Polyethylene glycol omega-amino acid and preparation method thereof

A polyethylene glycol and amino acid technology, which is applied in the preparation of carbamic acid derivatives, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of complex separation and low yield of monochlorination, and avoid complicated operations, The effect of novel structure and mild conditions

Inactive Publication Date: 2010-11-24
CENT SOUTH UNIV
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has mild conditions, because the hydroxyl groups at both ends of PEG have the same activity, even if the amount of reaction is strictly controlled, it will eventually be a mixture of monochlorinated, dichlorinated and unchlorinated PEG, and the yield of monochlorinated is not high, and Operations requiring complex separation

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
  • Polyethylene glycol omega-amino acid and preparation method thereof
  • Polyethylene glycol omega-amino acid and preparation method thereof
  • Polyethylene glycol omega-amino acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 6 g of polyethylene glycol (PEG, molecular weight 1000), 0.12 g of sodium bromide, and 0.01 g of TEMPO into 20 mL of water, and stir magnetically under an ice bath. Measure 26mL of sodium hypochlorite solution (available chlorine > 10%) and add 4mol·L dropwise -1 Hydrochloric acid adjusts the pH to around 10. Keep the reaction temperature and pH constant, and react for 1-2 hours. After the reaction was completed, 3 mL of ethanol was added to terminate the reaction. Drop into 4mol·L -1 Adjust the pH value to less than 2 with hydrochloric acid, add ether and wash 3 times. Dichloromethane was added for extraction, and the oil phase was rotary evaporated, then precipitated with ether, and dried in vacuum to obtain 5.93 g of α, ω-dicarboxypolyethylene glycol, with a yield of 96.1%.

[0031] 2g of dichlorotrityl chloride resin (crosslinking degree 1% DVB, substitution degree 0.95mmol·g -1 ) swelling in dichloromethane for 10min. 5 g of synthetic α,ω-dicarboxypo...

Embodiment 2

[0036] Dissolve 10 g of polyethylene glycol (PEG, molecular weight 2000), 100 mg of sodium bromide, and 8 mg of TEMPO into 20 mL, and stir magnetically under an ice bath. Measure 22mL of sodium hypochlorite solution (available chlorine > 10%) and add 4mol·L dropwise -1 Hydrochloric acid to adjust the pH to about 10. Keep the reaction temperature and pH constant, and react for 1-2h. After the reaction was completed, 3 mL of ethanol was added to terminate the reaction. Drop into 4mol·L -1 Adjust the pH value to less than 2 with hydrochloric acid, add ether and wash 5 times. Dichloromethane was added for extraction, and the oil phase was rotary evaporated, then precipitated with ether, and dried in vacuo to obtain 10.1 g of α,ω-dicarboxypolyethylene glycol with a yield of 99.2%.

[0037] Swell 2 g of dichlorotrityl chloride resin (crosslinking degree 1% DVB, substitution degree 0.95 mmol / g) in dichloromethane for 10 min. 10 g of synthesized α,ω-dicarboxypolyethylene glycol w...

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

PropertyMeasurementUnit
degree of substitutionaaaaaaaaaa
Login to view more

Abstract

The invention belongs to the technical field of macromolecular synthetic chemistry, and particularly relates to polyethylene glycol omega-amino acid and a preparation method thereof. The method comprises the following steps of: oxidizing hydroxys at two ends of polyethylene glycol into carboxyls, loading the polyethylene glycol of which the end groups are the carboxyls to resin by nucleophilic substitution reaction, and protecting the free carboxyls through methyl ester; and cracking the double-carboxyl polyethylene glycol of which one end is protected by the methyl ester from the resin, and then modifying the free carboxyls by azidation reaction and Curtius rearrangement reaction to obtain tert-butyloxycarbonyl protected amino. The method overcomes the defect that the conventional method for synthesizing the polyethylene glycol omega-amino acid has complex separation and purification. Because of the adoption of solid-phase reaction, azidation reaction and Curtius rearrangement reaction, the method has the advantages of mild condition, short synthetic route and simple separation and purification, and the yield reaches over 70 percent. The polyethylene glycol omega-amino acid can be widely applied to the fields of targeted medicament synthesis, biological sensing, immunoassay, polypeptide synthesis and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis chemistry, and relates to a polyethylene glycol omega-amino acid and a preparation method. Background technique [0002] Polyethylene glycol ω-amino acid, that is, the two ends of the polyethylene glycol (PEG) chain are amino and carboxyl respectively, and the amino and carboxyl can be respectively connected with two molecules with different characteristics. After the compound is covalent with PEG, some excellent properties of PEG can be obtained. For example, as a biological material, increasing the apparent molecular weight of its compound can reduce kidney filtration, reduce the recognition of the immune system and enzyme hydrolysis, prolong the half-life of the compound in the body; at the same time increase the water solubility of the compound and change the biological distribution, etc. Therefore, polyethylene glycol ω-amino acids can be widely used in the fields of targeted drug ...

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 Applications(China)
IPC IPC(8): C08G65/333C07C271/16C07C269/00
Inventor 刘又年陈万松郝远强张春晓
Owner CENT SOUTH UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products