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Preparation method of chitosan 6-OH immobilized cyclodextrin derivative and application of derivative in H2O2 detection electrochemical sensor film material

A technology of chitosan derivatives and 6-OH, which is applied in the direction of material analysis, analytical materials, and scientific instruments through electromagnetic means, and can solve problems such as limited applications, limited solubility of derivatives, and difficult solubility

Inactive Publication Date: 2013-05-15
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The cyclodextrin immobilization rate of the product prepared by this method can reach 210 μmol g -1 Above, chitosan 2-NH 2 It has good retention, and the degree of retention can reach 95%. The above properties make this product have a good application prospect in enzyme-based biosensors that use enzyme catalysis and electrochemical detection; however, the derivatives prepared by this method are in water Limited solubility, difficult to dissolve in organic solvents, limiting its application in this field

Method used

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  • Preparation method of chitosan 6-OH immobilized cyclodextrin derivative and application of derivative in H2O2 detection electrochemical sensor film material
  • Preparation method of chitosan 6-OH immobilized cyclodextrin derivative and application of derivative in H2O2 detection electrochemical sensor film material
  • Preparation method of chitosan 6-OH immobilized cyclodextrin derivative and application of derivative in H2O2 detection electrochemical sensor film material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1 (Preparation of chitosan 6-OH immobilized cyclodextrin derivative)

[0082] Weigh 1 part of chitosan and dissolve it in 200 parts of acetic acid / water solution with a mass concentration of 1%. Dissolve 2 parts of phthalic anhydride in 50 parts of ethanol and add dropwise to the reaction system, and stir and react at 50° C. for 5 hours. Then methanol was added to precipitate the chitosan derivative produced, washed with ethanol for more than two times to remove excess phthalic anhydride compounds, and then dried under vacuum at 60°C to obtain the phthalic anhydride-protected chitosan derivative a .

[0083] Dissolve 1 part of phthalic anhydride-protected chitosan derivative a in 200 parts of DMSO, and add 30 parts of p-toluenesulfonyl chloride solution in chloroform, wherein the mass concentration of p-toluenesulfonyl chloride is 20% After dripping in 10 minutes, react at 30°C for 3 hours, and filter with suction to obtain a light yellow solid, wash off the unreac...

Embodiment 2

[0089] Example 2 (Preparation of chitosan 6-OH immobilized cyclodextrin derivative)

[0090] The click chemistry reaction of the azide derivative c of chitosan prepared in Example 1 and the monoalkynylated derivative e of cyclodextrin was used to prepare phthalic anhydride chitosan immobilized cyclodextrin derivatization F:

[0091] Weigh 1 part of the azide derivative c of chitosan, dissolve it in 10 parts of DMAc, and weigh out 0.03 parts of CuSO 4 ·5H 2 Disperse O in 5 parts of ethanol, add 0.03 part of sodium ascorbate and 0.05 part of water to promote dissolution, mix the solution, weigh 4 parts of mono-alkynylated derivative e, add the above solution, stir and react at 60°C for 5 hours, The reaction was stopped, acetonitrile was added for precipitation, washed twice with water, and the filter cake was vacuum dried at 60° C. to obtain the phthalic anhydride chitosan immobilized cyclodextrin derivative f.

[0092] Soak 1 part of phthalic anhydride chitosan immobilized cyclodextr...

Embodiment 3

[0093] Example 3 (Using the chitosan 6-OH immobilized cyclodextrin derivative of the present invention to prepare a biosensor membrane material and use it in H 2 O 2 Electrochemical detection)

[0094] The chitosan-immobilized cyclodextrin derivative obtained in Example 1 was dissolved in DMAc, wherein the concentration of the chitosan-immobilized cyclodextrin derivative in the solution was 0.025 mol / L. A solution of ferrocene, an electron mediator previously dissolved in tetrahydrofuran, is added to it. In the reaction, the molar feed ratio of the chitosan-immobilized cyclodextrin derivative and ferrocene was 1:1, and the molar concentration of ferrocene in tetrahydrofuran was 1.0 mol / L. The reaction was stirred and refluxed in an oil bath at 70°C for 8 hours. After the reaction is completed, the inclusion compound is precipitated with deionized water, the electronic mediator that has not been included is washed away with tetrahydrofuran, and dried to obtain the product of chit...

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Abstract

The invention relates to a preparation method of a chitosan 6-OH immobilized cyclodextrin derivative and an application of the derivative in an H2O2 detection electrochemical sensor film material, and belongs to the fields of preparation and modification of a high molecular material. The chitosan 6-OH immobilized cyclodextrin derivative which has an excellent solubility and high immobilization rate in water and partial organic solvents is prepared by the steps of: protecting chitosan 2-NH2 through phthalic anhydride, immobilizing cyclodextrin on a 6-OH position through a click chemical reaction, and removing protection of the chitosan 2-NH2 through hydrazine hydrate. According to the prepared chitosan 6-OH immobilized cyclodextrin derivative disclosed by the invention, an electronic mediator is immobilized in the cyclodextrin hydrophobic cavity, and 2-NH2 of a chitosan pyranoid ring is immobilized with catalase and is modified on the surface of a glassy carbon electrode, thereby forming an electrochemical biosensor film material for detecting content of H2O2. The invention makes application of the chitosan 6-OH immobilized cyclodextrin derivative in an enzyme-base biosensor combining an enzyme catalytic action and an electrochemical reaction to be possible.

Description

Technical field [0001] The invention relates to a preparation method of chitosan 6-OH immobilized cyclodextrin derivative and its application in H 2 O 2 The application in the detection of electrochemical sensor membrane materials belongs to the field of preparation and modification of polymer materials. Background technique [0002] Due to its abundant sources, low price, easy chemical modification, chitosan can be combined with enzymes, has good film-forming properties, biocompatibility, biodegradability, permeability, hydrophilicity, mechanical strength and other excellent properties. It has important application value in functional membrane materials for biosensors. [0003] The current literature reports on the construction of sensor membranes by chitosan mainly use the 2-NH of chitosan 2 Realize the immobilization of the enzyme, and promote the transfer of electrons between the electrode and the enzyme through the doping of the electroactive material (electronic mediator) and...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08B37/08C08B37/16G01N27/333
Inventor 陈煜叶彦春李伟萍郭燕文
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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