Novel methoxypropylimmidazolium beta-cyclodextrin for improved enantioseparation of amino acids

作者：Tang Jian; Lu Yingying; Wang Yiying; Zhou Jie; Tang Weihua^*

来源：Talanta, 2014, 128: 460-465.

DOI：10.1016/j.talanta.2014.06.006

• Cationic cyclodextrin
• Single-isomer cyclodextrin
• Chiral separation
• Binding constant

A new single-isomer cationic cyclodextrin, mono-6(A)-[3-(3-methoxypropypl)imidazol-1-ium]-6(A)-beta-cyclodextrin chloride, has been synthesized and successfully used for the chiral separation of dansyl amino acids in capillary electrophoresis. With methoxy functionality, the new cationic cyclodextrin exhibits significantly improved enantioselectivities. Excellent enantioseparations for amino acids are obtained in chiral selector concentration range between 2.5 mM to 15 mM at pH 6.0. Chiral resolution as high as 73 was achieved for Dns-Aca with 5 mM chiral selector. Comparison study and theoretical calculation with Wren's model attribute the enhanced enantioseparation to the stronger inclusion complexation between amino acids and cyclodextrin. The binding constants for dansyl amino acids and the cationic cyclodextrins are calculated to be 173-253 M-1, while the optimum cyclodextrin concentrations were estimated to be 4.1-7.6 mM.

• 出版日期2014-10-1
• 单位南京理工大学