64343-40-4Relevant academic research and scientific papers
Chiral recognition in cucurbituril cavities
Rekharsky, Mikhail V.,Yamamura, Hatsuo,Inoue, Chika,Kawai, Masao,Osaka, Issey,Arakawa, Ryuichi,Shiba, Kouhei,Sato, Akihiro,Young, Ho Ko,Selvapalam, Narayanan,Kim, Kimoon,Inoue, Yoshihisa
, p. 14871 - 14880 (2006)
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+.
