ORGN 745 |
| Several lines of evidence in biological systems suggest that buried electrostatic and hydrogen bonding interactions are more favorable in the hydrophobic microenvironment of a biological macromolecule relative to the surrounding aqueous medium. Yet, there have been surprisingly few synthetic systems that have explored this phenomenon as a strategy for molecular recognition in water. Introverted carboxylic acid substituents have previously been incorporated into cavitand receptors in our laboratory, allowing buried acid-base interactions to form with amine guests in organic solvents. In this report, we extend this system to water-soluble cavitand 1 in order to bind positively charged guests through a partially solvent-excluded electrostatic interaction in water. The synthesis and conformational studies of cavitand 1, as well its binding properties for amine guests will be presented.
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Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
