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Contacts between aromatic surfaces and saccharide CH groups are common motifs in natural carbohydrate recognition. These CH-pi interactions are modeled in "synthetic lectins" which employ oligophenyl units as apolar surfaces. Here we report the synthesis and study of new synthetic lectins with fluoro- and hydroxy-substituted biphenyl units, designed to explore the role of pi-electron density in carbohydrate CH-pi interactions. We find evidence that recognition can be moderated through electronic effects but that other factors such as cavity hydration are also important and sometimes predominant in determining binding strengths.
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- 1 Finished
1/06/06 → 1/08/09