William E. Allen

Professor
Organic Chemistry

Office: SZ 536
Phone: 252-328-9779
E-mail: allenwi@ecu.edu

  • American Cancer Society Postdoctoral Fellow, University of Texas at Austin (1996-1997)
  • Ph.D., University of North Carolina at Chapel Hill (1995)
  • B.S., Washington and Lee University (1990)

Synthesis, Bioorganic Chemistry, and Molecular Recognition

Making proteins glow: Arginine has the most basic side-chain of the 20 standard amino acids. With a pKa of 13.8, its guanidine unit is protonated under all biologically relevant aqueous conditions. Counterintuitively, it remains cationic even within the water-scarce interiors of folded proteins, and when it is in contact with the nonpolar core of lipid bilayers. With a goal of driving membrane localization of peptides through application of external stimuli, we have prepared a arginine derivative that can shed H+ through excited-state proton transfer (ESPT). To our knowledge, it is the first Arg derivative in which the guanidinium pi-system is in direct electronic communication with a fluorophore.

Nature’s antifreeze: Fish, frogs, and simpler organisms like tardigrades use carbohydrate-based compounds to survive freezing conditions. We are developing new fluorescent tools to understand how such antifreeze molecules inhibit ice crystal growth and protect cells from damage.

Selected Publications

Keever, J. M.; Banzon, P. D.; Hales, M. K.; Sargent, A. L.; Allen. W. E. “Association Between N-Terminal Pyrenes Stabilizes the Collagen Triple Helix,” J. Org. Chem. 2023, 88, 11885-11994. (https://doi.org/10.1021/acs.joc.3c01175)

Walker, J. P.; Allen, W. E.; Clevenger, L.; Hosbein, K. N.; Kennedy, A. M.; Vance-Chalcraft, H.; Whiting, B. “Course-Based Undergraduate Research Experiences as a Community of Practice (CoP),” J. Chem. Educ. 2023, 100, 2520-2528. (https://doi.org/10.1021/acs.jchemed.2c00844)

Allen, W. E.; Hosbein, K. N.; Kennedy, A. M.; Whiting, B.; Walker, J. P. “Design and Implementation of an Organic to Analytical CURE Sequence,” J. Chem. Educ. 2021, 98, 2199-2208. (https://doi.org/10.1021/acs.jchemed.1c00129)

Allen, W. E.; Hosbein, K. N.; Kennedy, A. M.; Whiting, B.; Walker, J. P. “Embedding Research Directly into the Chemistry Curriculum with an Organic to Analytical Sequence,” J. Chem. Educ. 2021, 98, 2188-2198. (https://doi.org/10.1021/acs.jchemed.0c01263)

Ohler, A.; Long, H.; Ohgo, K.; Tyson, K.; Murray, D.; Davis, A.; Whittington, C.; Hvastkovs, E. G.; Duffy, L.; Haddy, A.; Sargent, A. L.; Allen, W. E.; Offenbacher, A. R. “Synthesis of redox-active fluorinated 5-hydroxytryptophans as molecular reporters for biological electron transfer,” Chem. Commun. 2021, 57, 3107-3110. (https://doi.org/10.1039/D1CC00187F)

Marshall, S. R.; Stoudt, M. L.; DiVittorio, M. A.; Sargent, A. L. Allen, W. E. “Side-Chain Protonation States of a Fluorescent Arginine,” J. Org. Chem. 2019, 84, 14407-14413. (https://doi.org/10.1021/acs.joc.9b00677)

Wercholuk, A. N.; Thuman, J. M.; Stanley, J. L.; Sargent, A. L.; Anderson, E. S.; Allen, W. E. “Incorporation of Fluorophore-Cholesterol Conjugates into Liposomal and Mycobacterial Membranes,” Bioorg. Med. Chem. 2016, 24, 1045-1049. (http://dx.doi.org/10.1016/j.bmc.2016.01.030)

Farrell, D. P.; Sargent, A. L. Allen, W. E. “Anion Binding by Fluorescent Fmoc-Protected Amino Acids,” Supramol. Chem. 2016, 28, 45-52. (http://dx.doi.org/10.1080/10610278.2015.1073289)

Chai, H.; Allen, W. E.; Hicks, R. P. “Spectroscopic Investigations of the Binding Mechanisms between Antimicrobial Peptides and Membrane Models of Pseudomonas aeruginosa and Klebsiella pneumoniae,” Bioorg. Med. Chem. 2014, 22, 4210-4222. (https://doi.org/10.1016/j.bmc.2014.05.040)

Chai, H.; Allen, W. E.; Hicks, R. P. “Synthetic Antimicrobial Peptides Exhibit Two Different Binding Mechanisms to the Lipopolysaccharides Isolated from Pseudomonas aeruginosa and Klebsiella pneumoniae,” Int. J. Med. Chem. 2014, Article ID 809283, 13 pp. (http://dx.doi.org/10.1155/2014/809283)

Jessen, D. M.; Wercholuk, A. N.; Xiong, B.; Sargent, A. L.; Allen, W. E. “Dimerization and Anion Binding of a Fluorescent Phospholipid Analogue,” J. Org. Chem. 2012, 77, 6615-6619.

Jordan, L. M.; Boyle, P. D.; Sargent, A. L.; Allen, W. E. “Binding of Carboxylic Acids by Fluorescent Pyridyl Ureas,” J. Org. Chem. 2010, 75, 8450-8456.

Gavette, J. V.; McGrath, J. M.; Spuches, A. M.; Sargent, A. L.; Allen, W. E. “Fluorous Effects in Amide-Based Receptors for Anions,” J. Org. Chem. 2009, 74, 3706-3710.

Gavette, J. V.; Sargent, A. L.; Allen, W. E. “Hydrogen Bonding vs Steric Gearing in a Hexasubstituted Benzene,” J. Org. Chem. 2008, 73, 3582-3584.