Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Liquid Chromatographic Resolution of N-(3,5-Dinitrobenzoyl)-α-amino Acids on a New Chiral Stationary Phase: the First Liquid Chromatographic Utilization of a Double-Ureide Pocket for the Recognition of Chiral Carboxylate Anions

  • Hyun, Myung-Ho (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Kim, Seung-Nam (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Choi, Hee-Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Sakthivel, Pachgounder (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
  • Published : 2007.11.20
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Abstract

An HPLC chiral stationary phase (CSP) which has only two ureide functional groups was prepared starting from (1S,2S)-1,2-diaminocyclohexane. The CSP was successful in the resolution of various N-(3,5- dinitrobenzoyl)-α-amino acids, the separation (α) and the resolution factors (RS) being within the range of 1.11-1.35 and 2.19-5.17, respectively with the use of 20% 2-propanol in hexane containing 0.1% trifluoroacetic acid as a mobile phase. However, ethyl esters of N-(3,5-dinitrobenzoyl)-α-amino acids were not resolved or resolved with only marginal separation and resolution factors on the CSP under the identical mobile phase condition. From these results, the complexation of the carboxylate anions of analytes inside the double-ureide pocket of the CSP was expected to play some important role for the chiral recognition. In contrast, N-(3,5- dinitrobenzoyl)-α-amino acid N-propylamides were resolved on the CSP with reasonable separation and resolution factors. Enantioselective hydrogen bonding interactions between analytes and the CSP were presumed to be responsible for these resolutions.

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