Chiral recognition in cucurbituril cavities
SCIE
SCOPUS
- Title
- Chiral recognition in cucurbituril cavities
- Authors
- Rekharsky, MV; Yamamura, H; Inoue, C; Kawai, M; Osaka, I; Arakawa, R; Shiba, K; Sato, A; Ko, YH; Selvapalam, N; Kim, K; Inoue, Y
- Date Issued
- 2006-11-22
- Publisher
- AMER CHEMICAL SOC
- 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+.
- Keywords
- ION COMPLEXED CUCURBITURIL; GAMMA-CYCLODEXTRIN; SOLDIERS PRINCIPLE; ORGANIC-MOLECULES; BETA-CYCLODEXTRIN; HOST; INCLUSION; THERMODYNAMICS; ENCAPSULATION; SERGEANTS
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/23727
- DOI
- 10.1021/JA063323P
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, no. 46, page. 14871 - 14880, 2006-11-22
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