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A method for preparing ε-polylysine by ring-opening polymerization

A technology of polylysine and ring-opening polymerization, which is applied in the field of ring-opening polymerization to prepare ε-polylysine, which can solve the problems of low cost, limited application fields of ε-polylysine, and high production cost, and achieve low cost Effect

Active Publication Date: 2016-11-09
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

[0004] The present invention aims to solve the problem that ε-polylysine is mainly prepared by biological fermentation method in the prior art, and the production cost is relatively high. At the same time, the molecular weight of the polymer obtained by the biological fermentation method is less than 4,000 and the molecular weight cannot be adjusted, which greatly limits ε-polylysine. The technical problem in the application field of polylysine is to provide a method for preparing ε-polylysine by ring-opening polymerization, which has low cost and the molecular weight of the obtained ε-polylysine can be adjusted

Method used

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  • A method for preparing ε-polylysine by ring-opening polymerization
  • A method for preparing ε-polylysine by ring-opening polymerization
  • A method for preparing ε-polylysine by ring-opening polymerization

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preparation example Construction

[0047] (5) Preparation of formula (Ⅵ) epsilon-polylysine:

[0048] Remove the protective group from the poly(S)-α-protected amino-lysine prepared in step (4), the reaction temperature is 20°C-130°C, and the time is 1-30 days to obtain ε-polylysine ;

[0049] The deprotection solvent used is one or more of tetrahydrofuran, DMF, DMSO, methanol, ethanol, ethylene glycol dimethyl ether, chloroform, dichloromethane and water.

[0050] The deprotection method used in step (5) corresponds to that in step (3).

[0051]After the reaction is completed, the polymer is obtained by dialysis and then freeze-drying. Or directly freeze-dry, add a small amount of water to remove excess inorganic salt, and obtain the polymer after centrifugation.

Embodiment 1

[0054] (1) Preparation of L-lysine methyl ester dihydrochloride

[0055] Dry the 500ml single-necked flask, add 36.5g of L-lysine hydrochloride, add 500ml of methanol, and add 60ml of benzoyl chloride dropwise under ice-water bath conditions. After the dropwise addition, continue the reaction at room temperature for 45 minutes , then placed in a 50°C oil bath and heated for 12 hours, then cooled at room temperature overnight, crystals were precipitated, filtered, washed with ether, and vacuum-dried at 20°C for 12 hours to obtain 29.2g of L-lysine methyl ester dihydrochloride , yield 80%. 1 H NMR (DMSO-d 6 ,300MHz) δ8.69(s,2H), 8.13(s,2H), 4.05(t,J=6Hz,1H), 3.73(s,3H), 2.89(t,J=7.2Hz,2H), 1.90 -1.87 (m, J=6.8Hz, 2H), 1.60 (m, J=7.2Hz, 2H), 1.40-1.38 (m, J=6.8Hz, 2H).

[0056] (2) Preparation of (S)-α-aminocaprolactam

[0057] Dry the 500ml three-neck flask, weigh 23.3g of L-lysine methyl ester dihydrochloride, dissolve it in 320ml of methanol, add 16mL of pyridine dropwise ...

Embodiment 2

[0065] (1) Preparation of L-lysine methyl ester dihydrochloride

[0066] Dry the 500ml single-necked flask, add 36.5g of L-lysine hydrochloride, add 500ml of methanol, and add 42.8ml of thionyl chloride dropwise at -78°C for more than 1 hour. The system becomes clear first and then cloudy. After the dropwise addition, the reaction was carried out at room temperature for 30 minutes, and then placed in an oil bath at 90°C and heated to reflux for 2 hours, and the system became clear and transparent. Then it was cooled at room temperature overnight, and crystals were precipitated, filtered, and washed with diethyl ether. Vacuum drying at 20° C. for 12 hours gave 33.6 g of L-lysine methyl ester dihydrochloride with a yield of 92%. 1 HNMR (DMSO-d 6 ,300MHz) δ8.69(s,2H), 8.13(s,2H), 4.05(t,J=6Hz,1H), 3.73(s,3H), 2.89(t,J=7.2Hz,2H), 1.90 -1.87 (m, J=6.8Hz, 2H), 1.60 (m, J=7.2Hz, 2H), 1.40-1.38 (m, J=6.8Hz, 2H).

[0067] (2) Preparation of (S)-α-aminocaprolactam

[0068] Dry the...

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Abstract

The invention relates to a ring opening polymerization method for preparing epsilon-polylysine, belongs to the field of polymer synthesis methodology, and aims at solving the technical problems that existing epsilon-polylysine is mainly prepared by the biological fermentation process which is relatively high in production cost, the molecular weight of the polymer obtained by the biological fermentation process does not reach 4000, and the molecular weight cannot be adjusted, thereby greatly limiting the application field of epsilon-polylysine. The method is characterized in that a lysine monomer is ringed to obtain heptatomic ring lactam with alpha amino, and then the ring opening polymerization is performed for heptatomic ring lactam to obtain epsilon-polylysine. With the adoption of the preparation method, cheap renewable resource, namely, L-lysine is used as the starting material to effectively prepare adjustable-molecular-weight epsilon-polylysine with high additional values, the molecular weight of obtained epsilon-polylysine is 3000 to 100000, and in addition, the method is low in cost.

Description

technical field [0001] The invention relates to the field of polymer synthesis methodology, in particular to a method for preparing ε-polylysine by ring-opening polymerization. Background technique [0002] In the polymer of lysine, due to the different position of the amino group condensed with the carboxyl group, the polymer has two forms of α and ε ( figure 1 ). α-polylysine (α-PL) is obtained from the N-carboxyanhydride (NCA) monomer of lysine by ring-opening polymerization. The ring-opening polymerization of lysine NCA monomer initiated by transition metals can synthesize α-polylysine with controllable molecular weight and distribution, but the cytotoxicity of α-polylysine limits its application field. ε-polylysine (ε-PL), which is produced by microbial fermentation, is safe, non-toxic, biodegradable and has excellent antibacterial properties. It has been approved by the US Food and Drug Administration (FDA) for food preservation and preservation. Additives for cosme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/48C08G69/16
Inventor 陶友华陈霄宇贾凡李茂盛王献红
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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