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A method and application of rapid preparation of polyamino acid and its derivatives

A technology of polyamino acids and derivatives, applied in other methods of inserting foreign genetic materials, pharmaceutical formulations, bulk chemical production, etc., can solve problems such as quenching and chain transfer, harsh polymerization conditions, and large solvent consumption, and achieve solution High polarity, easy recycling, and no pollution cost effects

Inactive Publication Date: 2015-10-07
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the high reactivity of NCA monomer, it is sensitive to high temperature and humidity, and it is easy to decompose and deactivate before polymerization.
Moreover, during the polymerization process, trace amounts of water and impurities in the system can also cause side reactions such as quenching and chain transfer.
Therefore, there are many deficiencies in this preparation method: the polymerization conditions are relatively harsh, and anhydrous and oxygen-free are required; the solvent consumption is relatively large, and multiple purifications of raw materials and products are required; the reaction time is long, and it usually takes at least two to three days to obtain High monomer conversion rate
In addition, the solvents used (such as dioxane) are highly toxic, and there are also potential dangers such as damage to health and pollution of the environment.

Method used

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  • A method and application of rapid preparation of polyamino acid and its derivatives
  • A method and application of rapid preparation of polyamino acid and its derivatives
  • A method and application of rapid preparation of polyamino acid and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] S1. Preparation of L-type α-benzyl glutamate: 30 g of L-glutamic acid and 28.9 g of benzyl alcohol were mixed in a 250 ml round bottom flask, then heated to 70 °C in an oil bath, and then slowly dropped into 55 The concentrated sulfuric acid with a mass fraction of g of 66% was heated and stirred at 70°C until the solution changed from turbid to completely clear, then the round bottom flask was placed under a rotary evaporator and kept in a water bath at 60°C for 4 hours, and then the obtained The viscous liquid was slowly poured into 250 ml of ice water containing 33 g of sodium bicarbonate without excess CO 2 After release, the ice-water mixture containing the precipitate was placed in a refrigerator at 4°C for 24 hours, then filtered, and the obtained filter cake was washed with absolute ethanol for 4 hours. The white precipitate was reprecipitated 4 times with deionized water. This side is also applicable to the preparation of benzyl aspartate.

[0032] S2...

Embodiment 2

[0041] S1. Preparation of L-type α-aspartic acid benzyl ester: same as Example 1.

[0042] S2. Preparation of L-type α-aspartic acid benzyl ester-N-carboxylic acid anhydride: same as Example 1.

[0043] S3. Synthesis of poly(benzyl L-aspartate): only the ionic liquid solvent is 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4), and other steps are the same as in Example 1. The specific experimental results are shown in the table below:

[0044]

[0045] S4. Preparation of poly(L-aspartic acid) by deprotection of poly(L-aspartic acid benzyl ester): same as Example 1.

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Abstract

The invention belongs to the technical field of chemical synthesis, and in particular discloses a method for rapidly preparing polyamino acid and a derivative thereof and an application of the method. According to the method, the polyamino acid and the derivative thereof are prepared through ring-opening polymerization between L-type alpha-amino acid-N-carboxylic acid anhydride and a derivative thereof under the condition of microwave irradiation heating by adopting ionic liquid as a reaction solvent, so that the reaction time can be greatly shortened, the polymerization efficiency can be improved, and the product quality can be optimized. An ionic liquid microwave polymerization technology adopted by the method has the significant characteristics of low energy consumption, high efficiency, no pollution, low cost and capability of easily realizing continuous large-scale production, so that the application fields of the polyamino acid and the derivative thereof can be further expanded and the application values of the polyamino acid and the derivative thereof can be improved hopefully.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method and application for rapidly preparing polyamino acids and derivatives thereof. Background technique [0002] As we all know, polyamino acid materials prepared from natural amino acids have good biocompatibility, biodegradability and good mechanical properties, and can be widely used in biomedicine such as targeted drug delivery, gene transfection, tissue engineering scaffold hydrogel, etc. field. [0003] At present, the preparation methods of polyamino acids are mainly based on microbial fermentation and chemical synthesis. Among them, the microbial fermentation method has a large amount and no pollution, but it is limited to a few non-poly α-amino acids (such as γ-polyglutamic acid and ε-polylysine), and the molecular weight of the product is too large (usually 500,000 g / mol above), the distribution is too wide, it is difficult to purify, and i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/14C08G69/16A61K47/34A61L27/18C12N15/87
CPCY02P20/54
Inventor 张超胡伟康李皓曾雯蒋庆
Owner SUN YAT SEN UNIV
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