Achievement of enantioselectivity of non-polar primary amines by a non-chiral crown ether
Achievement of enantioselectivity of non-polar primary amines by a non-chiral crown ether
复制标题
非手性冠醚实现非极性伯胺的对映选择性
DOI：
10.1016/s0021-9673(97)00541-4
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发表时间：
1997
影响因子：
4.1
通讯作者：
R. Vivilecchia
中科院分区：
文献类型：
--
作者：
Wei Huang;S. Fazio;R. Vivilecchia
A non-chiral crown ether (18-crown-6), as a molecular modifier, along with cyclodextrin (CD) was used to achieve or enhance enantioselective separations of non-polar primary amines in capillary electrophoresis. Chiral separations of the primary amines are rarely achieved using cyclodextrins alone in capillary electrophoresis, because the three-point intermolecular interaction between the chiral amine and the cyclodextrin is not selective enough to yield resolution of the enantiomers of interest. To resolve these types of compounds, the non-chiral crown ether (18-crown-6) has been used with cyclodextrins (CDs) in the buffer. In the method, the amino group of the compounds is protonated using a low pH buffer solution and locked into 18-crown-6 ring forming a host-guest complex (amine+18-crown-6). The hydrophobic portion of the complex is then incorporated into the cavity of the cyclodextrin forming a secondary sandwich complex (18-crown-6+ amine+CD), in which the chiral center of the amine molecule is recognized. It is postulated that the sandwich complex results in a more rigid structure around the chiral center and more selective interaction between the chiral amine and cyclodextrin. This method can be used to separate a variety of non-polar primary amines, even when the chiral center is three-carbon atoms or more from the hydrophobic group.
影响因子：
7.4
作者：
K. Gahm;A. Stalcup
通讯作者：
K. Gahm;A. Stalcup
影响因子：
7.4
作者：
ARMSTRONG, DW;RUNDLETT, K;REID, GL
通讯作者：
REID, GL