This is a 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
Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography
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
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
commented on 07 June, 2012
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
commented on 07 June, 2012
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
Badges
Prescreen
This manuscript passed our Prescreen assessment
Complete author information
Appropriate declaration statements
Potential risks to human health
Prescreen
History
CURRENT STATUS: Posted
Version 1
Posted 06 Jun, 2012
Community comments: 2
Metrics
Comments: 2
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)
Learn more about our company.
This is a preprint. It has not completed peer review.
Method Article
Copolymerization preparation of cationic cyclodextrin chiral stationary phases for drug enantioseparation in chromatography
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
Badges
Prescreen
This manuscript passed our Prescreen assessment
Complete author information
Appropriate declaration statements
Potential risks to human health
Prescreen
History
CURRENT STATUS: Posted
Version 1
Posted 06 Jun, 2012
Community comments: 2
Metrics
Comments: 2
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
commented on 07 June, 2012
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
commented on 07 June, 2012
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
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)