Separation of fatty acid ester and amide enantiomers by high-performance liquid chromatography on chiral stationary phases.
The enantiomeric resolution of a series of chiral fatty acid epoxide and alpha-substituted palmitic acid analogues was examined by high-performance liquid chromatography on chiral stationary phases. The compounds were chromatographed as ester or amide derivatives on commercially available stationary phases that consisted of (R)-N-(3,5-dinitrobenzoyl)phenylglycine either covalently or ionically bonded to aminopropylsilica gel. Factors affecting separation included hydrocarbon chain length of the fatty acid, the type of substituents attached to the chiral center, the type of derivative, and column temperature. Effects of sample size, mobile phase composition, column type, and flow-rate on the resolution and separation factor values were also explored.
Weaner
L E
LE
Department of Chemical Development, McNeil Pharmaceutical, Spring House, PA 19477-0776.
Hoerr
D C
DC
D000577:Amides / Q000032:analysis; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004952:Esters / Q000032:analysis; D005227:Fatty Acids / Q000032:analysis*; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000577:Amides; D004952:Esters; D005227:Fatty Acids; D012997:Solvents