Dress-up chiral columns for the enantioseparation of amino acids based on fluorous separation

作者：Todoroki Kenichiro; Ishii Yasuhiro; Toyoda Koji; Ikawa Takashi; Min Jun Zhe; Inoue Koichi; Akai Shuji; Toyo' oka Toshimasa

来源：Analytical and Bioanalytical Chemistry, 2013, 405(25): 8121-8129.

DOI：10.1007/s00216-013-7207-4

• Amino acids
• Peptides
• HPLC
• Chiral analysis

In this paper, we report a new type of chiral high-performance liquid chromatography (HPLC) column-a so-called dress-up chiral column-featuring a chiral stationary phase adsorbed reversibly in a commercial fluorous HPLC column through fluorous interactions. We synthesized perfluroalkylated proline derivatives as chiral stationary phase compounds and then adsorbed them reversibly in the fluorous HPLC column through the pumping of their solutions. By using this dress-up chiral column and fluorophobic elution of an aqueous copper(II) sulfate/MeOH mixture, we could enantioseparate seven racemic amino acids within 40 min. When we washed the dress-up chiral column with fluorophilic tetrahydrofuran or MeOH, the adsorbed chiral stationary phase compounds desorbed from the column, completely destroying its enantioseparation ability. The relative standard deviation of the retention times, the number of theoretical plates, and the resolution for each of four preparations of the dress-up columns were all less than or equal to 9.53 % in 20-times repeated analysis, and were all less than or equal to 18.7 % in four different preparations, respectively.

• 出版日期2013-10