Preparation method of polynorbornene skeleton sugar polymer and its application in the synthesis of fucoidan sulfate mimics

A technology of fucoidan sulfate and polynorbornene, which is applied in the field of polymer material synthesis and preparation, and achieves the effects of large molecular weight, simple preparation method, and narrow molecular weight distribution range

Active Publication Date: 2020-03-27
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, sugar-containing norbornene-based polymers and their preparation methods have not been reported, and their application in the synthesis of Fucoidan mimics has not yet been reported.

Method used

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  • Preparation method of polynorbornene skeleton sugar polymer and its application in the synthesis of fucoidan sulfate mimics
  • Preparation method of polynorbornene skeleton sugar polymer and its application in the synthesis of fucoidan sulfate mimics
  • Preparation method of polynorbornene skeleton sugar polymer and its application in the synthesis of fucoidan sulfate mimics

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Experimental program
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Embodiment 1

[0036] Embodiment 1: the preparation of glucose monomer

[0037] Such as figure 1 As indicated, weigh 110.0 mg (0.44 mmol) of azide ethanolated glucose in a round bottom flask, add 4 ml THF / H 2 Dissolved in O (1:1), add 138.8mg (0.66mmol) of propargyl aminated exo-norbornene anhydride, add 868.3μl (0.088mmol, 25mg / ml) of copper sulfate pentahydrate, and 929.9μl of sodium ascorbate ( 0.528mmol, 100mg / ml), react at room temperature for 12h, evaporate the reaction solution to dryness, and obtain pure glucose monomer by column chromatography.

Embodiment 2

[0038] Embodiment 2: the preparation of mannose monomer

[0039] Such as figure 2 As indicated, weigh 110.0 mg (0.44 mmol) of azide ethanolated mannose in a round bottom flask, add 4 ml THF / H 2 Dissolved in O (1:1), add 38.8mg (0.66mmol) of propargyl-aminated exo-norbornene anhydride, add 868.3μl (0.088mmol, 25mg / ml) of copper sulfate pentahydrate, and 929.9μl of sodium ascorbate ( 0.528mmol, 100mg / ml), react at room temperature for 12h, evaporate the reaction solution to dryness, and obtain pure mannose monomer by column chromatography.

Embodiment 3

[0040] Embodiment 3: Preparation of polynorbornene-based glucose homopolymer (p-Glu)

[0041] Take 10 mg of pure glucose monomer in Example 1 in a microwave reaction tube, add 11 mg of phase transfer catalyst DTAB, add 600 μl of bis-Tris buffer and dichloroethane, add 174 μl of catalyst Hoveyda-Grubbs 2 nd , stirred at room temperature to form a stable emulsion state, placed in a microwave reactor for 5 minutes, added excess vinyl ether to terminate the reaction, and the reaction solution was directly separated and purified with LH-20, the eluent used was double distilled water, collected samples, double Distilled water dialyzed for 3 days, freeze-dried to obtain polynorbornene-based glucose homopolymer p-Glu, its H NMR spectrum is as follows: image 3 As shown, its molecular weight analysis spectrum is as Figure 4 shown. Depend on image 3 It can be seen that the chemical shift of the glucose anomeric hydrogen occurs around 4.25 ppm, proving the presence of glucose in the...

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Abstract

The invention belongs to the technical field of synthesis and preparation of high molecular materials and in particular relates to a preparation method of a polynorbornene framework sugar polymer andapplication thereof in synthesis of a fucoidan sulfate simulant. The preparation method comprises the following steps: firstly, enabling protection-free sugar with an azido functional group and alkynylated norbornene acid anhydride to be subjected to click reaction to obtain a sugar monomer; then putting the monomer into an emulsion system composed of a buffering solution / organic phase / phase transfer catalyst and catalyzing olefin to be subjected to complex decomposition ring-opening polymerization reaction by adopting a Crubbs type catalyst under microwave-assisted heating; stopping the reaction through vinyl ethyl ether; carrying out gel column separation and dialysis to obtain the polymer. According to the preparation method provided by the invention, a homopolymer and a block polymer are prepared and the obtained polymer has the advantages of large molecular weight and narrow molecular weight distribution range and a structure similar with a natural polysaccharide compound. By adopting the method provided by the invention, the fucoidan polymer with different sulfating sites can be synthesized and is used for simulating the structure and function of ocean-derived fucoidan sulfate.

Description

technical field [0001] The invention belongs to the technical field of synthesis and preparation of polymer materials, and in particular relates to a preparation method of a polynorbornene skeleton sugar polymer and its application in the synthesis of fucoidan sulfate simulants. Background technique [0002] Carbohydrates are the most widely distributed and most abundant substances in nature, and most of them exist in the body in the form of macromolecules. They are the third important bioactive macromolecules after nucleic acids and proteins. Sugar polymer is a kind of macromolecular compound in which sugar compounds are covalently linked to the polymer backbone. Its molecular weight is similar to that of natural sugar-containing macromolecules. The monomer structure of the polymer has a "multivalent effect", which can increase the affinity between the basic active unit and the protein, and achieve an activity level similar to that of natural sugar-containing macromolecules...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F132/08C08F232/08
CPCC08F132/08C08F232/08
Inventor 蔡超于广利凡飞李国云
Owner OCEAN UNIV OF CHINA
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