High-performance liquid chromatographic enantioseparation of isopulegol-based beta-amino lactone and beta-amino amide analogs on polysaccharide-based chiral stationary phases focusing on the change of the enantiomer elution order

摘要

The enantioselective separation of newly prepared, pharmacologically significant isopulegol-based amino lactones and beta-amino amides has been studied by carrying out high-performance liquid chromatography on diverse amylose and cellulose tris-(phenylcarbamate)-based chiral stationary phases (CSPs) in n-hexane/alcohol/diethylamine or n-heptane/alcohol/ diethylamine mobile phase systems. For the elucidation of mechanistic details of the chiral recognition, seven polysaccharide-based CSPs were employed under normal-phase conditions. The effect of the nature of selector backbone (amylose or cellulose) and the position of substituents of the tris-(phenylcarbamate) moiety was evaluated. Due to the complex structure and solvation state of polysaccharide-based selectors and the resulting enantioselective interaction sites, the chromatographic conditions (e.g., the nature and content of alcohol modifier) were found to exert a strong influence on the chiral recognition process, resulting in a particular elution order of the resolved enantiomers. Since no prediction can be made for the observed enantiomeric resolution, special attention has been paid to the identification of the elution sequences.