Chiral recognition in cucurbituril cavities

Abstract

For the first time, achiral cucurbiturils (CBs) were endowed with significant enantiomeric and distereomeric discrimination by incorporating a strong chiral binder. Calorimetric, nuclear magnetic, light-scattering, and mass spectral studies revealed that (S)-2-methylbutylamine (as a strong binder) can be discriminated by two enantiomeric supramolecular hosts, composed of CB[6] and (R)- or (S)-2-methylpiperazine, with an unprecedented 95% enantioselectivity in aqueous NaCl solution. This is the highest enantioselectivity ever reported for a supramolecular system derived from an achiral host. Similarly, CB[7], with a larger cavity, exhibited diastereoselectivities up to 8 times higher for diastereomeric dipeptides, as demonstrated for L-Phe-L-Leu-NH3+ versus L-Phe-D-Leu-NH3+.