Enhanced chiral recognition by cyclodextrin dimers |
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Authors: | Voskuhl Jens Schaepe Kira Ravoo Bart Jan |
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Affiliation: | Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, Münster 48149, Germany; E-Mails: (J.V.); (K.S.) |
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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. |
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Keywords: | cyclodextrins chiral recognition host-guest complexes isothermal titration calorimetry multivalency |
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