Direct separation of the enantiomers of reboxetine by liquid chromatography on different cellulose- and amylose-based chiral stationary phases |
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Authors: | R Ficarra M L Calabrò S Tommasini S Melardi P Cutroneo P Ficarra |
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Institution: | 1. Department of Pharmaco-Biological Sciences, University of Catanzaro “Magna Gr?cia”, Complesso “Ninì Barbieri”, 88021, Roccelletta di Borgia, Catanzaro, Italy 2. Department of Medicinal Chemistry, University of Messina, Viale Annunziata, 98168, Messina, Italy
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Abstract: | Summary Racemic reboxetine, (R,S)-2(R,S)-α-(2-ethoxyphenoxybenzyl] morpholine methane sulfonate, is a mixture of the (R,R) and (S,S) enantiomers. Separation of the enantiomers of reboxetine by liquid chromatography has been investigated on three chiral
stationary phases—cellulose tris-(3,5-dimethylphenylcarbamate) (Chiralcel OD), cellulose tris-(phenylcarbamate) (Chiralcel
OC), and amylose tris-(3,5-dimethylphenylcarbamate) (Chiralpak AD). On these stationary phases the resolution of the (R,R) and (S,S) enantiomers was highly dependent on mobile-phase composition. When Chiralcel OD and OC were used, addition of diethylamine
to the mobile phase greatly improved the separation of the enantiomers. On Chiralpak AD enantio-separation was achieved without
the use of additives. Solute-mobile phase-stationary phase interactions which might participate in the mechanism of enantiorecognition
are discussed. |
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Keywords: | Column liquid chromatography Enantioselectivity Chiralcel OD and OC Chiralpak AD Reboxetine |
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