Capillary electrophoretic separation of binaphthyl enantiomers with two polymeric chiral surfactants:: 1H-nuclear magnetic resonance and fluorescence spectroscopy study
Capillary electrophoretic separation of binaphthyl enantiomers with two polymeric chiral surfactants:: 1H-nuclear magnetic resonance and fluorescence spectroscopy study
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DOI：
10.1002/1522-2683(20000601)21:10
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发表时间：
2000-06-01
期刊：
影响因子：
2.9
通讯作者：
Warner, IM
中科院分区：
文献类型：
--
作者：
Yarabe, HH;Rugutt, JK;Warner, IM
以水溶性高分子手性表面活性剂（PCS）、N-十一酰-L-缬氨酸钠（poly-L-SUV）和十一酰-L-异亮氨酸钠（poly-L-SUI）为缓冲添加剂，在电动色谱（EKC）中分离了2，2 ′-二羟基-1，1 ′-联萘（BOH）和1，1 ′-联萘-2，2 ′-磷酸氢二酯（BNP）的外消旋混合物。通过H-1-NMR滴定法和荧光光谱法分别测定了PCS与BNP和BOH对映体的表观结合常数。1H-1-NMR滴定研究表明，BNP对映体位于PCS的疏水胶束口袋中，并形成1：1化学计量比的复合物。从Benesi-Hildebrand处理的荧光数据的BOH的PCS的结合常数测定。的EKC数据证实的结合常数，支持包合物的形成。根据H-1-NMR数据中观察到的分子间相互作用，提出了一个合理化BNP对映体手性鉴别的模型。
The use of the water-soluble polymeric chiral surfactants (PCS), sodium N-undecanoyl-L-valinate (poly-L-SUV) and sodium undecanoyl-L-isoleucinate (poly-L-SUI) as buffer additives in electrokinetic chromatography (EKC) afforded the separation of racemic mixtures of 2,2'-dihydroxy-1,1'-binaphthyl (BOH) and 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (BNP). The apparent binding constants of the PCS to the enantiomers of BNP and BOH were obtained through H-1-nuclear magnetic resonance (H-1-NMR) titrations and fluorescence spectroscopy, respectively. The H-1-NMR titration studies show that the BNP enantiomers are localized in the hydrophobic micellar pockets of PCS and form complexes of a 1:1 stoichiometry. The binding constants of PCS of BOH were determined from a Benesi-Hildebrand treatment of the fluorescence data. The EKC data corroborate those of the binding constants, supporting the formation of inclusion complexes. A model rationalizing the chiral discrimination of the enantiomers of BNP is proposed based on the intermolecular interactions observed in H-1-NMR data.