Separation of Underivatised Amino Acid Enantiomers by Means of a Chiral Solvent-Generated Phase

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Abstract
The separation of the enantiomers of underivatised amino acids can be easily realized by reversed-phase chromatography with a chiral eluent. The eluent contains small concentrations of Cu(ll)-L-phenylalanine, N-methyl-, or N,N-dimethyl-L-phenylalanine complexes; the amino acids are separated via diastereomeric complexes by ligand-exchange chromatography. The retention of the amino acids is determined by the equilibrium of ligand-exchange and by hydrophobic interaction. The selectivity is strongly affected by pH value, the proportion of organic modifier, and the ionic strength. Rapid mass-transfer provides high column efficiency and, using short columns, chiral resolution can be achieved in less than 20 sec. The application area is described which also involves the separation of α-hydroxy carboxylic acids.