This is a protocol preprint, a preliminary version of a manuscript that has not completed peer review at a journal. Research Square does not conduct peer review prior to posting preprints. The posting of a preprint on this server should not be interpreted as an endorsement of its validity or suitability for dissemination as established information or for guiding clinical practice.
Method Article
Ren-Qi Wang
Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 16 Nanyang Drive, Singapore 637722, Singapore
Corresponding Author
Siu-Choon Ng
Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 16 Nanyang Drive, Singapore 637722, Singapore
Corresponding Author
License:
This work is licensed under a CC BY-NC 3.0 License. Read Full License
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.
Keywords
chiral separation, chiral stationary phases, cyclodextrin, radical copolymerization
Figure 1
Figure 2
Figure 3
The authors declare that they have no competing financial interests.
This is a list of supplementary files associated with this preprint. Click to download.
- supplement0.doc
Full corrected version of the protocol Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography
- supplement0.pdf
Table 2 Microanalysis results
- supplement0.pdf
Table 1 Troubleshooting table
Loading...
Version History
CURRENT STATUS: Posted
Version 1
Posted 06 Jun, 2012
Community comments: 2
Metrics
Comments: 0
HTML Views: ...
Associated Publications
Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography
by Ren-Qi Wang, Teng-Teng Ong, Weihua Tang, +1
Analytica Chimica Acta (05 June, 2012)
Chemically bonded cationic β-cyclodextrin derivatives as chiral stationary phases for enantioseparation applications
by Ren-Qi Wang, Teng-Teng Ong, and Siu-Choon Ng
Tetrahedron Letters (05 June, 2012)
Chemically bonded cationic β-cyclodextrin derivatives and their applications in supercritical fluid chromatography
by Ren-Qi Wang, Teng-Teng Ong, and Siu-Choon Ng
Journal Of Chromatography A (05 June, 2012)
Method Article
Ren-Qi Wang
Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 16 Nanyang Drive, Singapore 637722, Singapore
Corresponding Author
Siu-Choon Ng
Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 16 Nanyang Drive, Singapore 637722, Singapore
Corresponding Author
Version History
CURRENT STATUS: Posted
Version 1
Posted 06 Jun, 2012
Community comments: 2
Metrics
Comments: 0
HTML Views: ...
License:
This work is licensed under a CC BY-NC 3.0 License. Read Full License
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
Loading...
Associated Publications
Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography
by Ren-Qi Wang, Teng-Teng Ong, Weihua Tang, +1
Analytica Chimica Acta (05 June, 2012)
Chemically bonded cationic β-cyclodextrin derivatives as chiral stationary phases for enantioseparation applications
by Ren-Qi Wang, Teng-Teng Ong, and Siu-Choon Ng
Tetrahedron Letters (05 June, 2012)
Chemically bonded cationic β-cyclodextrin derivatives and their applications in supercritical fluid chromatography
by Ren-Qi Wang, Teng-Teng Ong, and Siu-Choon Ng
Journal Of Chromatography A (05 June, 2012)