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• Schaepe, K
• Ravoo, B
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• Schaepe, K
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• Schaepe, K
• Ravoo, B

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Int. J. Mol. Sci. 2011, 12(7), 4637-4646; doi:10.3390/ijms12074637

Article

Enhanced Chiral Recognition by Cyclodextrin Dimers

Jens Voskuhl, Kira Schaepe and Bart Jan Ravoo*

Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, Münster 48149, Germany

* Author to whom correspondence should be addressed.

Received: 16 June 2011; in revised form: 7 July 2011 / Accepted: 8 July 2011 / Published: 18 July 2011

(This article belongs to the Special Issue Molecular Self-Assembly 2011)

Download PDF Full-Text [1024 KB, uploaded 18 July 2011 16:21 CEST]

Abstract: In this article we investigate the effect of multivalency in chiral recognition. To this end, we measured the host-guest interaction of a β-cyclodextrin dimer with divalent chiral guests. We report the synthesis of carbohydrate-based water soluble chiral guests functionalized with two borneol, menthol, or isopinocampheol units in either (+) or (–) configuration. We determined the interaction of these divalent guests with a β-cyclodextrin dimer using isothermal titration calorimetry. It was found that—in spite of a highly unfavorable conformation—the cyclodextrin dimer binds to guest dimers with an increased enantioselectivity, which clearly reflects the effect of multivalency.

Keywords: cyclodextrins; chiral recognition; host-guest complexes; isothermal titration calorimetry; multivalency

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