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, scientific instruments, etc. by electromagnetic means, and can solve the problems of limited solubility, limited application, and difficult solubility of derivatives

Inactive Publication Date: 2015-07-01
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0010] 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 retention degree can reach 95%. The above-mentioned properties make this product have good application prospects in enzyme-based biosensors that cooperate with electrochemical detection with enzyme catalysis; 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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Embodiment 1 (preparation of chitosan 6-OH immobilized cyclodextrin derivatives)

[0080]1 part of chitosan was weighed and dissolved 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 add methanol to precipitate the resulting chitosan derivatives, wash with ethanol more than 2 times to remove excess phthalic anhydride compounds, and then vacuum dry at 60°C to obtain phthalic anhydride-protected chitosan derivatives a .

[0081] 1 part of phthalic anhydride-protected chitosan derivative a is dissolved in 200 parts of DMSO, and 30 parts of chloroform solution of p-toluenesulfonyl chloride are added thereto, wherein the mass concentration of p-toluenesulfonyl chloride is 20% , dripped in 10 minutes, reacted at 30°C for 3 hours, filtered with suction to obtain a light yellow solid, washed away unreact...

Embodiment 2

[0087] Embodiment 2 (preparation of chitosan 6-OH immobilized cyclodextrin derivatives)

[0088] Utilize the click chemical reaction of the azide derivative c of chitosan prepared in specific example 1 and the monoalkynylation derivative e of cyclodextrin to prepare phthalic anhydride chitosan immobilized cyclodextrin derivative Object f:

[0089] Weigh 1 part of the azide derivative c of chitosan, dissolve it in 10 parts of DMAc, and weigh 0.03 parts of CuSO 4 ·5H 2 O was dispersed in 5 parts of ethanol, adding 0.03 part of sodium ascorbate and 0.05 part of water to promote dissolution, mixed the solution, weighed 4 parts of monoalkynylated derivative e, added the above solution, stirred and reacted at 60°C for 5 hours, Stop the reaction, add acetonitrile to precipitate, wash with water twice, and vacuum-dry the filter cake at 60° C. to obtain phthalic anhydride chitosan immobilized cyclodextrin derivative f.

[0090] 1 part of obtained phthalic anhydride-based chitosan im...

Embodiment 3

[0091] Embodiment 3 (use chitosan 6-OH immobilized cyclodextrin derivative of the present invention to prepare biosensor membrane material and be used for H 2 o 2 Electrochemical detection)

[0092] 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 the electron mediator ferrocene, previously dissolved in tetrahydrofuran, was added thereto. In the reaction, the molar ratio of chitosan immobilized cyclodextrin derivatives to 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 clathrate is precipitated with deionized water, the electron mediator that has not been clathrated is washed away with tetrahydrofuran, and dried to obtain a chitosan 6-OH-immobilized c...

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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 present invention relates to a kind of preparation method of chitosan 6-OH immobilized cyclodextrin derivative and its preparation method in H 2 o 2 The invention relates to the application of detection electrochemical sensor membrane materials, belonging to the field of preparation and modification of polymer materials. Background technique [0002] Chitosan is rich in sources, low in price, easy to chemically modify, can be combined with enzymes, and has excellent properties such as film-forming, biocompatibility, biodegradability, permeability, hydrophilicity, and mechanical strength. It has important application value in functional membrane materials for biosensors. [0003] In the current literature reports on the construction of sensor membranes by chitosan, mainly through 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 ele...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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