Preferential Solvation within Hydrophilic Nanocavities and Its Effect on the Folding of Cholate Foldamers

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2007-01-01
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Zhao, Yan
Zhong, Zhenqi
Ryu, Eui-Hyun
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Zhao, Yan
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Chemistry

The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

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Abstract

The conformations of three cholate foldamers and one molecular basket were studied by fluorescence and NMR spectroscopy. In nonpolar solvents (e.g., hexane/ethyl acetate or ethyl acetate) mixed with a small amount of a polar solvent (e.g., alcohol or DMSO), the cholate oligomer folded into a helix with the hydrophilic faces of the cholates turned inward. Folding created a hydrophilic nanocavity preferentially solvated by the entrapped polar solvent concentrated from the bulk. This microphase separation of the polar solvent was critical to the folding process. Folding was favored by larger-sized polar solvent molecules, as fewer such molecules could occupy and solvate the nanocavity, thus requiring a smaller extent of phase separation during folding. Folding was also favored by smaller/acyclic nonpolar solvent molecules, probably because they could avoid contact with the OH/NH groups within the nanocavity better than larger/cyclic nonpolar solvent molecules.

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Reprinted (adapted) with permission from Journal of the American Chemical Society 129 (2007): 218, doi:10.1021/ja0671159. Copyright 2007 American Chemical Society.

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Mon Jan 01 00:00:00 UTC 2007
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