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Glycopeptides of epsilon-polylysine-grafted-hydrophobic amino acid-grafted-trehalose and preparation method

A technology of hydrophobic amino acid and polylysine, which is applied in the field of biomedical materials, can solve the problems of non-membrane permeability, etc., and achieve the effect of easy operation, good biocompatibility, and easy availability of experimental raw materials

Active Publication Date: 2019-10-18
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has also been found that trehalose can be used as a cryopreservation and freeze-drying protective agent for cells and proteins, but it is not membrane-permeable

Method used

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  • Glycopeptides of epsilon-polylysine-grafted-hydrophobic amino acid-grafted-trehalose and preparation method
  • Glycopeptides of epsilon-polylysine-grafted-hydrophobic amino acid-grafted-trehalose and preparation method
  • Glycopeptides of epsilon-polylysine-grafted-hydrophobic amino acid-grafted-trehalose and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Preparation of ε-polylysine-graft-p-toluenesulfonyl-arginine-graft-trehalose

[0026] 1) tert-butoxycarbonyl-p-toluenesulfonyl-arginine (1.07g, the amount of substance is 0.0025mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 0.479 g, 0.0025mol) was dissolved in 11 mL of dimethyl sulfoxide to obtain a solution with a concentration of tert-butoxycarbonyl-p-toluenesulfonyl-arginine of 10 wt%, and stirred for 30 min;

[0027] 2) Add ε-polylysine (0.32g, the amount of amino substances is 0.0025mol) according to the molar ratio of ε-polylysine amino group to tert-butoxycarbonyl-p-toluenesulfonyl-arginine molar ratio of 1:1 The aqueous solution was reacted at room temperature for 72 hours, and after dialysis and freeze-drying, the product ε-polylysine-graft-tert-butoxycarbonyl-graft-p-toluenesulfonyl-arginine was obtained;

[0028] 3) The obtained ε-polylysine-graft-tert-butoxycarbonyl-graft-p-toluenesulfonyl-arginine product was fully dissolved by adding trifluoro...

Embodiment 2

[0038] (1) Preparation of ε-polylysine-graft-phenylalanine-graft-trehalose

[0039] 1) tert-butoxycarbonyl-phenylalanine (1.33g, the amount of substance is 0.005mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 0.958g, 0.005mol ) was dissolved in 13 mL of dimethyl sulfoxide to obtain a solution with a concentration of tert-butoxycarbonyl-phenylalanine of 10 wt%, and stirred for 60 min;

[0040] 2) According to the amino group of ε-polylysine and tert-butoxycarbonyl-phenylalanine molar ratio 1:0.5, add ε-polylysine (0.32g, the amount of amino substance is 0.0025mol) aqueous solution and react at room temperature After 48 hours, after dialysis and freeze-drying, the product ε-polylysine-graft-phenylalanine-arginine was obtained;

[0041] 3) The obtained ε-polylysine-graft-phenylalanine-arginine product was fully dissolved by adding trifluoroacetic acid at a mass volume fraction of 15%, and stirred at room temperature for 2 hours;

[0042] 4) Precipitate with ether, collec...

Embodiment 3

[0051] (1) Preparation of ε-polylysine-graft-leucine-graft-trehalose

[0052] 1) tert-butoxycarbonyl-leucine (1.16g, the amount of substance is 0.005mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 0.479g, 0.0025mol) Dissolve in 6 mL of dimethyl sulfoxide to obtain a solution with a concentration of tert-butoxycarbonyl-leucine of 20 wt%, and stir for 45 min;

[0053] 2) According to the amino group of ε-polylysine and tert-butoxycarbonyl-leucine molar ratio 1:0.75, add ε-polylysine (0.48g, the amount of amino substance is 0.00375mol) aqueous solution and react at room temperature for 56h , after dialysis and freeze-drying, the product ε-polylysine-graft-tert-butoxycarbonyl-leucine is obtained;

[0054] 3) The obtained ε-polylysine-graft-tert-butoxycarbonyl-leucine product was fully dissolved by adding trifluoroacetic acid at a mass volume fraction of 20%, and stirred at room temperature for 4 hours;

[0055] 4) Precipitate with ether, collect the precipitate, dissolve ...

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Abstract

The invention relates to glycopeptides of epsilon-polylysine-grafted-hydrophobic amino acid-grafted-trehalose and a preparation method. The preparation method comprises the following steps: by takingepsilon-polylysine and hydrophobic amino acid as raw materials, performing a 1-(3-dimethyl amino propyl)-3-ethyl carbon diimine coupling reaction and trifluoroacetic acid deprotection so as to obtainepsilon-polylysine-grafted-p-toluenesulfonyl-arginine, epsilon-polylysine-grafted-phenylalanine, epsilon-polylysine-grafted-leucine and epsilon-polylysine-grafted-valine; and by taking epsilon-polylysine-grafted-hydrophobic amino acid and carboxylated trehalose as raw materials, performing a coupling reaction, so as to obtain a product. The method is simple and convenient in operation, low in cost, gentle in reaction condition and easy in experiment raw material. The product has good biocompatibility and cell membrane stability, has a cell cryopreservation protection anabiosis rate increased to 75.6% from 49.0%, and is applicable to the field of biomedical cell low-temperature cryopreservation and protection materials.

Description

technical field [0001] The present invention relates to a glycopeptide of ε-polylysine-grafted-hydrophobic amino acid-graft-trehalose and its preparation method, in particular to the sugar of ε-polylysine grafted with hydrophobic amino acid and carboxylated trehalose The preparation of the peptide and the application of enhancing the cryopreservation effect of red blood cells belong to the field of biomedical materials. Background technique [0002] Cryomedicine involves long-term storage of cells / proteins, which is of great significance and directly related to human health. Among them, long-term cryopreservation of blood is an urgent problem to be solved. During the freezing process of cells, the rupture of the cell membrane caused by freezing inside and outside the cells is the fatal point, and at the same time, it will denature hemoglobin. [0003] At present, the long-term storage method of cells is mainly cryopreservation under low temperature conditions by adding cryo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/48A01N1/02
CPCA01N1/0221C08G69/48
Inventor 袁晓燕刘波赵蕴慧任丽霞
Owner TIANJIN UNIV
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