The Design of Chiral Separation Media Using Monodisperse Functionalized Macroporous Beads: Effects of Polymer Matrix, Tether, and Linkage Chemistry

Kevin Lewandowski, Peter Murer, Frantisek Svec, Jean Frechet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

71 Scopus citations

Abstract

Porous size monodisperse methacrylate beads containing amino and hydroxyl groups, which can be used as a platform for the production of chiral separation media, have been prepared using the staged templated suspension polymerization process. The monomers 2-hydroxyethyl methacrylate and several tert-butoxycarbonyl-protected aminoalkyl methacrylates were used for the preparation of both hydroxyl- and amino-functionalized beads. Attachment of a chiral selector based on L-valine-3,5-dimethylanilide through a carbamate and a urea linkage, respectively, provides chiral stationary phases with excellent enantioselectivities in the separation of the enantiomers of 3,5-dinitrobenzamido derivatives of α-amino acids. For comparison purposes, a separation medium was also prepared by the direct polymerization of a chiral monomer analogous to the hydroxyethyl methacrylate-based stationary phase. The chiral stationary phases prepared with the N-methyl-2-aminoethyl methacrylate platform exhibit the best selectivity, and separation factors as high as 15 were achieved under normal-phase HPLC conditions.

Original languageEnglish (US)
Pages (from-to)1629-1638
Number of pages10
JournalAnalytical Chemistry
Volume70
Issue number8
DOIs
StatePublished - Apr 15 1998

ASJC Scopus subject areas

  • Analytical Chemistry

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