Evaluation of an optically active crown ether for the chiral separation of di- and tripeptides.
Evaluation of an optically active crown ether for the chiral separation of di- and tripeptides.
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评估用于二肽和三肽手性分离的光学活性冠醚。
DOI：
10.1016/0021-9673(95)00371-s
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发表时间：
1995
影响因子：
4.1
通讯作者：
K. Wiesmüller
中科院分区：
文献类型：
--
作者：
R. Kuhn;D. Riester;B. Fleckenstein;K. Wiesmüller
采用对映选择性冠醚作为缓冲添加剂，通过毛细管区带电泳实现了许多二肽和三肽的直接光学分辨。质子化的伯胺与冠醚形成包合物。手性拆分基于非对映体配合物的不同稳定性常数，从而改变对映体的电泳迁移率。对映体选择性受胺官能团与手性碳原子之间距离的强烈影响。用专门为此目的合成的二肽和三肽研究了这种效应。一般来说，对于那些胺基位于距离立体中心4个键远的肽，基线分辨率得到了。此外，分离了具有两个手性中心的三肽，以研究手性选择器分析具有相关结构的复杂分析物的潜力。冠醚浓度、缓冲液pH和温度等实验因素也对分辨率有较大影响。这些因素可以成功地用于方法优化。
The direct optical resolution of a number of di- and tripeptides was achieved by capillary zone electrophoresis using an enantioselective crown ether as buffer additive. The protonated primary amines form inclusion complexes with the crown ether. Chiral resolution is based on different stability constants of the diastereomeric complexes thereby changing the electrophoretic mobilities of the enantiomers. Enantioselectivity is strongly affected by the distance between the amine functionality and the chiral carbon atom. This effect was studied using di- and tripeptides especially synthesized for this purpose. In general, baseline resolution was obtained for those peptides with the amine group located as far as four bonds from the stereogenic center. Additionally, tripeptides possessing two chiral centers were separated to investigate the potential of the chiral selector for the analysis of complex analytes with related structures. Experimental factors such as crown ether concentration, buffer pH and temperature also show a strong influence on the resolution. These factors can be successfully employed for method optimization.