Abstract
A new high-performance liquid chromatography chiral stationary phase (CSP) was prepared by bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid to silica gel. The new CSP was employed in separating the two enantionmers of various natural and unnatural racemic α-amino acids and their derivatives. All natural and unnatural racemic α-amino acids tested were resolved with reasonable separation factors on the new CSP, except for proline, which does not contain a primary amino group. Racemic α-amino acid derivatives were also tested for their separability on the new CSP. In general, N-monoalkyl amides of α-amino acids were resolved better than the corresponding free α-amino acids. However, N, N-dialkyl amides and esters of α-amino acids were not resolved as well as the corresponding free α-amino acids, except for phenylglycine derivatives. In the case of phenylglycine, both N-monoalkyl and N, N-dialkyl amides of phenylglycine were resolved better than phenylglycine itself and its ester derivative.
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