Separation of asymmetric triacylglycerols into their enantiomers by recycle high‐performance liquid chromatography

Abstract

AbstractA recycle HPLC system equipped with a polysaccharide‐based chiral column was used for the enantiomeric separation of asymmetric triacylglycerols (TAGs). When the chiral columns were screened by the resolution of 1,2‐dipalmitoyl‐3‐oleoyl‐rac‐glycerol separation was achieved only with the cellulose tris‐ (3,5‐dimethylphenylcarbamate) chiral selector. The resolution of other TAG enantiomers was also examined, and 1,2‐dioleoyl‐3‐palmitoyl‐rac‐glycerol, 1,2‐dipalmitoyl‐3‐linoleoyl‐rac‐glycerol, 1,2‐dipalmitoyl‐3‐eicosapentaenoyl‐rac‐glycerol, 1,2‐dipalmitoyl‐3‐docosahexaenoyl‐rac‐glycerol, and 1,2‐docosahexaenoyl‐3‐palmitoyl‐rac‐glycerol were resolved into their respective enantiomers. However, neither 1,2‐dioleoyl‐3‐linoleoyl‐rac‐glycerol, consisting of only unsaturated fatty acids, nor 1,2‐dipalmitoyl‐3‐stearoyl‐rac‐glycerol, consisting of only saturated fatty acids, was resolved. In addition, 1,2‐eicosapentaenoyl‐3‐palmitoyl‐rac‐glycerol was not resolved clearly, even in the recycle runs. These results suggest that asymmetric TAGs having both a palmitic acid moiety and an unsaturated fatty acid moiety at the sn‐1 or sn‐3 positions might be resolved on a cellulose tris‐ (3,5‐dimethylphenylcarbamate) chiral column.