Enantiomer separation by countercurrent chromatography using cinchona alkaloid derivatives as chiral selectors

被引:53
|
作者
Franco, P
Blanc, J
Oberleitner, WR
Maier, NM
Lindner, W
Minguillón, C
机构
[1] Univ Barcelona, Fac Farm, Quim Farmaceut Lab, E-08028 Barcelona, Spain
[2] Univ Vienna, Inst Analyt Chem, A-1090 Vienna, Austria
关键词
D O I
10.1021/ac020209q
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Cinchona-derived anion-exchange-type chiral selectors have been adapted and employed in countercurrent chromatography (CCC) for the separation of enantiomers of N-derivatized amino acids and 2-aryloxypropionic acids. The accurate optimization of the enantioseparation in terms of solvent system composition, pH values, ionic strength, and CCC operating conditions was performed. A wide range of solvent mixtures was evaluated. Successful resolutions were achieved in systems such as ammonium acetate buffer/tert-amyl alcohol/methanol/heptane and especially ammonium acetate buffer/methyl isobutyl ketone or diisopropyl ether. Up to 300 mg (0.92 mmol) of N-(3,5-dinitrobenzoyl)-(+/-)-leucine was totally resolved in a single run using a 10 mM concentration of chiral selector in 122 mL of stationaty phase. This amount could be increased up to 900 mg (2.77 mmol) when pH-zone-refining mode was applied. The results here presented account for the high potential of CCC As a preparative enantiomer separation technique.
引用
收藏
页码:4175 / 4183
页数:9
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