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Method for preparing polylysine of high-content linear epsilon-polylysine through pyrocondensation polymerization

A technology of polylysine and high content is applied in the field of polylysine with high content of linear ε-polylysine prepared by thermal polycondensation, which can solve the problem of low content of linear ε-polylysine and achieve simple operation. The effect of easy operation, low cost and good application value

Active Publication Date: 2018-09-04
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to solve the problem of low content of linear ε-polylysine in the branched polylysine synthesized by thermal condensation polymerization in the prior art, and to provide a method for preparing high-content linear ε-polylysine by thermal condensation polymerization. Amino acid polylysine method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] (1), preparation of α-benzaldehyde protection-lysine monomer

[0047] In a 100mL single-necked round bottom flask, add 5g of lysine monohydrochloride, add 35mL of water to dissolve, then add 1.08g of sodium hydroxide, drop in 2.9mL of benzaldehyde under ice-water bath conditions, after the dropwise addition, vigorously stir the reaction After 2 hours, the product precipitated out. The filtrate was removed by suction filtration. The product was washed with cold ethanol and dried under vacuum for 12 hours to obtain the white target product α-benzaldehyde-protected-lysine monomer (4.78g, 75%). 1 H NMR (DMSO-d 6 ,300MHz)δ1.19-1.31(m,2H),1.38(s,2H),1.53-1.65(m,2H),1.81-2.00(m,2H),2.66-2.72(t,2H),4.19- 4.25(t,2H),7.51-7.59(m,3H),7.74-7.79(m,2H),8.67(s,1H).

[0048] (2), preparation of high linear ε-polylysine content polylysine

[0049] Grind 4.68 g of α-benzaldehyde-protected-lysine monomer with 0.8 g of sodium hydroxide in a mortar, then place the mixture in a Schlenk tu...

Embodiment 2

[0051] (1), α-tert-butoxycarbonyl protection-preparation of lysine monomer

[0052] In a 100mL single-necked round bottom flask, add 5g of lysine monohydrochloride, add 20mL of water to dissolve, then add 1.2g of sodium hydroxide, under ice-water bath conditions, drop 20mL of tetrahydrofuran solution containing 3.0g of di-tert-butyl dicarbonate , after the dropwise addition was completed, the mixture was stirred and reacted at room temperature for 24 hours. After the reaction was completed, the mixture was extracted, spin-dried, and subjected to column chromatography to obtain the target product α-tert-butoxycarbonyl-protected-lysine monomer (5.31g, 80%). 1 H NMR (D 2 O,300MHz)δ1.12(s,2H),1.22-1.31(m,2H),1.42(s,9H),1.47-1.60(m,2H),1.73-1.86(m,2H),2.66-2.72 (t,2H),4.53-4.57(t,1H),5.49(s,1H).

[0053] (2), preparation of high linear ε-polylysine content polylysine

[0054] Grind 3.69 g of α-tert-butoxycarbonyl-protected-lysine monomer with 0.84 g of potassium hydroxide in a m...

Embodiment 3

[0056] (1), α-benzyloxycarbonyl protection-preparation of lysine monomer

[0057] In a 100mL single-necked round bottom flask, add 5g of lysine monohydrochloride, add 20mL of water to dissolve, then add 1.5g of potassium hydroxide, under ice-water bath conditions, drop into 20mL of tetrahydrofuran solution containing 5.1g of benzyl chloroformate, drop After the addition, the reaction was stirred at room temperature for 24 hours. After the reaction, extraction was performed, spin-dried, and recrystallized to obtain the target product α-benzyloxycarbonyl-protected-lysine monomer (5.3 g, 70%). 1 H NMR (D 2 O,300MHz)δ1.10(s,2H),1.18-1.31(m,2H),1.48-1.60(m,2H),1.74-1.84(m,2H),2.66-2.72(t,2H),4.52 -4.57(t,1H),5.05(s,2H),5.52(s,1H),7.33(s,5H).

[0058] (2), preparation of high linear ε-polylysine content polylysine

[0059] Grind 4.2 g of α-benzyloxycarbonyl-protected-lysine monomer with 0.36 g of lithium hydroxide in a mortar, then place the mixture in a Schlenk tube, heat to 150...

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Abstract

The invention provides a method for preparing polylysine of high-content linear epsilon-polylysine through pyrocondensation polymerization, belonging to the field of polymer synthesis and antibacterial materials. The method is used for solving the problem that in the prior art, linear epsilon-polylysine content in branched polylysine synthesized by the pyrocondensation polymerization is relativelylow. The method comprises the following steps of protecting alpha amidogen of lysine by using a dynamic protecting group firstly, so as to prepare a lysine monomer protected by the dynamic protectinggroup, wherein the dynamic protecting group is a protecting group capable of forming unstable amido linkage and imine linkage with the alpha amidogen of the lysine; then grinding and uniformly mixingthe lysine monomer protected by the dynamic protecting group with alkali, and adding a catalyst to react to obtain the polylysine of the high-content linear epsilon-polylysine. According to the preparation method provided by the invention, cheap and renewable lysine is used as a starting raw material, the cost is low, the operation is simple and easy to perform, and in the obtained branched polylysine, the content of the linear epsilon-polylysine can exceed 80%.

Description

technical field [0001] The invention belongs to the field of polymer synthesis and antibacterial materials, and in particular relates to a method for preparing polylysine with high content of linear ε-polylysine through thermal condensation polymerization. Background technique [0002] ε-polylysine is a cationic polyamino acid formed by linking ε-amino and α-carboxyl groups of lysine monomers. It is safe, non-toxic, biodegradable and has excellent antibacterial properties. It has been widely used in Food preservatives and cosmetic additives and other fields. The current commercialized ε-polylysine is mainly derived from microbial fermentation, and its production process is complicated, the cost is high and the molecular weight is low (less than 4000), which limits its application. [0003] On the other hand, in recent years, the production of amino acids has developed a new situation of vigorous development. Taking lysine as an example, in China alone, the annual output of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/10
CPCC08G69/10
Inventor 陶友华陈金龙王献红
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI