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