RESOLUTION OF RACEMIC γ-SUBSTITUTED BUTENOLIDE DERIVATIVES USING A POLYSACCHARIDE TYPE STATIONARY PHASE BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY

The enantioseparation by immobilized polysaccharide-based chiral stationary phases has pronounced advantages due to its enhanced efficiency and universal solvent resistance. The newly synthesized γ-substituted butenolide derivatives, which showed good inhibitory activity against wide range of fungi, were successfully resolved on cellulose tris(3,5-dichlorophenylcarbamate) chiral stationary phase (Chiralpak IC) by high performance liquid chromatography (HPLC). The effects of mobile phase composition and column temperature were studied. The good resolution was achieved using a mobile phase composition of hexane and ethanol. Under optimal conditions, the resolutions of enantiomers of five compounds were 1.96, 1.66, 1.93, 1.72, and 2.03, respectively. For the butenolides derivatives, π–π interaction contributes to the retention rather than selectivity, resolution was dramatically changed corresponding to variation of ethanol content in the mobile phase. This suggests that the dominant chiral recognition is fr...