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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 8
BKCSDE 32(8)
August 20, 2011 

Liquid Chromatographic Resolution of Vigabatrin and Its Analogue g-Amino Acids on Chiral Stationary Phases Based on (3,3’-Diphenyl-1,1’-binaphthyl)-20-crown-6
Hee Jung Choi, Hwan Sun Cho, Su Jin Lee, Myung Ho Hyun *
Chiral stationary phase, Chiral crown ether, Enantiomeric resolution, Liquid chromatography, Vigabatrin, γ-Amino acids
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 γ-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 γ-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 γ-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 γ-amino acids on CSP 2.
3017 - 3021
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