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Enhanced Chiral Recognition by Cyclodextrin Dimers
Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, Münster 48149, Germany
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Received: 16 June 2011; in revised form: 7 July 2011 / Accepted: 8 July 2011 / Published: 18 July 2011
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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Voskuhl, J.; Schaepe, K.; Ravoo, B.J. Enhanced Chiral Recognition by Cyclodextrin Dimers. Int. J. Mol. Sci. 2011, 12, 4637-4646.
Voskuhl J, Schaepe K, Ravoo BJ. Enhanced Chiral Recognition by Cyclodextrin Dimers. International Journal of Molecular Sciences. 2011; 12(7):4637-4646.
Voskuhl, Jens; Schaepe, Kira; Ravoo, Bart Jan. 2011. "Enhanced Chiral Recognition by Cyclodextrin Dimers." Int. J. Mol. Sci. 12, no. 7: 4637-4646.