In this study, perphenylcarbamated cyclodextrin clicked chiral stationary phase (CSP) was developed with high column efficiency. The characteristics of the column were evaluated in terms of linearity, limit of detection and limit of quantification. The enantioselectivity of the as-prepared clicked CSP was explored with 26 recemates including aryl alcohols, flavanoids and adrenergic drugs in reversed phase high-performance liquid chromatography. The effect of separation parameters including flow rate, column temperature, organic modifier and buffer on the enantioselectivity of the clicked CSP was investigated in detail. The correlation study of the analytes structure and their chiral resolution revealed the great influence of analytes' structure on the enantioseparations with cyclodextrin CSP. Methanol with 1% of triethylammonium acetate buffer (pH 4) was proved to be the best choice for the chiral separation of basic enantiomers.
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Evaluation of perphenylcarbamated cyclodextrin clicked chiral stationary phase for enantioseparations in reversed phase high performance liquid chromatography.
J Chromatogr A
October 2014
Key Laboratory of Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China. Electronic address:
In this study, perphenylcarbamated cyclodextrin clicked chiral stationary phase (CSP) was developed with high column efficiency. The characteristics of the column were evaluated in terms of linearity, limit of detection and limit of quantification. The enantioselectivity of the as-prepared clicked CSP was explored with 26 recemates including aryl alcohols, flavanoids and adrenergic drugs in reversed phase high-performance liquid chromatography.
View Article and Find Full Text PDFSynthesis of novel perphenylcarbamated β-cyclodextrin based chiral stationary phases via thiol-ene click chemistry.
Electrophoresis
October 2014
CAS Key Laboratory of Separation Science for Analytical Chemistry, National Chromatographic R&A Center, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Dalian, P. R. China; University of Chinese Academy of Sciences, Beijing, P. R. China; State Key Laboratory of Fine Chemicals and Department of Analytical Chemistry, Dalian University of Technology, Dalian, P. R. China.
Novel cyclodextrin (CD) chiral stationary phases (CD-CSPs) with well-defined structure have been successfully synthesized by immobilization of mono/di(10-undecenoyl)-perphenylaminocarbonyl β-CD on the 3-mercaptopropyl functionalized silica gel via thiol-ene click chemistry. The phenyl carbamate groups on the rims of CD extended the cavity of CD-CSPs, which facilitated the formation of inclusion complex with various types of racemic compounds under RP mode, and also improved the π-π stacking interaction, dipole-dipole interaction, and hydrogen bonding interaction with racemic compounds under normal phase mode. Fifteen racemic compounds were successfully separated on this CD-CSP with HPLC, and the chromatographic results also demonstrated that thiol-ene click chemistry affords a facile approach for preparation of CSPs.
View Article and Find Full Text PDF"Click" immobilized perphenylcarbamated and permethylated cyclodextrin stationary phases for chiral high-performance liquid chromatography application.
J Chromatogr A
July 2010
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore.
Two cyclodextrin-based chiral stationary phases have been prepared by immobilization of functionalized mono-6-azido-beta-CD derivatives to alkynyl modified silica via "click" chemistry and applied to the HPLC enantioseparation of various chiral compounds. The perphenylcarbamated CD CSP (CCP-CSP) exhibited excellent chiral recognition of a wide range of analytes including racemic aryl alcohols, flavonoids, bendroflumethiazide, atropine and some beta-blockers. Methanol proved to be a better organic modifier than acetonitrile for most of the analytes with the exception of bendroflumethiazide.
View Article and Find Full Text PDFApplication of Click-chemistry-based perphenylcarbamated beta-CD chiral stationary phase in CEC.
Electrophoresis
February 2009
School of Chemical & Biomedical Engineering, Nanyang Technological University, Singapore, Singapore.
A novel chiral stationary phase (CSP) was prepared by anchoring mono-6-azido-6-deoxyperphenylcarbamated beta-CD onto omega-alkynyl functionalized silica (5 microm) via organic soluble Cu(I)-catalyzed Click chemistry. The obtained CSP was thereafter packed into fused-silica capillary (100 microm id) with an effective length of 9 cm and tested in aqueous CEC to separate a series of racemic aryl alcohols. High separation factors with good resolution were achieved using the current novel CSP.
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