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Citation: WANG Xiaoping, LU Mengxia, BU Zhisi, LÜ Liqiong, TONG Shengqiang. Enantioseparation of 2-(substituted phenyl) propanoic acids with hydroxypropyl-β-cyclodextrin as a chiral additive:investigation of substituent influence on enantiorecognition[J]. Chinese Journal of Chromatography, ;2017, 35(5): 544-550. doi: 10.3724/SP.J.1123.2016.12020 shu

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

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, China

Received Date: 9 December 2016

Fund Project: Project of Department of Education of Zhejiang Province,China (No.pd2013031).

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
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