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Poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer, functional segmented copolymer and preparation method

A technology of block copolymer and glutamic acid ester, applied in the field of polymers, can solve the problems of polyamino acid main chain breakage and low reactivity, etc.

Active Publication Date: 2013-02-20
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The method for preparing side-group-functionalized polyamino acids through condensation reaction and transesterification reaction has low reactivity, and when the side groups are functionalized, the main chain of the polyamino acid is likely to be broken, and it is easy to be affected by functionalized unit. The influence of the molecular weight and steric hindrance of the body is limited in the application in the biomedical field

Method used

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  • Poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer, functional segmented copolymer and preparation method
  • Poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer, functional segmented copolymer and preparation method
  • Poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer, functional segmented copolymer and preparation method

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preparation example Construction

[0063] The invention provides a kind of preparation method of poly(γ-propargyl-L-glutamate)-polyamino acid block copolymer, comprising the following steps:

[0064] γ-propargyl-L-glutamic acid ester-N-internal carboxylic anhydride, amino acid-N-internal carboxylic anhydride and primary amine initiator are polymerized in anhydrous solvent to obtain poly(γ-propargyl- L-glutamate)-polyamino acid block copolymer;

[0065] The number of primary amines of the primary amine initiator is 1 to 2, and the molecular weight of the primary amine initiator is 50 to 1000;

[0066] The amino acid-N-internal carboxylic anhydride is γ-benzyl-L-glutamate-N-internal carboxylic anhydride, γ-propynyl-L-glutamate-N-internal carboxylic anhydride, γ- 2-Chloroethyl-L-glutamate-N-endocarboxylic anhydride, glycine-N-endocarboxylic anhydride, L-alanine-N-endocarboxylic anhydride, L-valine-N-endocarboxylic anhydride , L-leucine-N-endocarboxylic anhydride, L-isoleucine-N-endocarboxylic anhydride, L-phenyl...

Embodiment 1~5

[0101] Weigh 0.1056g (0.0005mol), 0.1056g (0.0005mol), 0.1056g (0.0005mol), 2.1117g (0.01mol), 4.2234g (0.02mol) of γ-propynyl-L-glutamate -N-internal carboxylic acid anhydride was placed in 5 anhydrous reaction flasks, and 5 mL of anhydrous N,N-dimethylformamide was added to dissolve the monomers. Then 10.119mg (0.0001mol) of n-hexylamine were added thereto under stirring, and the resulting mixed solution was stirred and reacted at 25°C for 72h, and then 0.1316g (0.0005mol), 2.6325g (0.01 mol), 5.265g (0.02mol), 2.6325g (0.01mol), 2.6325g (0.01mol) of γ-benzyl-L-glutamate-N-internal carboxylic acid anhydride, continue to react for 72h, after the end of the reaction , the reaction system was settled with 50mL ether, filtered, washed three times with ether, and dried in vacuum at 25°C for 24h to obtain the reaction product.

[0102] The present invention carries out structural identification to the product that obtains, and the result is as follows figure 1 as shown, figure ...

Embodiment 6~10

[0110] Take respectively poly(γ-propargyl-L-glutamate)-poly(γ-benzyl-L-glutamate) block copolymer 0.1g that embodiment 1~5 obtains, its Dissolve in 1mL of dichloroacetic acid at 25°C, and then add 0.3mL of a mixed solution of hydrogen bromide and glacial acetic acid with a mass percentage of hydrogen bromide of 33% under stirring to obtain a reaction mixture, and mix the obtained reaction The solution was stirred at 25° C. for 1 h to obtain a reaction solution. The resulting reaction solution was settled with 15 mL of ether, filtered, washed three times with ether, and dried under vacuum at 25° C. for 24 h to obtain a reaction product.

[0111] In the present invention, the obtained reaction product is detected by proton nuclear magnetic resonance spectrum, and the results are as follows: figure 2 as shown, figure 2 It is the H NMR spectrum of the block copolymer obtained in Example 7 of the present invention. Depend on figure 2 It can be seen that 5.17ppm~5.07ppm is th...

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Abstract

The invention provides poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer. The poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer is presented as the formula (I). Small molecules containing primary amino radical serve as an initiator, and the poly (gamma-propargyl-L-glutamate)-polyamino acid segmented copolymer is obtained through the gradual ring cleavage reaction of gamma- propargyl-L-glutamate-N-carboxylic acid anhydride and amino acid-N- carboxylic acid anhydride. The side chain of the segmented copolymer is propargyl which is easy to modify, has high reactivity and is beneficial to functional small molecules which are subjected to bonded azide and have biological activity or environmental responsiveness, and the bonding process cannot lead to the breakage of amino acid backbones and is not affected by the amount and steric hindrance of functional small molecules. The segmented copolymer has good biocompatibility after being functionalized and can be applied in fields such as targeted drug delivery, organizational projects and protein separation and detection.

Description

technical field [0001] The invention relates to the technical field of polymers, in particular to a poly(γ-propargyl-L-glutamate)-polyamino acid block copolymer, a functionalized block copolymer and a preparation method. Background technique [0002] Polyamino acid has a stable structure similar to natural proteins and peptides, as well as excellent degradation performance and biocompatibility, making it have broad application prospects in the field of biomedicine. In particular, since the 1990s, the discovery of controllable polymerization of NCA and the successive discoveries of various efficient "click" reactions have made the acquisition of controllable structure and functionalized polyamino acids a research hotspot, which has further promoted the development of polyamino acids. Practical application research of amino acid materials. [0003] In addition to the structural properties of the material itself, the side chain structure is an important factor affecting the pe...

Claims

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Application Information

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IPC IPC(8): C08G69/08C08G69/48A61K47/48A61K47/34A61K31/704A61P35/00
Inventor 庄秀丽丁建勋陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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