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Synthesis of a Novel β-cyclodetrin Chiral Stationary Phase and Its Application in HPLC

Author: ZhangShaoPeng
Tutor: TangWeiHua
School: Nanjing University of Technology and Engineering
Course: Chemical Engineering
Keywords: Chiral stationary phase cyclodextrin chiral separation Click chemistry High performance liquid chromatography
CLC: O657.72
Type: Master's thesis
Year: 2014
Downloads: 29
Quote: 0
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Abstract


With the development of society and technology, people come to realize the relation between the chiral phenomenon and our life. Increasing need of monoenantiotropic drug and more concern of the pharmacodynamics and the side-effect make it more important in the chiral separation. High performance liquid chromatography (HPLC) has much advantage such as high performance, high sensitivity, fast analysis and widely using, which make HPLC to be an important technique in the field of chiral separation. Click chemistry is a mild and steady way in chemistry reactions, so it is commonly used for obtained chiral stationary phase (CSP) now.In this thesis, a novel β-cyclodextrin-based chiral stationary phase (CSP) has been prepared by immobilization of3-chloro-4-methylperphenylcarbamated mono-6-azido-β-CD to alkynylated silica via "click chemistry". All the products have been prepared with facile synthetic routes and structure fully confirmed with1HNMR, FT-IR or Elemental analysis (EA). Besides, chiral separation of aryl alcohols, flavanoids and P-blockers in HPLC showed good resolutions. The thesis contains three parts:(1).The synthesis of CSP. We designed a mild and steady reaction way to obtain Ts-Im, Ts-CD, N3-CD, derivatized cyclodextrin, alkynyl silica, and CCC-CSP respectively.(2).The study of separation ability of per-3-chloro-4-methylphenylcarbamated β-cyclodextrin CSP (CCC-CSP). Firstly, the CCC-CSP was packed as a HPLC column and tested by the influence of flowrate and different mobile phase. And then the enantio-separation ability of CCC-CSP was studied with aryl alcohols, flavanoids and P-blockers under reverse phase. Finally, the results showed that the bringing of3-position chloro and4-position methyl can enhance the dipole-dipole interaction of amides group and the hydrogen bonding, so the CCC-CSP has a better enantioseparation ability for aryl alcohols and flavanoids.(3).The study of separation ability of CD-CSP. The chiral separation ability of β-cyclodextrin clicked CSP (CD-CSP) was tested by aryl alcohols, flavanoids and pharmaceutical drugs and searched for the best separation condition for every racemic. Then we studied the separation principle of CD-CSP. Finally, with the comparing of different resolution between CD-CSP and CCC-CSP, we can study the influence of the different CD immobilized to silica.In summary, this thesis successfully prepared a novel CCC-CSP which shows good enantioseparation ability for many chiral drugs. This research offers a support for enantioseparation of racemics and a plateform for designing novel CD CSPs.

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CLC: > Mathematical sciences and chemical > Chemistry > Analytical Chemistry > Instrument analysis ( physics and physical chemistry ) > Chromatographic analysis > Liquid chromatography analysis
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