William E. Allen
Associate Professor, Organic Chemistry
American Cancer Society Postdoctoral Fellow, University of Texas at Austin (1996-1997)
PhD, University of North Carolina at Chapel Hill (1995)
BS, Washington and Lee University (1990)
Synthesis, Bioorganic Chemistry, and Molecular Recognition
Our research is focused on controlling how molecules bind to one another. In a current small-molecule project, we have prepared highly fluorinated tripodal host compounds (e.g., 1) to selectively extract pollutants like perfluorooctanesulfonate CF3(CF2)7SO3-, “PFOS”) from water. PFOS was historically used in high-volume consumer products like stain-resistant carpeting and food packaging, but is now understood to be bioaccumulative and toxic to mammals. Comparison with hydrocarbon analogs (e.g., 2) should allow us to determine whether 1 benefits from “fluorous-fluorous” interactions between host and guest.
A larger-scale project is inspired by barrel-shaped “porin” proteins found in bacterial cell membranes. Peptides of 7 to 20 residues have been designed to self-assemble into channels. Such superstructures may promote diffusion of targeted analytes through otherwise impermeable lipid bilayers.
Selected Publications
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.
Recent Group Photo (Fall 2007)
(L to R): Lisa Jordan, Toby Allen, Jesse Gavette, Jackie McGrath, Meghan Wagstaff, and Bryant Pollock
