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New Pirkle-Type Chiral Stationary Phases with Limited Approach to Silica Surface

Liquid chromatographic resolution of enantiomers on chiral stationary phases (CSPs) has been known as one of the most convenient and accurate tool for evaluating of purity and preparative separation of enantiomers, recently even on industrial scale. Consequently, various CSPs for this purpose have been developed. Pirkle– type CSPs have been known to separate enantiomers by forming energetically different transient diastereomeric p-donor/p-acceptor complexes. For the effective formation of such complexes between the CSP and racemic analyte, Pirkle– type CSPs have been usually designed to contain p-acidic (acceptor) or/and p-basic (donor) aromatic rings. In study presented here we wish to report the process of developing a new chiral stationary phases derived from the selected amino acids. All CSPs contain a strong p-acidic N-3, 5-dinitrobenzoyl group (DNB), which is expected to interact with various aromatic derivatives, and aromatic p-basic or alkyl group which controlled the approach to silica surface. The chiral selector is covalently bound at silica surface with the spacer which is placed behind the chiral center, so that in stationary phase the chiral hole of selector is ideally open for analytes approach. With such structure the chiral selection of CSPs is remained but the achiral interaction with polar silica surface are substantially diminished.

chiral stationary phase; liquid chromatography

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