Abstract
A convenient liquid chromatographic method for the separation of α-amino acid esters as benzophenone Schiff base derivatives on coated chiral stationary phases (CSPs) (Chiralcel OD-H, Chiralcel OD, Chiralpak AD-H, Chiralpak AD, and Chiralpak AS) or covalently immobilized CSPs (Chiralpak IA, Chiralpak IB, and Chiralpak IC) derived from polysaccharide derivatives is described. Benzophenone imine derivatives of α-amino acid esters were readily prepared by stirring benzophenone imine and the hydrochloride salts of α-amino acid esters in 2-propanol. The chromatographic separations were conducted at a flow rate 1.0 mL/min and a detection wavelength of 254 nm; 0.5% 2-propanol/hexane (v/v) was used on CSPs. In general, the resolution of Chiralpak IC was superior to those of the other CSPs. In addition, the resolutions of other arylimine derivatives of α-amino acid esters and the effects of different mobile phases on the enantiomeric separation of α-amino acid esters as benzophenone imine derivatives on Chiralpak IC were investigated.
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References
Duchateau, A. L. L., Guns, J. J., Kubben, R. G. R., and van Tilburg, A. F. P., High-performance liquid chromatography of diamine enantiomers as Schiff bases on a chiral stationary phase. J. Chromatogr. A, 664, 169–176 (1994).
Francotte, E., Isolation and production of optically pure drugs by enantioselective chromatography, In Francotte, E. and Lindner, W. (Eds.), Chirality in Drug Research. Wiley-VCH, Weinheim, pp. 155–187, (2006).
Greene, T. W. and Wuts, P. G. M., Protective Groups in Organic Synthesis, 3rd Ed. John Wiley & Sons. Inc., New York, (1999).
Huang, H., Jin, J. Y., Hong, J. H., Lee, W., Han, H. K., and Kang, J. S., Liquid chromatopraphic enantiomer separation of amino acid esters as 9-anthraldimine Schiff bases using polysaccharide-derived chiral stationary phases. J. Liq. Chromatogr. Relat. Technol., 34, 209–216 (2011).
Jin, J. Y., Bae, S. K., and Lee, W., Comparative studies between covalently immobilized and coated chiral stationary phases based on polysaccharide derivatives for enantiomer separation of N-protected α-amino acids and their ester derivatives. Chirality, 21, 871–877 (2009).
Jin, J. Y., Lee, W., Park, J. H., and Ryoo, J. J., Covalently bonded and coated chiral stationary phases derived from poltsaccharide derivatives for enantiomer separation on N-fluorenylmethoxycarbonyl α-amino acids with fluorescence detection. J. Liq. Chromatogr. Relat. Technol., 29, 1793–1801 (2006).
Jin, J. Y., Lee, W., Park, J. H., and Ryoo, J. J., Liquid chromatographic enantiomer separation of N-phthaloyl protected α-amino acids on coated and immobilized chiral stationary phases derived from polysaccharide derivatives. J. Liq. Chromatogr. Relat. Technol., 30, 1–9 (2007).
O’Donnell, M. J. and Polt, R. L., A mild and efficient route to Schiff base derivatives of amino acids. J. Org. Chem., 47, 2663–2666 (1982).
Subramanian, G. (Ed.). Chiral Separation Techniques: A Practical Approach; 2nd Ed. VCH, Weinheim, (2001).
Thunberg, L., Hashemi, J., and Andersson, S., Comparative study of coated and immobilized polysaccharide-based chiral stationary phases and their applicability in the resolution of enantiomers. J. Chromatogr. B, 875, 72–80 (2008).
Zhang, T., Nguyen, D., and Franco, P., Enantiomer resolution screening strategy using multiple immobilized polysaccha-ride-based chiral stationary phases. J. Chromatogr. A, 1191, 214–222 (2008).
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Huang, H., Xu, W.J., Jin, JY. et al. A convenient method for the enantiomeric separation of α-amino acid esters as benzophenone imine Schiff base derivatives. Arch. Pharm. Res. 35, 1015–1019 (2012). https://doi.org/10.1007/s12272-012-0609-6
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DOI: https://doi.org/10.1007/s12272-012-0609-6