Edward E Fenlon Professor of Chemistry

Biography

View Edward Fenlon's CV

Education

B. S., St. Lawrence University

Ph.D.,  University of Illinois

Research

We use organic synthesis to build molecules for practical purposes. Research projects involve: 

1. 1. The synthesis of nucleotides and proteins with pairs of vibrational reporters (azides, nitriles, and selenocyanates) to measure the distance between them via vibrational coupling observed by 2D IR spectroscopy.
   2. The design and synthesis of air-stable, water-soluble organic radicals such as polarizing agents for dynamic nuclear polarization (DNP). A related project seeks to synthesize bowl-shaped hydrocarbons. 
   3. The history of organic chemistry.
   4. Molecular knots.  
   5. Collaborative work to prepare GM3 synthase to help Amish children.

 

Research Collaborations:

Nucleic Acid Probes

Scott Brewer

Robert Griffin

Ronald Micura

Tim Swager

Matthew Tucker

History of Organic Chemistry

Dr. Brian Myers

 

Grants & Awards

Brewer, S. H.; Fenlon E. E. Investigating Protein and RNA Structure and Dynamics with Vibrational Reporters. National Institutes of Health. National Institute of General Medical Sciences: Academic Research Enhancement Award,  June 2019 through June 2023. $425,256.

National Institute of Health R01 Award (R01GM051501-18A1) to Alexander MacKerell (PI, University of Maryland, Baltimore). Subaward to F&M (Edward Fenlon, Scott Brewer), 7/1/17-6/30/19.

NIH AREA grant - "Investigating Protein Hydration and Structure with Azide Probes." 2014 to 2017. $272,300.

NIH grant - "Development and Application of Multi-Spectroscopic, Site-Specific (MS3) Probes of Nucleic Acid Structure."  June 2010 through May 2013.  $195,895.

Publications

(Undergraduate student coauthor are in bold.)

Hassani, M.; Mallon, C. J.; Monzy, J. N.; Schmitz, A. J.; Brewer, S. H.; Fenlon, E.E.; Tucker, M. J. Inhibition of Vibrational Energy Flow Within an Aromatic Scaffold via Heavy Atom Effect. Journal of Chemical Physics, 2023, 158, 224201.

Lee, B. L.; Papoutsis, B. M.; Wong, N. Y.; Piacentini, J.; Kearney, C.; Huggins, N. A.; Cruz, N.; Ng, T. T.; Hao, K. H.; Kramer, J. S.; Fenlon, E. E.; Nerenberg, P. S.; Phillips-Piro, C. M.; Brewer, S. H. Unraveling Complex Local Protein Environments with 4-Cyano-L-phenylalanine. Journal of Physical Chemistry B, 2022, 126, 8957-8969.

Edward E. Fenlon Double, double trefoil and trouble, Nature Synth. 2022, 1, 586-587. doi.org/10.1038/s44160-022-00103-7

Margolis, E. A.; Keyes, R. J.; Lockey, S. D., IV; Fenlon, E. E.; Design and Synthesis of a Bis-macrocyclic Host and Guests as Building Blocks for Small Molecular Knots. Beilstein J. Org. Chem., 2020, 16, 2314-2321.

Chalyavi, F.; Schmitz, A.; Fetto, N. R.; Tucker, M. J.; Brewer, S.; Fenlon, E. E. Extending the Vibrational Lifetime of Azides with Heavy Atoms. Phys. Chem. Chem. Phs., 2020, 22, 18007-18013.

Chalyavi, F.; Adeyiga, O.; Weiner, J.; Monzy, J.; Schmitz, A.; Nguyen, J.; Fenlon, E. E.; Brewer, S.; Odoh, S.; Tucker, M. J. 2D-IR Studies of Cyanamide (NCN) as a Spectroscopic Reporter of Dynamics in Biomolecules: Uncovering the Origin of Mysterious Peaks. Journal of Chemical Physics, 2020, 152, 074201.

Schmitz, A. J.; Pandey, H. D.; Chalyavi, F.; Shi, T.; Fenlon, E. E.; Brewer, S. H.; Leitner, D. M.; Tucker, M. J. Tuning Molecular Vibrational Energy Flow within an Aromatic Scaffold via Anharmonic Coupling. Journal of Physical Chemistry A, 2019, 123, 10571-10581.

Luo, M.; Eaton, C. N.; Hess, K. R.; Phillips-Piro, C. M.; Brewer, S. H.; Fenlon, E. E. Paired Spectroscopic and Crystallographic Studies of Proteases. Chemistry Select, 2019, 4, 9836-9843.

Schmitz, A. J.; Hogle, D. G.; Gai, X. S.; Fenlon, E. E.; Brewer, S. H.; Tucker, M. J. Two-Dimensional Infrared Study of Vibrational Coupling between Azide and Nitrile Reporters in a RNA Nucleoside. Journal of Physical Chemistry B, 2016, 120, 9387-9394.

Levin, D. E.; Schmitz, A. J.; Hines, S. H.; Hines, K. J.; Tucker, M. J.; Brewer, S. H.; Fenlon, E. E. Synthesis and Evaluation of the Sensitivity and Vibrational Lifetimes of Thiocyanate and Selenocyanate Infrared Reporters. RSC Advances 2016, 6, 36231-36237. 

Tookmanian, E. M.; Philips-Piro, C. M.; Fenlon, E. E.; Brewer, S. H. Azidoethoxyphenylalanine as a Vibrational Reporter and Click Chemistry Partner in Proteins. Chem. Eur. J. 2015, 21, 19096-19103.

Tookmanian, E. M.; Fenlon, E. E.; Brewer, S. H. Synthesis and protein incorporation of azido-modified unnatural amino acids. RSC Advances 2015, 5, 1274-1281.

Fenlon, E. E.; Myers, B. J. Profiles in Chemistry: A Historical Perspective on the National Organic Symposium,  Journal of Organic Chemistry 2013, 78, 5817-5831.

Lipkin, J.S.; Song, R.; Fenlon, E.E.; Brewer, S.H. Modulating Accidental Fermi Resonance: What a Difference a Neutron Makes. Journal of Physical Chemistry Letters 2011, 2, 1672-1676.

Gai, X.S.; Coutifaris, B.A.; Brewer, S.H.; Fenlon, E.E. A Direct Comparison of Azide and Nitrile Vibrational Probes. Physical Chemistry Chemical Physics 2011, 13, 5926-5930.

Tucker, M.J.; Gai, X.S.; Fenlon, E.E.; Brewer, S.H.; Hochstrasser, R.M. 2D IR Photon Echo of Azido-Probes for Biomolecular Dynamics.Physical Chemistry Chemical Physics 2011, 13, 2237-2241.

Gillies, A.T.; Gai, X.S.; Buckwalter, B.L.; Fenlon, E.E.; Brewer, S.H. 15N NMR Studies of a Nitrile-Modified Nucleoside. Journal of Physical Chemistry B 2010, 114, 17136-17141.

Fenlon, E.E. Tying Up Some Loose Ends. Nat. Chem. 2010, 2, 156-157.

Gai, X.S.; Brewer, S.H.; Fenlon, E.E. A Sensitive Multispectroscopic Probe for Nucleic Acids. J. Phys. Chem. B 2010, 113, 7958-7966.

Watson, M. D.; Gai, X. S.; Gillies, A. T.; Brewer, S. H.; Fenlon, E. E. A Vibrational Probe for Local Nucleic Acid Environments: 5-Cyano-2-deoxyuridine. J. Phys. Chem. B 2008, 112, 13188-13192.

Fenlon, E. E. Open Problems in Chemical Topology. Eur. J. Org. Chem. 2008, 5023-5035.

Fenlon, E. E.; Ito, B. R. The Thread & Cut Method: Syntheses of Molecular Knot Precursors. Eur. J. Org. Chem. 2008, 3065-3068.

Silverman, L. N.; Pitzer, M. E.; Ankomah, P. O.; Boxer, S. C.; Fenlon, E. E.. Vibrational Stark Effect Probes for Nucleic Acids. J. Phys. Chem. B 2007 111, 11611-11613.

Courses Taught

Chem 211: Organic Chemistry I: Structure and Function of Carbon-Containing Compounds, Lecture & Lab

Chem 212: Organic Chemistry II: Reactivity and Synthesis of Organic Molecules, Lecture & Lab

Chem 323 - Medicinal Chemistry

​CNX 230 - Mars & Venus on the Pill