William E. Allen

Title: Associate Professor, Organic Chemistry
Office: SZ 536
Phone: (252)328-9779

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
Adding new functionality to old biomolecules: 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. Among the functional roles for Arg residues, the presence of multiple persistent positive charges appears essential to the cell-penetrating power of certain peptides. With a goal of driving membrane localization of peptides through application of external stimuli, we have prepared an 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 p-system is in direct electronic communication with a fluorophore.

Dr. Allen Research Picture

Selected Publications

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.

Farrell, D. P.; Sargent, A. L.; Allen, W. E. "Anion binding by fluorescent Fmoc-protected amino acids," Supramol. Chem. 2016, 28, 45-52. 

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. vol. 2014, Article ID 809283, 2014. doi:10.1155/2014/809283

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.

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.

Gavette, J. G.; 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.

Gavette, J. G.; Sargent, A. L.; Allen, W. E. "Hydrogen Bonding vs Steric Gearing in a Hexasubstituted Benzene," J. Org. Chem. 2008, 73, 3582.

Barnhill, D. K.; Sargent, A. L.; Allen, W. E. "Participation of Host 'Spacer' Atoms in Carboxylic Acid Binding: Implications for Amino Acid Recognition," Tetrahedron 2005, 65, 8366.

Ma, L.; Morgan, J. C.; Stancill, W. E.; Allen, W. E. "Phosphorylated 1,6-Diphenyl-1,3,5-Hexatriene," Bioorg. Med. Chem. Lett. 2004, 14, 1075.

Sargent, A. L.; Hawkins, I. C.; Allen, W. E.; Liu, H.; Sessler, J. L.; Fowler, C. J. "Global vs. Local Aromaticity in Porphyrinoid Macrocycles: Experimental and Theoretical Study of 'Imidacene,' an Imidazole-Containing Analogue of Porphycene," Chem. Eur. J., 2003, 9, 3065.

Causey, C. P.; Allen, W. E. "Anion Binding by Fluorescent Biimidazole Diamides," J. Org. Chem. 2002, 67, 5963.

Allen, W. E.; Fowler, C. J.; Lynch, V. M.; Sessler, J. L. "Self-Assembled Helices from 2,2´-Biimidazoles," Chem. Eur. J. 2001, 7, 721-729