Enantioseparation of protonated primary arylalkylamines and amino acids containing an aromatic moiety on a pyridino-crown ether based new chiral stationary phase |
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| Institution: | 1. Institute of Chemistry, Eötvös Loránd University, H-1518 Budapest, 112. PO Box 32, Hungary;2. Institute for Organic Chemistry, Budapest University of Technology and Economics, H-1521 Budapest, PO Box, 91, Hungary;3. Reanal Fine Chemicals Co., H-1147 Budapest, Telepes u. 53, Hungary;1. Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, 84.W. South Street, Wilkes-Barre, PA 18766, USA;2. Department of Molecular Genetics, University of Lodz, Lodz 90-236, Poland;3. Department of Cytobiochemistry, University of Lodz, 90-236 Lodz, Poland;1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic;2. Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovsky sq. 2, 162 06 Prague, Czech Republic;1. Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland;2. Institute of Chemistry and Environmental Protection and Biotechnology, Jan Dlugosz University, Armii Krajowej 13/15, 42-200 Czestochowa, Poland;1. Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, 84 W. South Street, Wilkes-Barre, PA 18766, USA;2. Department of Molecular Genetics, University of Lodz, Lodz 90-236, Poland;3. Department of Organic Chemistry, University of Lodz, Lodz 91-403, Poland |
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| Abstract: | This paper reports the preparation and testing of a new pyridino-18-crown-6 ether based chiral stationary phase (CSP). The chiral crown ether was covalently bound to silica gel. Circular dichroism (CD) spectroscopy was used for probing the complex formation of the chiral crown ether with the enantiomers of protonated primary arylalkylamines. The (S,S)-dimethylpyridino-18-crown-6 ether selector having a terminal double bond was first transformed to a triethoxysilyl derivative by regioselective hydrosilylation, and then heated with spherical HPLC quality silica gel to obtain the CSP. The discriminating power of the HPLC column filled with the above CSP was tested by using the hydrogenperchlorate salts of racemic α-(1-naphthyl)ethylamine (1-NEA), α-(2-naphthyl)ethylamine (2-NEA) and the hydrochloride salts of aromatic α-amino acids and α-amino acids containing different aromatic side-chain protecting groups. |
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