Application of sulfated cyclodextrins to chiral separations by capillary zone electrophoresis.
Application of sulfated cyclodextrins to chiral separations by capillary zone electrophoresis.
复制标题
硫酸化环糊精在毛细管区带电泳手性分离中的应用。
DOI：
10.1021/ac950764a
复制
发表时间：
1996
影响因子：
7.4
通讯作者：
Gahm,KH
中科院分区：
文献类型：
--
作者：
Stalcup,AM;Gahm,KH
随机取代的硫酸化环糊精（取代度，〜7−10）的混合物成功地用作手性添加剂，用于 56 种具有药用价值的化合物的对映体分离，包括麻醉剂、抗心律失常药、抗抑郁药、抗惊厥药、抗组胺药、抗高血压药、抗疟药、松弛剂和支气管扩张剂。分离在 pH 3.8 下完成，阳极位于色谱柱的检测器端。在这些条件下，其中电渗流朝向柱的注射端并且带负电的环糊精的电泳迁移率朝向检测器，在不存在硫酸化环糊精的情况下没有分析物到达检测器。大多数（40）成功解析的对映体含有基本官能团和立体碳。然而，这种硫酸化环糊精添加剂的多功能性也通过以下事实得到了证明：三种阻转异构体、1,1'-联萘-2,2'-磷酸氢二酯、1,1'-联萘-2,2'-二醇和 Troger 碱以及几种中性分析物在这些条件下也成功对映体拆分。分离机制似乎涉及包合络合。
Mixtures of randomly substituted sulfated cyclodextrins (degree of substitution, ∼7−10) were successfully used as chiral additives for the enantioseparation of 56 compounds of pharmaceutical interest, including anesthetics, antiarrhythmics, antidepressants, anticonvulsants, antihistamines, antihypertensives, antimalarials, relaxants, and bronchodilators. The separations were accomplished at pH 3.8, with the anode at the detector end of the column. Under these conditions, in which electroosmotic flow is directed toward the injection end of the column and the electrophoretic mobility of the negatively charged cyclodextrin is toward the detector, none of the analytes reached the detector in the absence of the sulfated cyclodextrin. Most (40) of the successfully resolved enantiomers contained basic functionality and a stereogenic carbon. However, the versatility of this sulfated cyclodextrin additive was also demonstrated by the fact that three atropisomers, 1,1‘-binaphthyl-2,2‘-diyl hydrogen phosphate, 1,1‘-binaphthyl-2,2‘-diol, and Troger's base, and several neutral analytes were also successfully enantioresolved under these conditions. The separation mechanism seems to involve inclusion complexation.