In situsynthesis of di-n-butyll-tartrate–boric acid complex chiral selector and its application in chiral microemulsion electrokinetic chromatography

Shaoqiang Hu, Yonglei Chen, Huadong Zhu, Jinhua Zhu, Na Yan, Xingguo Chen, Shaoqiang Hu, Yonglei Chen, Huadong Zhu, Jinhua Zhu, Na Yan, Xingguo Chen

Index: J. Chromatogr. A. 1216(45) , 7932-40, (2009)

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Abstract

A novel procedure for in situ assembling a complex chiral selector, di- n-butyl l-tartrate–boric acid complex, by the reaction of di- n-butyl l-tartrate with boric acid in a running buffer was reported and its application in the enantioseparation of β-blockers and structural related compounds by chiral microemulsion electrokinetic chromatography (MEEKC) has been demonstrated. In order to achieve a good enantioseparation, the effect of dibutyl l-tartrate and sodium tetraborate concentration, surfactant identity and concentration, cosurfactant, buffer pH and composition, organic modifiers, as well as applied voltage and capillary length were investigated. Ten pairs of enantiomers that could not be separated with only dibutyl l-tartrate, obtained good chiral separation using the complex chiral selector; among them, seven pairs could be baseline resolved under optimized experimental conditions. The fixation of chiral centers by the formation of five-membered rings, and being oppositely charged with basic analytes were thought to be the key factors giving the complex chiral selector a superior chiral recognition capability. The effect of the molecular structure of analytes on enantioseparation was discussed in terms of molecular interaction.