Summary
Chiral stationary phases (CSPs) were synthesized by reaction of aminopropylsilica (APS) with chiral monochloro-s-triazines (MCTs). MCTs were obtained by reaction of 2,4,6-trichloro-s-triazine (cyanuric chloride) with one equivalent of methanol and, subsequently, with one equivalent of L-prolinetert butyl ester (H-Pro-OtBu) orN-tert butyloxycarbonyl-L-lysinetert butyl ester (Boc-Lys-OtBu). End-capping of unreacted amino groups of APS with acetic anhydride, followed by trifluoroacetolytic cleavage of the protecting groups of amino acids (AAs), afforded two chiral stationary phases bearing either L-proline (CSP-3) or L-lysine (CSP-4) as chiral selector. Using ligand-exchange chromatography matography with addition of Cu2+ to the mobile phase, enantiomers of free DL-AAs and a fewN-(2,4-dinitrophenyl)-DL-AAs were separated on CSP-3, whereasN-(dansyl)-DL-AAs were separated on CSP-4.
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Dedicated to Professor Günther Jung, University of Tübingen, on the occasion of his 60th birthday
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Wachsmann, M., Brückner, H. Ligand-exchange chromatographic separation of DL-amino acids on aminopropylsilica-bonded chirals-triazines. Chromatographia 47, 637–642 (1998). https://doi.org/10.1007/BF02467446
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DOI: https://doi.org/10.1007/BF02467446