以羟丙基-β-环糊精为手性添加剂拆分2-取代芳基丙酸:取代基对手性识别的影响（英文）

以羟丙基-β-环糊精为手性添加剂,采用反相高效液相色谱法对2-取代芳基丙酸类物质进行了手性拆分。考察了流动相的组成,包括缓冲溶液、有机改性剂以及添加剂的浓度等。缓冲溶液的pH值、有机改性剂的种类与浓度,以及添加剂的浓度对色谱峰的保留时间和分离度均有较大的影响。以YMC ODS-C_(18)(150 mm×4.6 mm,5μm)为色谱柱,乙腈-0.10 mol/L磷酸盐缓冲液(pH 3.3,含25 mmol/L添加剂)为流动相,测定了各2-取代芳基丙酸与羟丙基-β-环糊精的包结常数,考察了羟丙基-β-环糊精对各物质的包结形式。实验结果表明,羟丙基-β-环糊精与各对映体均以1∶1的形式包结,同时发现推电子取代基更有利于羟丙基-β-环糊精的包结行为,为羟丙基-β-环糊精对手性拆分的影响提供了一个有利的参考因素。

Enantioseparation of 2-(substituted phenyl) propanoic acids with hydroxypropyl-β-cyclodextrin as a chiral additive:investigation of substituent influence on enantiorecognition

2-(Substituted phenyl) propanoic acids were successfully enantioseparated by reversed-phase high-performance liquid chromatography with hydroxypropyl-β-cyclodextrin as a mobile phase additive.The effect of the mobile phase composition,including the aqueous buffer,the organic modifier,and the concentration of the additive,were investigated.The aqueous buffer pH,the type and percentage of the organic modifier,and the additive concentration had a great influence on the retention time and peak resolution.Enantioseparations were achieved on an YMC ODS-C₁₈(150 mm×4.6 mm,5 μm) column.The mobile phase was composed of acetoni-trile and 0.10 mol/L of phosphate buffer at pH 3.3 containing 25 mmol/L of the hydroxypropyl-β-cyclodextrin additive.The binding constants of the inclusion complex between each of the 2-(substituted phenyl) propanoic acids and hydroxypropyl-β-cyclodextrin were determined,and the formation of the inclusion complex was investigated.The results showed that the stoichiometries for all of the inclusion complexes between hydroxypropyl-β-cyclodextrin and enantiomers were 1:1.It was found that the electron-donating group of the enantiomer was advantageous for enantiorecognition by hydroxypropyl-β-cyclodextrin.The results provide a useful reference for the influence of the enantiorecognitionfactors produced by hydroxypropyl-β-cyclodextrin.Key words:enantioseparation;high-performance liquid chromatography (HPLC);2-(substituted phenyl) pro-panoic acids;hydroxypropyl-β-cyclodextrin