Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 49, Pages 19653-19655Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2055676
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Funding
- Defense Threat Reduction Agency-Joint Science and Technology Office, Translational Medical ST Division
- NSF [CHE 1037590]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1037590] Funding Source: National Science Foundation
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A deep cavitand was covalently modified with carbohydrates to provide solubility in biologically relevant environments and to investigate its receptor function. Specifically, a tetrakis(beta-D-glucosyl) cavitand (1) that was soluble in neutral water or acid/base-buffered solutions was synthesized, and it formed complexes with hydrophobic small molecules. Extraction of the cavitand into aqueous sodium dodecyl sulfate micelles as simple membrane mimetics increased the scope of guests bound by 1 beyond that observed in only aqueous media. Complex formation was also detected in human serum. The findings show the functional compatibility of the receptor in both micelle-bound and serum-soluble forms.
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