.; Karck, M.; Szabo, C.; Radovits, T., "Catalytic peroxynitrite decomposition improves reperfusion injury after heart transplantation." Journal of Thoracic and Cardiovascular Surgery 2012, 143 (6), 1443-1449.

Liu, W.; Huang, X.; Cheng, M.-J.; Nielsen, R. J.; Goddard, W. A., III; Groves, J. T., "Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin." Science 2012, 337 (6100), 1322-1325.

Austin, R. N.; Groves, J. T., "Alkane-oxidizing metalloenzymes in the carbon cycle." Metallomics 2011, 3 (8), 775-787.

Beales, P. A.; Bergstrom, C. L.; Geerts, N.; Groves, J. T.; Vanderlick, T. K., "Single Vesicle Observations of the Cardiolipin-Cytochrome c Interaction: Induction of Membrane Morphology Changes." Langmuir 2011, 27 (10), 6107-6115.

Umile, T. P.; Groves, J. T., "Catalytic Generation of Chlorine Dioxide from Chlorite Using a Water-Soluble Manganese Porphyrin." Angewandte Chemie-International Edition 2011, 50 (3), 695-698.

Umile, T. P.; Wang, D.; Groves, J. T., "Dissection of the Mechanism of Manganese Porphyrin-Catalyzed Chlorine Dioxide Generation." Inorganic Chemistry 2011, 50 (20), 10353-10362.

Golisz, S. R.; Gunnoe, T. B.; Goddard, W. A., III; Groves, J. T.; Periana, R. A., "Chemistry in the Center for Catalytic Hydrocarbon Functionalization: An Energy Frontier Research Center." Catalysis Letters 2011, 141 (2), 213-221.