Authors
Ren-Qi Wang, Teng-Teng Ong, Ke Huang, Weihua Tang, Siu-Choon Ng
Summary
We described a facile and effective protocol wherein radical copolymerization is employed to covalently bond cationic β-cyclodextrin (β-CD) onto silica particles with extended linkage, resulting in a chiral stationary phase (IMPCSP) that can be used for the enantioseparation of racemic drugs in both high-performance liquid chromatography (HPLC) and supercritical fluid chromatography (SFC). Starting from commercially available chemicals, the IMPCSP is prepared in several steps: (i) reaction of β-CD with 1-(p-toluenesulfonyl)-imidazole to afford mono-6A-(p-toluenesulfonyl)-6A-deoxy-β-cyclodextrin (B); (ii) nucleophilic addition between B and 1-vinylimidazole and followed by treatment with anionic-exchange resin to give mono-vinylimidazolium-CD chloride (C); (iii) electrophilic addition between C and phenyl isocyanate to generate 6A-(3-vinylimidazolium)-6-deoxyperphenylcarbamate-β-CD chloride (D); (iv) reaction of silica gel with 3-methacryloxypropyltrimethoxysilane to engender vinylized silica (E); (v) immobilization of C onto vinylized silica via radical copolymerization with 2,3-dimethyl-1,3-butadiene in the presence of 2,2’-azobis(2-methylpropionitrile) (AIBN) to afford the desired chiral stationary phases. The overall IMPCSP preparation and column packing protocol requires ~2 weeks.
Further details
The protocol was published on Protocol Exchange on 6 June 2012. To see the entire protocol, click on the source link.
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