Abstract
Reversed-phase thin-layer chromatographic separations of enantiomers of dansyl amino acids with varying structures were performed to determine the structural features necessary for enantioselection by beta-cyclodextrin (β-CD), a chiral mobile phase additive. In general, an increase in side chain length and increased branching caused a corresponding increase in the separation factor, alpha (α). The chiral center of the DNS-amino acid must be in close proximity to the (N,N-dimethylamino)naphthyl moiety for separation to occur. Eight DNS-DL-amino acid pairs were resolved for the first time using this methodology. New syntheses are reported forN-ɛ-DNS-D-lysine andO-DNS-D-tyrosine.
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