Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of polyethylene carboxylic acid and its use

A technology of polyethylene glycol carboxylic acid and polyethylene glycol, which is applied in the field of protein chemistry and can solve problems such as unfavorable large-scale production, high temperature, and wide molecular weight distribution

Inactive Publication Date: 2009-06-10
INST OF PROCESS ENG CHINESE ACAD OF SCI
View PDF8 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many ways to convert alcohol into carboxylic acid, the most commonly used are the following: (1) carboxylic acid can be obtained by oxidizing polyethylene glycol with nitric acid, but the ether bond of PEG is prone to breakage during the reaction
Therefore, the molecular weight distribution of the PEG carboxylic acid that makes is wider, is unfavorable for preparing homogeneous protein modification agent, and the PEG that molecular weight is less than 400dalton has toxicity [3]
(2) Preparation of carboxylate by liquid-phase dehydrogenation of alcohol and caustic alkali in the presence of noble metal catalysts. This method has a high temperature and is easy to break the ether bond [4]
(3) Preparation of polyethylene glycol carboxylic acid with potassium permanganate oxidation under alkaline conditions [5] , but this method is also very easy to cause the breakage of the PEG ether bond
(4) Use mild oxidizing agent MnO 2 First, PEG is oxidized to PEG aldehyde, and then PEG aldehyde is oxidized to PEG carboxylic acid under the action of hydrogen peroxide. Although this method has mild conditions, the yield is low [6]
The use of organic solvents will cause environmental pollution and is not conducive to large-scale production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of polyethylene carboxylic acid and its use
  • Preparation method of polyethylene carboxylic acid and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Pour 7.5 grams of monomethoxypolyethylene glycol (mPEG, with a molecular weight of 750), 0.0078 grams of 2,2,6,6-tetramethyl-piperidine-1-oxyl group, and 0.2 grams of potassium bromide into a container In the beaker of 50 milliliters of water, magnetic stirring, ice-water bath cooling, in this beaker, pour 40 milliliters of 8% sodium hypochlorite solution (1 ℃, pH value is 10). Under ice-water bath conditions, during the reaction process, the pH value of the reaction system was adjusted to 10 with 0.5N sodium hydroxide continuously. After about 2 hours the pH didn't change any more and stabilized around 10. Then, at room temperature, stirring was continued for 6 hours, and 5 ml of ethanol was added to annihilate the reaction. The pH of the aqueous reaction solution was adjusted to 3 with 4N hydrochloric acid solution, the reaction solution was extracted three times with dichloromethane, and the extracts were combined and concentrated. Pour the concentrated solution in...

Embodiment 2

[0026] Pour 10 grams of mPEG (molecular weight of 2000), 0.0048 grams of 4-methoxy-2,2,6,6-tetramethyl-piperidine-1-oxyl group, and 0.11 grams of potassium bromide into 70 milliliters of water In the beaker, magnetic stirring, ice-water bath cooling, pour 24 milliliters of 8% sodium hypochlorite solution (1 ℃, pH value is 10) into this beaker. Under ice-water bath conditions, during the reaction, the pH of the reaction system was adjusted to 10 with 0.5N sodium hydroxide. After about 1.5 hours the pH didn't change any more and stabilized around 10. Then, at room temperature, stirring was continued for 6 hours, and 3.5 ml of ethanol was added to annihilate the reaction. The pH of the reaction solution was adjusted to 3 with 4N hydrochloric acid solution, the reaction solution was extracted three times with dichloromethane, and the three extracts were combined and concentrated. Pour the concentrated solution into cold diethyl ether, cool and precipitate, rinse with cold diethy...

Embodiment 3

[0028] Pour 20 grams of mPEG (molecular weight is 5000), 0.004 grams of 2,2,6,6-tetramethyl-piperidine-1-oxyl group, and 0.08 grams of sodium bromide into a beaker containing 120 milliliters of water, and magnetically stir , cooling in an ice-water bath, pour 13 milliliters of 8% sodium hypochlorite solution (1° C., pH 10) into the beaker. Under ice-water bath conditions, during the reaction, the pH value of the reaction system was adjusted to 10 with 0.5N sodium hydroxide. After about 2 hours the pH didn't change any more and stabilized around 10. Then, at room temperature, stirring was continued for 6 hours, and 2 ml of ethanol was added to annihilate the reaction. The pH of the reaction solution was adjusted to 3 with 4N hydrochloric acid solution, the reaction solution was extracted three times with dichloromethane, and the three extracts were combined and concentrated. Pour the concentrated solution into cold diethyl ether, cool and precipitate, rinse with cold diethyl ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A process for preparing the glycol carboxylic acid used for modifying protein or polypeptide features that the water is used as solvent, the hypohalate is used as oxidant, and the glycol is converted to glycol carboxylic acid under existance of free N-O radicals and bromide.

Description

technical field [0001] The invention belongs to the field of protein chemistry and relates to a preparation method and application of a protein modifier. Background technique [0002] Polyethylene glycol (PEG) is a synthetic polymer, a highly hydrophilic polyether, easily soluble in organic solvents and water, has good physical, chemical and physiological properties, and is non-toxic, non-antigenic and immunogenic Sex, an additive that has been approved by the FDA for entering the human body. PEG has good biocompatibility, low protein and low platelet adsorption and low cell adhesion in vivo, which make it widely used in the field of biomedicine. Linking polyethylene glycol with proteins, polypeptides, and small molecules can change the pharmacokinetics and physiological properties of these substances in the body, thereby transferring some properties of polyethylene glycol to proteins, polypeptides, and small molecules compound. For example, it can shield the antigenicity...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/48C07K17/08
Inventor 马光辉苏志国李兴奇
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI