In situ synthesis of di-n-butyl l-tartrate-boric acid complex chiral selector and its application in chiral microemulsion electrokinetic chromatography.
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 beta-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.
National Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
Shaoqiang
S
Hu
Yonglei
Y
Chen
Huadong
H
Zhu
Jinhua
J
Zhu
Na
N
Yan
Xingguo
X
Chen
D000319:Adrenergic beta-Antagonists / Q000737:chemistry; D001888:Boric Acids / Q000138:chemical synthesis / Q000737:chemistry*; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000295:instrumentation* / Q000379:methods*; D013237:Stereoisomerism; D013644:Tartrates / Q000138:chemical synthesis / Q000737:chemistry*
D000319:Adrenergic beta-Antagonists; D001888:Boric Acids; D013644:Tartrates; C522497:dibutyl tartrate; C032688:boric acid