Dendrimer folding in aqueous media: An example of solvent-mediated chirality switching

ORGN 455

Jon R. Parquette,, Department of Chemistry, Ohio State University, 100 West 18th Avenue, Columbus, OH 43210 and Amanda L. Hofacker, Chemistry, Ohio State University, 100 W. 18th avenue, Columbus, OH 43210.
Investigation of allosterism, structural cooperativity, correlated motions, and dynamic equilibrium has been performed through the study of synthetic pyridine-2,6-dicarboxamide dendritic molecules. First-, second-, and third-generation chiral water-soluble pentaethylene glycol dendritic structures develop stable secondary conformations in both aqueous and organic media as indicated by circular dichroism (CD) spectroscopy. Furthermore, the second-, and third-generation dendrons exhibit conformational change from an M to a P helical bias upon addition of water to a THF solution. With this allosteric control in synthetic compounds, it becomes possible that secondary structures can be designed to perform specific functions upon activation. Further studies of non-symmetrical dendritic structures consisting of chiral and achiral terminal groups, enantiomeric terminal groups, as well as mixtures of chiral and achiral compounds, and enantiomeric compounds have been studied to further investigate the Sergeants and Soldiers, and Majority Rules principles.


Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005