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High-performance liquid chromatography filler with switchable chiral selectivity and preparing method thereof

A high-performance liquid chromatography, chiral technology, applied in the field of high-performance liquid chromatography packing and its preparation, to achieve the effects of good physical and chemical properties, high mechanical strength and lower detection limit

Inactive Publication Date: 2016-05-11
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing commercial columns cannot ensure that the enantiomer with a small content is eluted first, so the elut

Method used

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  • High-performance liquid chromatography filler with switchable chiral selectivity and preparing method thereof
  • High-performance liquid chromatography filler with switchable chiral selectivity and preparing method thereof
  • High-performance liquid chromatography filler with switchable chiral selectivity and preparing method thereof

Examples

Experimental program
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Example Embodiment

[0032] Example 1

[0033] Preparation of chiral stationary phase based on L-arabinose:

[0034] (1) Weigh 2g of silicon balls, react with 1mol / L HCl at 90°C for 3h, filter, wash with purified water to neutrality, and then dry at 150°C overnight for later use;

[0035] (2) Weigh 1.2 g of activated silicon balls, use toluene as a solvent, add 0.54 mL (3 mmol) of 3-aminopropyltrimethoxysilane (APTES), and react at room temperature for 16 hours. Centrifuge the toluene for 3 times and use toluene again. Suspend, add 0.24mL (3mmol) of pyridine, pipette 0.37mL (3mmol) of bromoisobutyryl bromide and dilute with 5mL of toluene, add dropwise to the reaction flask under nitrogen protection, react at 0°C for 2h, and react at room temperature overnight , Wash with toluene, water, methanol, dichloromethane, and acetone in sequence, and then vacuum dry at 110℃ for 3h;

[0036] (3) Using water, methanol and N,N-dimethylformamide in a volume ratio of 1:1:2 as a mixed solvent, the monomer N-isopropyla...

Example Embodiment

[0047] Example 2

[0048] Preparation of chiral stationary phase based on L-arabinose:

[0049] (1) Weigh 2g of silicon balls, react with 3mol / L HCl at 50-60℃ for 10h, filter, wash with purified water to neutrality, and then dry at 150℃ overnight for later use;

[0050] (2) Weigh 1.2 g of activated silicon balls, use toluene as a solvent, add 0.54 mL (3 mmol) of 3-aminopropyltriethoxysilane, and react at room temperature for 16 hours. Centrifuge the toluene three times and suspend again with toluene. Add 0.24mL (3mmol) of pyridine, pipette 0.37mL (3mmol) of bromoisobutyryl bromide and dilute with 5mL of toluene, add dropwise to the reaction flask under nitrogen protection, react at 0℃ for 2h, and react at room temperature overnight. Wash with toluene, water, methanol, dichloromethane and acetone in sequence, and then vacuum dry for 3h at 110℃;

[0051] (3) Mix water, methanol and N,N-dimethylformamide at a volume ratio of 1:1:2 as a mixed solvent, and add the monomer pure phenylboron...

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Abstract

The invention discloses high performance liquid chromatography filler with invertible chiral enantiomer selectivity. Functional monomers containing benzeneboronic acid are copolymerized to the surface of a silicon ball, and based on the invertible and switchable peculiar property of boron ester dynamic covalent bonds, D-type or L-type chiral molecules can be hinged to the surface of a stationary phase material in an invertible mode. When a D-type carbohydrate is bonded with a stationary phase in a covalent mode under the alkaline condition, at the moment, the stationary phase has a chiral separation function based on D-type carbohydrate; when D-type carbohydrate is eluted under the acidic condition, then L-type carbohydrate is bonded with the stationary phase in a covalent mode under the alkaline condition, and at the moment, the stationary phase has a chiral separation function based on L-type carbohydrate. When the prepared filler is used for separating and preparing chiral enantiomer, a small quantity of chiral substances can appear at first, which is beneficial for lowering detection limitation and improving accuracy, and the filler plays an important role in chiral medicine separation and preparation.

Description

technical field [0001] The invention belongs to the technical field of high-performance liquid chromatography packing materials, and more specifically relates to a chiral switchable high-performance liquid chromatography packing and its preparation method and application. Background technique [0002] As an important method for the separation and analysis of enantiomers, chiral liquid chromatography columns are widely used in the fields of biology, chemistry and medicine. Commonly used commercial chiral liquid chromatography stationary phases include covalently bonded amylose derivatives, cellulose derivatives, and crown ether derivatives on the surface of silica gel. In the pharmaceutical industry, an enantiomer drug with the opposite configuration often has side effects or even toxicity, and the chiral enantiomer with a very small content is eluted first, which plays an important role in the separation and analysis of enantiomers (can reduce detection limit and improve pr...

Claims

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Application Information

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IPC IPC(8): B01J20/292B01J20/285B01J20/30
CPCB01J20/285B01J20/292B01J2220/54
Inventor 魏为力王路军夏之宁张欢
Owner CHONGQING UNIV
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