UNIVERSITY OF WISCONSIN River Falls

Faculty and Staff

O'Reilly, Matthew

Matthew O'Reilly

Matthew O'Reilly

Assistant Professor

Chemistry and Biotechnology
Office: 253 Centennial Science Hall
Phone:

Email: matthew.oreilly@uwrf.edu

Education:

  • BS: Xavier University, 2009
  • PhD: Vanderbilt University, 2014
  • Postdoctoral Studies: University of Wisconsin-Madison, 2017

Courses Taught:

  • CHEM 231 Organic Chemistry I
  • CHEM 232 Organic Chemistry II
  • CHEM 236 Organic Chemistry I Laboratory
  • CHEM 237 Organic Chemistry II Laboratory
  • CHEM 333 ;Organic Synthesis
  • CHEM 334 Organic Synthesis Laboratory
  • BIOT / CHEM 380 Junior Seminar

Research Interests:

  • Organic chemistry methods development. Students working with me will attempt to make biologically important small molecule scaffolds in new and innovative ways. My specific interests involve asymmetric organocatalysis, which uses chiral organic molecules to catalyze enantioselective reactions. 
  • Antibiotic discovery and evaluation. Students working with me will synthesize small organic molecules that may be effective at inhibiting bacterial growth. This research area is more interdisciplinary, as students will use standard organic chemistry methods to synthesize compounds and they will learn microbiological techniques to test these molecules in biological systems.

Publications

(undergraduate coauthors underlined)

  • O’Reilly, M. C.; Karlen, K. M.; Kumar, S. K.; Blackwell, H. E. ‘Systematic Evaluation of the Triphenyl Scaffold as a Modulator of Quorum Sensing in Pseudomonas aeruginosa: Structure Activity Relationships, Mode Switching, and Target Switching.’ In Preparation.
  • Manson, D. M.; O’Reilly, M. C.; Blackwell, H. E. ‘Exploration of the structure activity relationships of V-O6-018.’ In Preparation.
  • O’Reilly, M. C.; Dong, S.; Rossi, F. A.; Karlen, K. M.; Kumar, R. S.; Nair, S. K.; Blackwell, H. E. ‘Structural and Biochemical Studies of Non-native Agonists of the LasR Quorum-Sensing Receptor Reveal an L3 Loop “Out” Conformation for LasR.’ Cell Chemical Biology 2018, 25, 1128-1139.
  • O’Reilly, M. C.; Blackwell, H. E. ‘Structure-Based Design and Biological Evaluation of Triphenyl Scaffold-Based Hybrid Compounds as Hydrolytically Stable Modulators of a LuxR-Type Quorum Sensing Receptor.’ ACS Infectious Diseases 2016, 2, 32-38.
  • Senter, T. J.; O’Reilly, M. C.; Chong, K. M.; Sulikowski, G. A.; Lindsley, C. W. ‘A General, Enantioselective Synthesis of N-Alkyl Terminal Aziridines and C2-Functionalized Azetidines via Organocatalysis.’ Tetrahedron Letters 2015, 56, 1276-1279.
  • Scott S. A.; Spencer C. T.; O’Reilly, M. C.; Brown, K. A.; Cho, C.; Jung, J.; Larock, R.; Brown, H. A.; Lindsley, C. W. ‘Discovery of desketoraloxifene analogs as inhibitors of mammalian, Pseudomonas aeruginosa, and NAPE phospholipase D enzymes.’ ACS Chemical Biology 2015, 10, 421-432.
  • O’Reilly, M. C.; Scott, S. A.; Brown, H. A.; Lindsley, C. W. ‘Further evaluation of novel structural modifications to scaffolds that engender PLD isoform selective inhibition.’ Bioorganic and Medicinal Chemistry Letters. 2014, 24, 5553-5557.
  • O’Reilly, M. C.; Oguin III, T. H.; Scott, S. A.; Thomas, P. G.; Locuson, C. W.; Morrison, R. D.; Daniels, J. S.; Brown, H. A.; Lindsley, C. W. ‘Discovery of a highly selective PLD2 inhibitor, VU0468809 (ML395): a new probe with improved physiochemical properties and broad spectrum antiviral activity against influenza strains.’ ChemMedChem. 2014, 9, 2633-2637.
  • Scott, S. A.; Xiang, Y.; Mathews, T. P.; Plumley, H. C.; Myers, D. S.; Armstrong, M. D.; O’Reilly, M. C.; Lindsley, C. W.; Brown, H. A. ‘Regulation of Phospholipase D activity and phosphatidic acid production downstream of the Purinergic (P2Y6) receptor.’ Journal of Biological Chemistry 2013, 288, 20477-20487.
  • O’Reilly, M. C.; Lindsley C. W. ‘A general, enantioselective synthesis of ? and ?-fluoroamines.’ Tetrahedron Letters 2013, 54, 3627-3629.
  • O’Reilly, M. C.; Scott, S. A.; Brown, K. A.; Oguin III, T. H.; Thomas, P. G.; Daniels, J. S.; Morrison, R.;  Brown, H. A.; Lindsley, C. W. ‘Development of dual PLD1/2 and PLD2 selective inhibitors from a common 1,3,8-triazaspiro[4.5]decane core: discovery of ML298 and ML299 that decrease invasive migration in U87-MG glioblastoma cells.’ Journal of Medicinal Chemistry 2013, 56, 2695-2699.
  • O’Reilly, M.C.; Lindsley, C.W. ‘A general, enantioselective synthesis of protected morpholines and piperazines.’ Organic Letters 2012, 14; 2910-2913.
  • O’Reilly, M.C.; Lindsley, C.W. ‘Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N’-protected piperazines via organocatalysis.’ Tetrahedron Letters 2012, 53, 1539-1542.
  • Mullins, R. J.; O’Reilly, M. C. ‘Houben-Hoesch Reaction’ in Name Reactions for Carbocyclic Ring Formations, Li, J. J. John Wiley & Sons, Inc.,  2010, pp 675-687.

Presentations

(undergraduate authors underlined)

  • Jon FarrenJohn LoweryAlan FalkowskiMatthew C. O’Reilly. “Discovery of emmacin-related antibacterial compounds.” Abstracts of Presentation Papers, 12th Annual WSTS, Menomonie, WI July 22-23, 2019.
  • Kirsten J. RuudMatthew C. O’Reilly. “Studies toward a general and enantioselective synthesis of 2-substituted and 2,3-disubstituted azetidines using organocatalysis.” Abstracts of Presentation Papers, 257th ACS National Meeting and Exposition, Orlando, FL March 31-April 4, 2019.
  • Kirsten J. RuudMatthew C. O’Reilly. “The development of organocatalytic methods towards the enantioselective synthesis of azetidines.” UW-River Falls Fall Gala, River Falls, WI, December 2018.
  • John LoweryAlan FalkowskiMatthew C. O’Reilly. “Synthesis of an anti-MRSA DHFR inhibitor.” UW-River Falls Fall Gala, River Falls, WI, December 2018.

Fellowships

  • Arnold and Mabel Beckman Postdoctoral Fellowship
  • Ruth L. Kirschstein National Research Service Award (declined)
  • The American Chemical Society's Division of Medicinal Chemistry Predoctoral Fellowship
  • Vanderbilt Institute of Chemical Biology Predoctoral Fellowship

Highlights of Postdoctoral Work

View video here