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

Enhanced Chiral Recognition by Cyclodextrin Dimers

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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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

Voskuhl, J.; Schaepe, K.; Ravoo, B.J. Enhanced Chiral Recognition by Cyclodextrin Dimers. Int. J. Mol. Sci. 2011, 12, 4637-4646.

AMA Style

Voskuhl J, Schaepe K, Ravoo BJ. Enhanced Chiral Recognition by Cyclodextrin Dimers. International Journal of Molecular Sciences. 2011; 12(7):4637-4646.

Chicago/Turabian Style

Voskuhl, Jens; Schaepe, Kira; Ravoo, Bart Jan. 2011. "Enhanced Chiral Recognition by Cyclodextrin Dimers." Int. J. Mol. Sci. 12, no. 7: 4637-4646.

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