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Preparation method of immobilized beta-cyclodextrin derivative type chiral stationary phase

A chiral stationary phase and cyclodextrin technology, applied in the field of high performance liquid chromatography, can solve the problem of reducing the chiral separation ability of the bonded cyclodextrin chiral stationary phase, increasing the achiral recognition effect, and low spatial regularity. The problem is to achieve the effect of an effective preparation method, simple post-processing and purification, and fast reaction rate.

Inactive Publication Date: 2013-11-27
三亚哈尔滨工程大学南海创新发展基地
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Problems solved by technology

However, the bonded cyclodextrin chiral stationary phase usually has disadvantages such as many reaction steps and low bonding efficiency, so that the surface of the silica gel has few substances with chiral recognition ability and the spatial regularity is not high. In addition, the presence of spacer molecules increases. The achiral recognition effect is reduced, thereby reducing the chiral separation ability of the bonded cyclodextrin chiral stationary phase

Method used

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  • Preparation method of immobilized beta-cyclodextrin derivative type chiral stationary phase
  • Preparation method of immobilized beta-cyclodextrin derivative type chiral stationary phase
  • Preparation method of immobilized beta-cyclodextrin derivative type chiral stationary phase

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Experimental program
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Effect test

Embodiment 1

[0024]Add 0.9g of completely dried β-cyclodextrin into a reactor containing 15ml of anhydrous pyridine, raise the temperature to 80°C under a nitrogen atmosphere, and add 0.6ml of propyl triethoxyisocyanate when all the solids are dissolved base silane, kept at a constant temperature of 80°C, and stirred for 12 hours. Then add 1.2ml of phenylisocyanate, keep the temperature at 80°C, stir for 24h, and stop heating. [0013] The cooled pyridine solution containing the product is added dropwise in the vigorously stirred 300ml aqueous methanol solution (methanol / water=4 / 1, v / v), producing a large amount of white precipitates. After continuing to stir vigorously for 15 minutes, stop stirring, and after standing still for 15 minutes, pour out the supernatant. The suspension containing a large amount of solids in the lower part was centrifuged at high speed to separate the solid product. After centrifugation, add 30ml of methanol aqueous solution (methanol / water=4 / 1, v / v) to wash, an...

Embodiment 2

[0029] The reaction steps and conditions are the same as those in Example 1, the substrate used is 4-methylphenylisocyanate, and its consumption is 1.4ml. Finally, a 4-methylphenylcarbamate β-cyclodextrin chiral column was obtained.

Embodiment 3

[0031] The reaction steps and conditions are the same as in Example 1, the substrate used is 4-chlorophenylisocyanate, and its consumption is 1.70g. Finally, a 4-chlorophenylcarbamate β-cyclodextrin chiral column was obtained.

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Abstract

The invention provides a preparation method of an immobilized beta-cyclodextrin derivative type chiral stationary phase. The preparation method comprises the following steps: reacting isocyanate propyl triethoxy silane with beta-cyclodextrin; performing derivatization modification on a hydroxyl group on a beta-cyclodextrin glucose unit by using phenyl isocyanate to obtain a beta-cyclodextrin derivative; coating the beta-cyclodextrin derivative bonded with a small amount of silane coupling agent on the surface of aminopropyl silica gel, and performing condensation in ethanol / aqueous solution in the presence of trimethylchlorosilane by using the silane coupling agent in the beta-cyclodextrin derivative molecules to finally obtain the immobilized beta-cyclodextrin derivative type chiral stationary phase, wherein the phenylcarbamate beta-cyclodextrin derivative molecules are connected by using a silicon-oxygen-silicon bond to form an inclusion netlike structure which covers the surface of the aminopropyl silica gel. The preparation method has the characteristics of simplicity, few steps and high bonding efficiency, can be applied to the normal-phase high-performance liquid chromatographic condition, and has the advantages of high chromatographic column stability and high chiral separation capacity.

Description

technical field [0001] The present invention relates to a method for preparing a chiral stationary phase, specifically to immobilize β-cyclodextrin derivatives on aminopropyl silica gel by using a silane coupling agent condensation method for β-cyclodextrin derivatives On the surface, the immobilized β-cyclodextrin derivative chiral stationary phase is prepared, which is suitable for the field of high performance liquid chromatography. Background technique [0002] Chirality is a phenomenon ubiquitous in natural organisms. The physical and chemical properties of different optical isomers of chiral compounds are almost identical, but they often show differences when interacting with organisms, especially In the field of medicine, the differences in efficacy and toxicity between optical isomers are more significant. Therefore, it is necessary to investigate the enantiomers of chiral drugs separately to understand the physiological activities of different enantiomers in order ...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30
Inventor 陈兴娟杨光雷盛晋晋
Owner 三亚哈尔滨工程大学南海创新发展基地
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