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Chromatographic Resolution of alpha-Amino Acids by (R)-(3,3′-Halogen Substituted-1,1′-binaphthyl)-20-crown-6 Stationary Phase in HPLC
Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3′-halogen substituted-1,1′-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one alpha-amino acids have different degrees of separation on R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1′-binaphthyl)-20-crown-6 derivatives. Both the separation factors (alpha) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6 chiral stationary phase.
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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI