title: 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 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.
authors.affiliation: Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, Münster 48149, Germany; E-Mails: jens.voskuhl@uni-muenster.de (J.V.); k_scha19@uni-muenster.de (K.S.).
authors.forename: Jens
authors.initials: J
authors.lastname: Voskuhl
authors.forename: Kira
authors.initials: K
authors.lastname: Schaepe
authors.forename: Bart Jan
authors.initials: BJ
authors.lastname: Ravoo
mesh_terms: D002151:Calorimetry; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013816:Thermodynamics; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D047392:beta-Cyclodextrins