Students working in my group are interested in a wide variety of topics, ranging from the application of experimental and theoretical methods to study of the interaction of molecules with their environment at the atomic level, to the design and synthesis of molecules with protozoocidal activity.

For example, we are currently investigating how ionic liquids (ILs), a new class of solvents composed solely of ions, which show promise as ‘green’ materials, solvate polysaccharides such as cellulose and starch. Among the techniques we employ are nuclear magnetic resonance (NMR) spectroscopy and molecular dynamic (MD) simulations. Our studies so far have allowed us to determine that an important class of ILs, the N,N’-dialkylimidazolium chlorides, solvate carbohydrates through the formation of hydrogen bonds between the IL anions and the hydroxyl groups on the sugar solutes. In the case of cellulose and starch, these interactions disrupt the intricate intra-and inter-molecular hydrogen bonding network present, leading to their dissolution. Together with results from current and future work in this area, these findings will allow us to develop new IL-based ‘green’ solvent systems and technologies for the extraction, processing, and analysis of polymeric carbohydrates, which could have important industrial applications.

Another active area of research in my group deals with the use of easily-accessible NMR parameters, such as chemical shifts and coupling constants, to study the dynamics and conformational preferences of carbohydrates and small molecules bound to their protein receptors. This information is critical for medicinal chemists studying molecular recognition phenomena or involved in the rational design of novel drugs. Our efforts have so far led to the development of the 13C Chemical Shift Surface methodology and the Shift DIrected LIgand CONformation approach (SDILICON). Some of these computational tools are currently being used by a number of academic and industrial groups.

Finally, several students in my laboratory are working on the development of novel classes of compounds with potential protozoocidal activity. So far, and through the use of well-established chemistries and employing readily available starting materials, we have been able to prepare a large number of compounds active against a variety of parasitic diseases, such as malaria, Chagas, Leishmaniasis, and trypanosomiases.

‡ Undergraduate Student
* Graduate Student

Liu, Z.; Remsing, R. C.‡; Moore, P. B.; Moyna, G. "Molecular Dynamics Study of the Mechanism of Cellulose Dissolution in the Ionic Liquid 1-n-Butyl-3-Methylimidazolium Chloride", in Ionic Liquids: Not Just Solvents Anymore, Brennecke, J. F., Rogers, R. D., Seddon, K. R., Eds. ACS Symposium Series 975, American Chemical Society: Washington, DC, 2007 (in press).

Remsing, R. C.‡; Rapp, A. L.‡; Wildin, J. L.‡; Moyna, G., "Hydrogen-Bonding in Ionic Liquids Revisited: An NMR Study of Deuterium Isotope Effects in 1-n-Butyl-3-Methylimidazolium Chloride", J. Phys. Chem. B 2007, 111, 11619-11621.

Khrizman, A.‡; Moulthrop, J. S.‡; Little, S.; Wharton, H.; Yardley, V.; Moyna, G., "Synthesis and In Vitro Protozoocidal Activity of Diazabicyclo Benzotropolone Derivatives", Bioorg. Med. Chem. Lett. 2007, 17, 4183-4186.

Fort, D. A.*; Remsing, R. C.‡; Swatloski, R. P.; Moyna, P.; Moyna, G.; Rogers, R. D., "Can Ionic Liquids Dissolve Wood? Processing and Analysis of Lignocellulosic Materials with 1-n-Butyl-3-Methylimidazolium Chloride, Green Chem. 2007, 9, 63-69.
(Listed as a “Top Ten” most accessed articles in Green. Chem. for the months of January and February 2007).

Remsing, R. C.‡; Swatloski, R. P.; Rogers, R. D.; Moyna, G., "Mechanism of Cellulose Dissolution in the Ionic Liquid 1-n-Butyl-3-Methylimidazolium Chloride: A ¹³C and ^35/37Cl NMR Relaxation Study on Model Systems", Chem. Commun. 2006, 1271-1273.

Fort, D. A.*; Swatloski, R. P.; Moyna, P.; Rogers, R. D.; Moyna, G., "Use of Ionic Liquids in the Study of Fruit Ripening by High-Resolution ¹³C NMR Spectroscopy: ‘Green’ Solvents Meet Green Bananas", Chem. Commun. 2006, 716-718.

Sergeyev, I.‡; Moyna, G., "Determination of the Three-Dimensional Structure of Oligosaccharides in the Solid State from Experimental ¹³C NMR Data and Ab Initio Chemical Shift Surfaces, Carbohydrate Res. 2005, 340, 1165-1174.

Moulthrop, J. S.‡; Swatloski, R. P.; Moyna, G; Rogers, R. D., "High-Resolution ¹³C NMR Studies of Cellulose and Cellulose Oligomers in Ionic Liquid Solutions", Chem. Commun. 2005, 1557-1559.

O’Brien, E. P.‡; Moyna, G., "Use of ¹³C Chemical Shift Surfaces in the Study of Carbohydrate Conformation Application to Cyclomaltooligosaccharides (Cyclodextrins) in the Solid State and in Solution", Carbohydrate Res. 2004, 339, 87-96.

Zauhar, R. J.; Moyna, G.; Tian. L.-F.*; Li, Z.-J.*; Welsh, W. J., "Shape Signatures, a New Approach to Computer-Aided Ligand- and Receptor-Based Drug Design", J. Med. Chem. 2003, 46, 5674-5690.

Ren, H.*; Grady, S.‡; Banghart, M.‡; Moulthrop, J. S.‡; Kendrick, H.; Yardley, V.; Croft, S. L.; Moyna, G., "Synthesis and In Vitro Protozoocidal Activity of a Series of Benzotropolone Derivatives Incorporating Endocyclic Hydrazines", Eur. J. Med. Chem. 2003, 38, 949-957.

Swalina, C. W.‡; O'Brien, E. P.‡; Moyna, G., "A Study of the Temperature-Dependent Conformational Averaging of ¹H-NMR Resonances in Vinylcyclopropane Through the Use of Ab Initio Methodology and Boltzmann Statistics", Magn. Reson. Chem. 2002, 40, 195-201.

Swalina, C. W.‡; Zauhar, R. J.; DeGrazia, M. J.‡; Moyna, G., "Derivation of ¹³C Chemical Shift Surfaces for the Anomeric Carbons of Oligosaccharides and Glycopeptides Using Ab Initio Methodology", J. Biomolec. NMR 2001, 21, 49-61.