Chiral recognition in cucurbituril cavities
Chiral recognition in cucurbituril cavities
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DOI：
10.1021/ja063323p
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发表时间：
2006-11-22
影响因子：
15
通讯作者：
Inoue, Yoshihisa
中科院分区：
文献类型：
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作者：
Rekharsky, Mikhail V.;Yamamura, Hatsuo;Inoue, Yoshihisa
通过引入强手性粘合剂，非手性葫芦脲（CB）首次被赋予了显着的对映体和非立体异构体歧视。量热、核磁、光散射和质谱研究表明，（S）-2-甲基丁胺（作为强粘合剂）可以被CB[6]和（R）-或（S）-2-甲基哌嗪组成的两种对映体超分子主体区分，在NaCl水溶液中具有前所未有的95%对映体选择性。这是有史以来报道的最高的对映体选择性的超分子系统来自非手性主机。类似地，具有较大空腔的CB[7]对于非对映体二肽表现出高达8倍的非对映体选择性，如L-Phe-L-Leu-NH3+与L-Phe-D-Leu-NH3+所证明的。
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+.