A Carbohydrate-Conjugated Deep Cavitand Permits Observation of Caviplexes in Human Serum

A deep cavitand was covalently modified with carbohydrates to provide solubility in biologically relevant environments and to investigate its receptor function. Specifically, a tetrakis(β-d-glucosyl) cavitand (1) that was soluble in neutral water or acid/base-buffered solutions was synthesized, and...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 133; no. 49; pp. 19653 - 19655
Main Authors Ryan, Daniel A, Rebek, Julius
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.12.2011
Amer Chemical Soc
Subjects
Carbohydrates - chemistry
Chemistry
Chemistry, Multidisciplinary
Ethers, Cyclic - chemistry
Humans
Magnetic Resonance Spectroscopy
Micelles
Models, Molecular
Physical Sciences
Resorcinols - chemistry
Science & Technology
Serum - chemistry
Solubility
CATALYSIS
RECOGNITION
RESORCINOL CYCLIC TETRAMER
WATER-SOLUBLE CAVITANDS
2-DIMENSIONAL NMR
GUEST
TERMINAL ALKYNES
HOST
MEMBRANE-PROTEINS
COMPLEXATION
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Summary:A deep cavitand was covalently modified with carbohydrates to provide solubility in biologically relevant environments and to investigate its receptor function. Specifically, a tetrakis(β-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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja2055676