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Enhanced chiral recognition by cyclodextrin dimers.

ABSTRACT: In this article we investigate the effect of multivalency in chiral recognition. To this end, we measured the host-guest interaction of a ?-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 ?-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.

SUBMITTER: Voskuhl J

PROVIDER: S-EPMC3155374 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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Enhanced chiral recognition by cyclodextrin dimers.

Voskuhl Jens J Schaepe Kira K Ravoo Bart Jan BJ

International journal of molecular sciences 20110718 7

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 ...[more]

PMID: 21845101

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