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A kind of preparation method of cyclodextrin chromatography stationary phase

A chromatographic stationary phase and cyclodextrin technology, applied in the field of cyclodextrin-modified silica gel stationary phases, can solve the problems of difficult removal, restricting stationary phase separation efficiency, etc., and achieve the effects of high selectivity, saving reaction time, and avoiding residues

Active Publication Date: 2020-11-24
ACCHROM TECH (DALIAN) TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the click reaction catalyzed by Cu(I) has high efficiency and nearly 100% yield, the introduction of Cu catalyst reagents causes a small amount of Cu to remain in the reaction system, and this negative effect is very obvious in bioorthogonal reactions, because Cu The existence of the presence of life has certain toxicity, and it is difficult to remove; at the same time, the residue on the surface of the chromatographic stationary phase will also restrict the separation efficiency of the stationary phase; therefore, it is urgent to develop fast, simple, high bonding efficiency, and no Cu(I) catalysis method for the synthesis of chromatographic stationary phases

Method used

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  • A kind of preparation method of cyclodextrin chromatography stationary phase
  • A kind of preparation method of cyclodextrin chromatography stationary phase
  • A kind of preparation method of cyclodextrin chromatography stationary phase

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Under nitrogen protection, take 1.13g of epoxypropyltrimethoxysilane reagent, dissolve it in 20mL of anhydrous tetrahydrofuran solution, stir it electromagnetically, add 431mg of ADIBO reagent containing amino groups at the end and phenyl groups on both sides, and adjust with triethylamine. pH value, stirred at room temperature, and detected by liquid chromatography to obtain the ADIBO-modified silane reagent. Under nitrogen protection, dissolve the dried silica gel (1.5g) in 30mL of anhydrous toluene, add the ADIBO silane reagent prepared above, and dropwise add pyridine (6mmol, 480μL), heat to reflux, react for 24h, stop the reaction, and cool Suction filtration, washing with anhydrous toluene, tetrahydrofuran, methanol, water, methanol successively, drying and solidification at 80°C for 6 hours, to obtain silica gel activated by ADIBO reagent, named as S-oxy-ADIBO material.

[0024] Weigh 1.0 g of the above dried S-oxy-ADIBO material, under nitrogen protection, disso...

Embodiment 2

[0026] The difference from Example 1 is that the alkoxysilane reagent is a triethoxyisocyanosilane reagent, which (2.47g, 10mmol) is dissolved in 20mL of anhydrous THF solution, stirred electromagnetically, and added with an amino group at the end , ADIBO reagent (4.22 g, 10 mmol) containing methoxyphenyl groups on both sides, stirred at room temperature, and detected by liquid chromatography to obtain ADIBO modified isocyanosilane reagent. Under nitrogen protection, dissolve the dried silica gel (2.5g) in 30mL of anhydrous toluene, add the ADIBO silane reagent prepared above, and dropwise add pyridine (6mmol, 480μL), heat to reflux, react for 24h, stop the reaction, and cool Suction filtration, followed by washing with anhydrous toluene, tetrahydrofuran, methanol, water, methanol, drying and solidification at 80°C for 6 hours, to obtain silica gel activated by ADIBO reagent, named S-isocyano-MeO-ADIBO material;

[0027]Weigh 1.5g of the above dried S-isocyano-ADIBO material, ...

Embodiment 3

[0029] The difference from Example 2 is that the alkoxysilane reagent is an aminopropyltrimethoxysilane reagent modified by glutaraldehyde, and the ADIBO reagent has an amino group at the end and a phenyl group substituted by a sulfonic acid group on both sides; the cyclodextrin reagent First carried out derivatization, the derivatization reagent is isocyanobenzene, and the specific implementation method is:

[0030] At room temperature, to the prepared DMF solution (30mL) of cyclodextrin azide (3.48g, 3mmol), slowly add isocyanobenzene reagent (12mL, 60mmol) dropwise, add pyridine (30mL) and stir for 12h, pump Filter, and recrystallize the obtained isocyanobenzene derivatized azidocyclodextrin CPCD with acetone;

[0031] Dissolve glutaraldehyde-modified aminopropyltrimethoxysilane reagent (2.0g, 5mmol) in 20mL of anhydrous THF solution, stir electromagnetically, add ADIBO with amino groups at the end and phenyl groups substituted with sulfonic acid groups on both sides. The ...

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Abstract

The invention relates to the technical field of preparation of silica gel chromatographic stationary phase materials, in particular to a method for preparing a cyclodextrin chromatographic stationary phase. The method is characterized in that by virtue of the characteristics of a Strain-promoted azide-alkyne cycloaddition (SPAAC) click reaction, the surface of silica gel is modified with an ADIBO (with the characteristics that one end contains an octatomic ring alkynyl functional group and the other end contains amino, carboxyl, formyl and other nucleophilic functional groups easy for an addition reaction) agent with ring expanding tension, and then octatomic ring alkynyl and azide cyclodextrin or azide cyclodextrin derivatives are subjected to copper-less catalytic SPAAC reaction to obtain a silica gel material of cyclodextrin. The surface of the silica gel is modified with the ADIBO dual-functional group agent, which is subjected to click ring expansion reaction together with azide cyclodextrin or azide cyclodextrin derivatives to obtain the cyclodextrin chromatographic stationary phase. According to the reaction characteristics of copper-less catalysis, high reaction speed, high selectivity and high yield of SPAAC, the chromatographic stationary phase can be quickly and efficiently prepared and applied to chromatographic separation of chiral compounds.

Description

technical field [0001] The invention relates to the technical field of preparation of silica gel chromatographic materials. It uses silica gel as a substrate and uses Cu-free SPAAC reaction as a template. First, the ADIBO reagent containing an alkynyl functional group is modified on the surface of a silica gel stationary phase, and then combined with an azide functional group. Cyclodextrin or cyclodextrin derivatives react to obtain a cyclodextrin-modified silica gel stationary phase. Background technique [0002] Beginning in 2001, the sharpless group catalyzed an alkynyl-containing reagent and an azide functional group-containing click reaction with good selectivity and high bonding efficiency under the catalysis of Cu [1] (H.C.Kolb, M.Finn, K.B.Sharpless, Clickchemistry :diverse chemical function from a few good reactions, AngewandteChemie International Edition 40(2001)2004-2021.); For more than 10 years, the click reaction has been widely used in stationary phase surface...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30B01D15/38C08G81/00
CPCB01D15/3833B01J20/29B01J20/3085B01J2220/52C08G81/00
Inventor 梁鑫淼刘玉洁于龙付冬梅肖远胜郭志谋
Owner ACCHROM TECH (DALIAN) TECH CO LTD
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