Zwitterionic codeine-derived methacrylate monoliths for enantioselective capillary electrochromatography of chiral acids and chiral bases

Electrophoresis
Enrique Javier Carrasco-CorreaM Lämmerhofer

Abstract

Thiol-ene click reaction of N-acetyl-L-cysteine methyl ester to codeine, followed by reaction with allyl isocyanate and hydrolysis to the corresponding zwitterionic chiral selector and its subsequent bonding to the surface of a methacrylate monolith provided a new chiral capillary column for enantiomer separation of chiral acids and chiral bases. First, the epoxy groups of a poly(glycidyl methacrylate-co-ethylene dimethacrylate) monolith were converted into amine residues, followed by reaction with allylglycidyl ether. In this way, a spacer arm was bonded to the surface before coating and cross-linking poly(3-mercaptopropyl methylsiloxane) (PMPMS) via radical addition (thiol-ene click reaction) to the surface. In order to improve the performance of the monolithic chiral stationary phase, thio ether and residual thiol groups were oxidized to sulfonyl and sulphonate groups, respectively. This novel chiral stationary phase (CSP) was evaluated by capillary electrochromatography (CEC) using two chiral model compounds, namely N-3,5-dinitrobenzoyl-R,S-leucine (retained by anion-exchange mechanism) and mefloquine (by cation-exchange process). The ion-exchange retention mechanism on the CSP was characterized for these two counterionic m...Continue Reading

References

Feb 24, 2001·Journal of Chromatography. a·N M MaierW Lindner
Dec 20, 2005·Psychiatry Research·Thomas D Meyer, Silke Maier
May 23, 2006·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Karel StulíkPavel Coufal
Jul 13, 2006·Journal of Separation Science·Giovanna CancelliereClaudio Villani
Sep 2, 2008·Journal of Chromatography. a·Vida FrankovicAles Strancar
Feb 20, 2010·Journal of Separation Science·Bezhan Chankvetadze
Jun 14, 2013·Journal of Chromatography. a·Enrique Javier Carrasco-CorreaJosé Manuel Herrero-Martínez
May 20, 2014·Journal of Chromatography. a·Ross M WoodsDaniel W Armstrong
May 4, 1998·Angewandte Chemie·Yoshio Okamoto, Eiji Yashima

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Citations

Jan 8, 2020·Journal of Separation Science·Lin-Feng HuFeng-Qing Yang
May 2, 2020·Journal of Chromatography. a·Christian GeibelMichael Lämmerhofer

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