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Organic substituted boric acid ester, boron affinity functional material using organic substituted boric acid ester as functional monomer as well as preparation and application of organic substituted boric acid ester

A borate and alcohol borate technology, which is applied in the field of new phenylboronate ligands and phenylboronic acid functionalized porous monolithic materials, can solve the problems of not reaching the scope of application and limiting applications, etc.

Inactive Publication Date: 2011-10-19
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These studies have broadened the application range of boron affinity to neutral, but have not yet reached the optimal application range
In addition, the currently existing "wulff" type of organic boronic acid has few suitable functional groups that can connect this type of substance to the carrier material, thus limiting the application of this type of organic substituted boronic acid in the field of affinity materials.

Method used

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  • Organic substituted boric acid ester, boron affinity functional material using organic substituted boric acid ester as functional monomer as well as preparation and application of organic substituted boric acid ester
  • Organic substituted boric acid ester, boron affinity functional material using organic substituted boric acid ester as functional monomer as well as preparation and application of organic substituted boric acid ester
  • Organic substituted boric acid ester, boron affinity functional material using organic substituted boric acid ester as functional monomer as well as preparation and application of organic substituted boric acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1. Synthesis of 4-amino-2-(dimethylaminomethyl)phenylboronic acid pinacol ester (Formula 4)

[0038] The first step is the synthesis of 4-nitro-2-methylphenylboronic acid pinacol ester (formula 1)

[0039] 10.02 g 4-nitro-2-methyl bromobenzene, 13.00 g pinacol diboron, 12.80 g potassium acetate, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride 0.42 The grams were put into a 500 ml three-necked flask, 220 ml dioxane was added, and the reaction was carried out at 100°C for 12 hours under the protection of nitrogen. After cooling to room temperature, 220 ml of ethyl acetate and 400 ml of water were added, and the organic layer was separated, washed with water twice, brine once, and dried with anhydrous magnesium sulfate. After filtration, it was concentrated to remove the solvent, and separated by column chromatography (EtOAc:Hexane=1:20, v / v) to obtain the compound represented by Formula 1, melting point: 46-47°C, yield 70%.

[0040] 1 H NMR (500 MHz, CDCl 3 ...

Embodiment 2

[0054] Example 2 Synthesis of monolithic materials

[0055] (1) Synthesis of capillary monolithic column: 240mg glycidyl methacrylate (GMA), 160mg polyethylene glycol diacrylate (PEGDA), 10mg azobisisobutyronitrile and 200mg dimethyl sulfoxide (DMSO) ,400mg 1,4-butanediol was mixed, vortexed and sonicated for 30 minutes, injected into the activated capillary, sealed both ends of the capillary with rubber pads, and then placed in a water bath for 18 hours at 75°C. After finishing, flush out the porogen (DMSO, dodecanol) to obtain a capillary monolithic column.

[0056] (2) Synthesis of a monolithic column of conventional size: 2.4g glycidyl methacrylate (GMA), 1.6g polyethylene glycol and acrylate (PEGDA), 50mg azobisisobutyronitrile and 2.0g dimethyl methacrylate Sulfone (DMSO), 4.0g 1,4-butanediol mixed, vortex and ultrasonic for 30 minutes, add the prepared mixed solution to a conventional column, seal both ends and put it in a water bath at 75°C After reacting for 24h, the con...

Embodiment 3

[0058] Example 3 Modification of synthetic functionalized phenylborate on the surface of monolithic column

[0059] (1) Surface modification of monolithic column materials (including capillary columns and conventional columns): take a certain amount of 3-dimethylaminomethylaniline-4-pinacol borate, dissolve it in acetonitrile, and then add a certain amount of three Ethylamine. The prepared solution was injected into the monolithic column and reacted at 60°C for 24h. After the reaction, the unreacted reagents in the monolithic column were washed out with pure acetonitrile to obtain the modified monolithic material.

[0060] (2) Surface modification of massive monoliths: Take a certain amount of 3-dimethylaminomethylaniline-4-pinacol borate, dissolve it in a certain volume of acetonitrile, and then add a certain amount of triethylamine, Then soak the block-shaped monolithic material in the above-prepared solution, and then heat it at 60°C for 24h, and then use the Soxhlet extraction...

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Abstract

The invention provides organic substituted boric acid ester which is 4-amino-2-(dimethylaminomethyl) phenylboric pinacol ester. The organic substituted boric acid ester has the following structural formula described in the specification and is characterized in that boron-nitrogen coordination exists in molecules of the organic substituted boric acid ester and the organic substituted boric acid ester contains functional groups capable of having chemical effects on the surface of a carrier material. A novel boron affinity functional material prepared by using the invention can adapt to working environments from moderate acidity to alkalinity so as to make up the defect of narrow working acidity range of a traditional boron affinity material and can be applied to the aspects like identification, immobilization, enrichment, separation, detection and the like of cis-o-dihydroxyl biomolecules under the condition of wide pH value range.

Description

Technical field [0001] The invention relates to a novel phenylboronic acid ester ligand and a phenylboronic acid functionalized porous monolithic material. Background technique [0002] Affinity is a highly specific interaction between two substances. For example, the interaction between enzymes and substrates (or inhibitors), antigens and antibodies, lectins and polysaccharides. This kind of mutual affinity exists between organic substituted boric acid and a class of compounds containing cis-ortho-dihydroxyl groups. This kind of interaction is reversible, and the occurrence and elimination of this interaction can be controlled by adjusting the pH of the environment. This force can be used to conveniently study compounds containing cis-ortho-dihydroxyl groups. A class of compounds containing cis-ortho-dihydroxyl groups, such as glycoproteins, modified nucleosides, catechols, etc., have important research value in the fields of proteomics and metabolomics. For example, glycopro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C08J7/12
Inventor 刘震李恒业
Owner NANJING UNIV
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