Liquid chromatographic separation of enantiomers of beta-amino acids using a chiral stationary phase.
The enantiomers of both alpha-substituted beta-alanines and beta-substituted beta-alanines may be chromatographically separated using silica-bonded chiral stationary phases derived from N-acetylated alpha-arylalkylamines. The amino acids are chromatographed as alkyl esters of N-3,5-dinitrobenzoyl derivatives; separability factors range from 1.11 to 1.65 for nine alpha-substituted beta-alanines and from 1.08 to 1.20 for nine beta-substituted beta-alanines. The enantiomers of beta-aminoisobutyrate and beta-leucine, chiral beta-amino acids occurring in animal tissues and physiological fluids, are among those resolved. The enantiomers of R,S-beta-aminoisobutyrate and several related alpha-alkyl-beta-alanines were prepared by chromatographic resolution of diastereomeric dipeptides.
D000596:Amino Acids / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D006868:Hydrolysis; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000596:Amino Acids