Comparison of ( S)-N-(3,5-dinitrobenzoyl)tyrosine derivatives as chiral selectors for high-performance liquid chromatographic enantioseparations

The synthesis of a new chiral stationary phase (CSP), based on immobilized ( S)-N-(3,5-dinitrobenzoyl)tyrosine methyl-ester, is described and its chromatographic behaviour and enantioselectivity are compared with those of a well known dinitrobenzoyltyrosine-derived stationary phase. In addition, a n...

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Bibliographic Details
Published in:Journal of Chromatography A 1995-03, Vol.694 (1), p.135-150
Main Authors: Veigl, E., Böhs, B., Mandl, A., Krametter, D., Lindner, W.
Format: Article
Language:English
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Summary:The synthesis of a new chiral stationary phase (CSP), based on immobilized ( S)-N-(3,5-dinitrobenzoyl)tyrosine methyl-ester, is described and its chromatographic behaviour and enantioselectivity are compared with those of a well known dinitrobenzoyltyrosine-derived stationary phase. In addition, a new “end-capping” procedure for the CSP to reduce polar but non-stereoselective selectand-selector interactions was developed and evaluated by analyzing a broad range of chiral compounds [e.g., ibuprofen-1-naphthylamide, benzoic acid 1-phenylethylamide, 1-(1-naphthyl)ethylphenylurea, sulfoxides, propranolol oxazolidin-2-one].
ISSN:0021-9673
DOI:10.1016/0021-9673(94)00792-8