Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Liquid Chromatographic Resolution of Vigabatrin and Its Analogue γ-Amino Acids on Chiral Stationary Phases Based on (3,3'-Diphenyl-1,1'-binaphthyl)-20-crown-6

  • Choi, Hee-Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Cho, Hwan-Sun (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Lee, Su-Jin (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Hyun, Myung-Ho (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
  • Received : 2011.02.23
  • Accepted : 2011.05.03
  • Published : 2011.08.20
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Abstract

Two chiral stationary phases (CSPs) based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 bonded covalently to silica gel were applied for the first time to the resolution of racemic vigabatrin and its analogue ${\gamma}$-amino acids and the resolution results were compared to those on the commercially available Crownpak CR(+) based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 coated dynamically onto octadecylsilica gel. While vigabatrin was not resolved at all on Crownpak CR(+), it was resolved quite well on the two CSPs. Among four vigabatrin analogue ${\gamma}$-amino acids, only two were resolved on Crownpak CR(+), but three were resolved on the CSP (CSP 1) containing residual silanol groups and all of four were resolved on the CSP (CSP 2) containing residual silanol group-protecting n-octyl groups. The improved lipophilicity in CSP 2 was proposed to be responsible for its superiority to CSP 1 for the resolution of vigabatrin and analogue ${\gamma}$-amino acids. In addition, the composition of aqueous mobile phase was found to affect the chiral recognition behaviors for the resolution of vigabatrin and analogue ${\gamma}$-amino acids on CSP 2.

Keywords

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