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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 10
BKCSDE 34(10)
October 20, 2013 

Resolution of Tocainide and Its Analogues on a Doubly Tethered N-CH3 Amide Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid
Kyu Jung Lee, Kyung Mi Tak, Myung Ho Hyun*
Chiral stationary phase, Enantioselective separation, Liquid chromatography, Tocainide
A doubly tethered N-CH3 amide chiral stationary phase (CSP 4) based on (+)-(18-crown-6)-2,3,11,12- tetracarboxylic acid was applied to the resolution of an antiarrythmic agent, tocainide, and its analogues and the chromatographic resolution results were compared with those on a singly tethered N-H amide CSP (CSP 1), a singly tethered N-CH3 amide CSP (CSP 2) and a doubly tethered N-H amide CSP (CSP 3) under an identical aqueous mobile phase condition. CSP 4 was found to be generally better than other CSPs in terms of the separation factors (α) and resolutions (RS). The retention times of analytes denoted by the retention factors (k1) on CSP 4 were quite long compared to those on other CSPs because of the improved lipophilicity of CSP 4. The long retention times of analytes on CSP 4 were successfully controlled by the addition of a small amount of ammonium acetate to aqueous mobile phase without hurting the chiral recognition efficiency. The variation of the content and type of organic and acidic modifier in aqueous mobile phase was found not to change the chiral recognition efficiency significantly.
2978 - 2982
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