Enhanced Chiral Recognition by Cyclodextrin Dimers

International Journal of Molecular Sciences

Jens Voskuhl¹  Kira Schaepe¹ 

[1] Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, Münster 48149, Germany;

关键词: cyclodextrins;    chiral recognition;    host-guest complexes;    isothermal titration calorimetry;    multivalency;   

DOI  :  10.3390/ijms12074637

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2011 by the authors; licensee MDPI, Basel, Switzerland.