Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography
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.
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Full corrected version of the protocol Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography
Table 2 Microanalysis results
Table 1 Troubleshooting table
This protocol has been modified since its initial publication. On the 8th of June 2012, the title and author list were changed as follows:Previously: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromagraphy Weihua Tang, Siu-Choon Ng & Ren-Qi WangCorrected: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography Ren-Qi Wang, Teng-Teng Ong, Ke Huang, Weihua Tang & Siu-Choon NgA few minor changes were made in the main text. The full version of the protocol with the changes marked in red can be found here
This protocol has been modified since its initial publication. On the 8th of June 2012, the title and author list were changed as follows:Previously: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromagraphy Weihua Tang, Siu-Choon Ng & Ren-Qi WangCorrected: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography Ren-Qi Wang, Teng-Teng Ong, Ke Huang, Weihua Tang & Siu-Choon NgA few minor changes were made in the main text. The full version of the protocol with the changes marked in red can be found here
Posted 06 Jun, 2012
Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography
Posted 06 Jun, 2012
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.
Figure 1
Figure 2
Figure 3
This protocol has been modified since its initial publication. On the 8th of June 2012, the title and author list were changed as follows:Previously: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromagraphy Weihua Tang, Siu-Choon Ng & Ren-Qi WangCorrected: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography Ren-Qi Wang, Teng-Teng Ong, Ke Huang, Weihua Tang & Siu-Choon NgA few minor changes were made in the main text. The full version of the protocol with the changes marked in red can be found here
This protocol has been modified since its initial publication. On the 8th of June 2012, the title and author list were changed as follows:Previously: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromagraphy Weihua Tang, Siu-Choon Ng & Ren-Qi WangCorrected: Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography Ren-Qi Wang, Teng-Teng Ong, Ke Huang, Weihua Tang & Siu-Choon NgA few minor changes were made in the main text. The full version of the protocol with the changes marked in red can be found here
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