PMID: 11925202Apr 2, 2002Paper

Effect of multivalency on the performance of enantioselective separation media for chiral HPLC prepared by linking multiple selectors to a porous polymer support via aliphatic dendrons

The Journal of Organic Chemistry
Frank H LingJean M J Fréchet

Abstract

Chiral stationary phases (CSPs) containing L-proline indananilide chiral selectors attached through a multivalent dendritic linker to monodisperse macroporous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate) beads have been prepared using two different approaches. The convergent method involves the preparation of ligands in solution and their subsequent attachment to the support. The divergent approach is based on the stepwise "on-bead" formation of the linker using methods that are typical of solid-phase synthesis. While the convergent CSPs feature well-defined ligands, their loading is relatively low. In contrast, the divergent technique affords CSPs with higher loading but with more limited control over precise ligand architecture. Excellent enantioselectivities characterized by separation factors of up to 31 were achieved for the separation of racemic N-(3,5-dinitrobenzoyl)-alpha-amino acid alkyl amides with these new CSPs under normal-phase HPLC conditions.

References

Jan 5, 1996·Journal of Chromatography. a·J Caldwell
Apr 16, 1999·Analytical Chemistry·P MurerJ M Fréchet
Sep 28, 1999·Pharmaceutical Science & Technology Today·M Liu, J M Fréchet
Sep 14, 2000·Journal of Colloid and Interface Science·A I Liapis, B A Grimes
Feb 24, 2001·Journal of Chromatography. a·C W HenryI M Warner

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Citations

Dec 4, 2008·Journal of Separation Science·Michael D SlaterFrantisek Svec
Mar 4, 2009·Analytical and Bioanalytical Chemistry·Gerard P O'SullivanKlaus Albert
Nov 10, 2005·Journal of Separation Science·Milan J BenesFrantisek Svec

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