Chiral Recognition in Cucurbituril Cavities

Autor:	Issey Osaka, Kouhei Shiba, Masao Kawai, Ryuichi Arakawa, Akihiro Sato, Chika Inoue, Mikhail V. Rekharsky, Yoshihisa Inoue, Hatsuo Yamamura, Kimoon Kim, Narayanan Selvapalam, Young Ho Ko
Rok vydání:	2006
Předmět:	Aqueous solution Dipeptide Chemistry Stereochemistry Supramolecular chemistry Diastereomer General Chemistry Biochemistry Catalysis Inclusion compound chemistry.chemical_compound Colloid and Surface Chemistry Molecular recognition Cucurbituril Enantiomer
Zdroj:	Journal of the American Chemical Society. 128:14871-14880
ISSN:	1520-5126 0002-7863
Popis:	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+.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6ef4a1fb6b445f5bb94754e20e5f4297 https://doi.org/10.1021/ja063323p Zobrazit plný text záznamu