Zhang Zhen-Bin, Zhang Wei-Guang, Luo Wen-Jun, Fan Jun
School of Chemistry & Environment, South China Normal University, GuangZhou 510006, China.
J Chromatogr A. 2008 Dec 12;1213(2):162-8. doi: 10.1016/j.chroma.2008.10.038. Epub 2008 Oct 17.
A novel cyclodextrin (CD) derivative-mono (6(A)-azido-6(A)-deoxy)-per(p-chlorophenylcarbamoylated) beta-CD was synthesized and chemically immobilized onto the surface of amino-functionalized silica gel to afford a structurally well-defined chiral stationary phase (CSP) for high performance liquid chromatography (HPLC). The p-chlorophenyl groups introduced on the beta-CD are pi-electron deficient (i.e., pi-acidic moieties); therefore the stronger pi-pi interaction which plays an important role in chiral recognition process is expected between aromatic analytes and this type of the CSP. The enantiomeric separations of 11 piperazine derivatives as well as six racemates have been successfully achieved on this CSP in the normal and reversed phase modes.
合成了一种新型环糊精（CD）衍生物——单（6(A)-叠氮基-6(A)-脱氧）-全（对氯苯基氨基甲酰化）β-环糊精，并将其化学固定在氨基功能化硅胶表面，以提供一种结构明确的用于高效液相色谱（HPLC）的手性固定相（CSP）。引入到β-环糊精上的对氯苯基是缺π电子的（即π-酸性部分）；因此，预计在芳香族分析物与这种类型的CSP之间会存在在手性识别过程中起重要作用的更强的π-π相互作用。在该CSP上，以正相和反相模式成功实现了11种哌嗪衍生物以及6种外消旋体的对映体分离。
