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Tolyltriazole-containing polyethylene glycol protein modifier, preparation method thereof and application thereof

A protein modification, polyethylene glycol technology, applied in the preparation methods of peptides, chemical instruments and methods, organic chemistry, etc., can solve problems such as large differences between each other, cumbersome preparation methods, and unfavorable large-scale production of enterprises, and achieve cost The effect of low cost, simple process and convenient industrial production

Active Publication Date: 2012-09-19
NANJING WELL CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Technical problem: the purpose of the present invention is to overcome the shortcomings of the traditional polyethylene glycol protein modifier preparation method is too cumbersome, the difference between each other is not conducive to large-scale production of enterprises, to provide a polyethylene glycol containing triazole Alcohol protein modifier and its preparation method and application

Method used

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  • Tolyltriazole-containing polyethylene glycol protein modifier, preparation method thereof and application thereof
  • Tolyltriazole-containing polyethylene glycol protein modifier, preparation method thereof and application thereof
  • Tolyltriazole-containing polyethylene glycol protein modifier, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: with mPEG 5000 (M.W.5000) as the starting material for the preparation of mPEG 5000 -NHS (A is 0), its preparation steps are:

[0041] 1. Preparation of p-tosylated mPEG 5000 -OTs: 20g mPEG 5000Dissolve in 20ml of dichloromethane, add 400mg of triethylamine, 50mg of p-dimethylaminopyridine and 3.8g of p-toluenesulfonyl chloride under stirring condition. The reaction solution was stirred at room temperature for 24 hours, then diluted with 200ml of dichloromethane, washed once with 100ml of cold 4M hydrochloric acid and 100ml of water, and finally dried over anhydrous sodium sulfate. The filtered organic solution was concentrated to about 30ml, and then slowly added dropwise to 400ml of anhydrous ether, and a large amount of white precipitates precipitated out. The precipitate was filtered and vacuum-dried to obtain the target product mPEG 5000 -OTs 19.5g.

[0042] 2. Preparation of Azidated mPEG 5000 -N 3 : 10g mPEG 5000 -OTs was dissolved in 50ml of ...

Embodiment 2

[0044] Example 2: Using mPEG 5000 (M.W.5000) as the starting material for the preparation of mPEG 5000 -NHS (A is 4), its preparation steps are:

[0045] 1. Preparation of p-tosylated mPEG 5000 -OTs: 20g mPEG 5000 Dissolve in 20ml of dichloromethane, add 400mg of triethylamine, 50mg of p-dimethylaminopyridine and 3.8g of p-toluenesulfonyl chloride under stirring condition. The reaction solution was stirred at room temperature for 24 hours, then diluted with 200ml of dichloromethane, washed once with 100ml of cold 4M hydrochloric acid and 100ml of water, and finally dried over anhydrous sodium sulfate. The filtered organic solution was concentrated to about 30ml, and then slowly added dropwise to 400ml of anhydrous ether, and a large amount of white precipitates precipitated out. The precipitate was filtered and vacuum-dried to obtain the target product mPEG 5000 -OTs 19.5g.

[0046] 2. Preparation of Azidated mPEG 5000 -N 3 : 10g mPEG 5000 -OTs was dissolved in 50ml o...

Embodiment 3

[0048] Example 3: Using mPEG 5000 (M.W.5000) as the starting material for the preparation of mPEG 5000 -NHS (A is 10), its preparation steps are:

[0049] 1. Preparation of p-tosylated mPEG 5000 -OTs: 20g mPEG 5000 Dissolve in 20ml of dichloromethane, add 400mg of triethylamine, 50mg of p-dimethylaminopyridine and 3.8g of p-toluenesulfonyl chloride under stirring condition. The reaction solution was stirred at room temperature for 24 hours, then diluted with 200ml of dichloromethane, washed once with 100ml of cold 4M hydrochloric acid and 100ml of water, and finally dried over anhydrous sodium sulfate. The filtered organic solution was concentrated to about 30ml, and then slowly added dropwise to 400ml of anhydrous ether, and a large amount of white precipitates precipitated out. The precipitate was filtered and vacuum-dried to obtain the target product mPEG 5000 -OTs 19.5g.

[0050] 2. Preparation of Azidated mPEG 5000 -N 3 : 10g mPEG 5000 -OTs was dissolved in 50ml ...

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Abstract

The invention discloses a tolyltriazole-containing polyethylene glycol protein modifier, a preparation method thereof and the application thereof, wherein the tolyltriazole-containing polyethylene glycol protein modifier has the following chemical general formula, wherein A is linear-chain alkyl group of which the carbon atom number is 0-20. The preparation method of the modifier comprises the following step of carrying out copper-catalyzed click chemistry on azide group-containing methoxy polyethyleneglycol and terminal acetylene link and succinimide-containing alkane derivative. The tolyltriazole-containing polyethylene glycol protein modifier provided by the invention can be used for modifying the hemoglobin, particularly used for modifying the bovine hemoglobin and the hemoglobin from human blood for human body. According to the method of the copper-catalyzed click chemistry, various functional groups can be effectively modified, and the invention is simple in technology, low in cost, and convenient for industrial production.

Description

technical field [0001] The invention relates to a protein modifier, in particular to a kind of polyethylene glycol protein modifier, a preparation method and its application. Background technique [0002] Protein drugs are mainly divided into peptides and genetically engineered drugs, genetically engineered antibodies, monoclonal antibodies, and recombinant vaccines. Compared with traditional organic small molecule drugs, protein drugs have the characteristics of high activity, low toxicity, strong specificity, clear biological function, and favorable clinical application. Because of its low cost, high success rate, safety and reliability, it has become an important part of pharmaceutical products. Since 1982 when Lilly Company of the United States put the world's first recombinant protein drug, recombinant insulin, on the market, the technological innovation and industrial development of biomedicine, especially protein drugs, have advanced by leaps and bounds. There are n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48C07K1/107
Inventor 杨洪徐顺奇姚丹陶平洋张飞林保平吴仁荣高正松贾建国沈德渊
Owner NANJING WELL CHEM
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