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The effect of structure on the resolution of dansyl amino acids using beta-cyclodextrin as a mobile phase additive in reversed-phase thin-layer chromatography

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Summary

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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  1. Chemistry Department, State University of New York at Oswego, 13126, Oswego, NY, USA

    J. W. LeFevre, E. D. Rogers, L. L. Pico & C. L. Botting

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  1. J. W. LeFevre
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  2. E. D. Rogers
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  3. L. L. Pico
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  4. C. L. Botting
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LeFevre, J.W., Rogers, E.D., Pico, L.L. et al. The effect of structure on the resolution of dansyl amino acids using beta-cyclodextrin as a mobile phase additive in reversed-phase thin-layer chromatography. Chromatographia 52, 648–652 (2000). https://doi.org/10.1007/BF02789765

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  • DOI: https://doi.org/10.1007/BF02789765

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