CN113150272B - Synthesis method of novel polypeptide compound - Google Patents
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- CN113150272B CN113150272B CN202110522861.6A CN202110522861A CN113150272B CN 113150272 B CN113150272 B CN 113150272B CN 202110522861 A CN202110522861 A CN 202110522861A CN 113150272 B CN113150272 B CN 113150272B
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Abstract
The invention relates to the technical field of polypeptide, and discloses a novel polypeptide compound, BOC-isoleucine-based polyamino acid is subjected to BOC removal treatment in an ethyl acetate and concentrated hydrochloric acid system to prepare isoleucine-based polyamino acid, finally, in a trifluoroacetic acid, hydrobromic acid and glacial acetic acid system, a benzyloxycarbonyl structure in a molecular structure is hydrolyzed to generate amino to obtain the novel polypeptide compound, the obtained polypeptide compound is prepared by a novel efficient synthesis method, and through experimental tests of a bacteriostatic circle method, the novel polypeptide compound has excellent antibacterial activity on bacteria and microorganisms such as salmonella, and the side chain of the novel polypeptide compound contains a hydrophobic long alkyl chain, has good hydrophobicity, can endow the polypeptide compound with excellent anticoagulant activity, and has wide application prospects in the fields of antibacterial materials, medical dressings and the like.
Description
Technical Field
The invention relates to the technical field of polypeptides, in particular to a synthesis method of a novel polypeptide compound.
Background
The polypeptide compound is a compound obtained by dehydrating and condensing amino acid molecules, is widely existed in the aspects of hormone, reproduction and the like of a human body, can regulate the physiological functions of a human system and cells in the human body, can synthesize and regulate the functional activities of the cells, is an important physiological regulator of the human body, has important biological functions, has the effects of antibiosis, health care and the like, and is widely applied in the aspects of medicine, cosmetics, health care food and the like.
In recent years, the synthesis and development of bioactive polypeptide compounds have become a research trend, and generally, the polypeptide compounds can be synthesized by amino acid micromolecule polymerization, polypeptide enzymolysis, microbial fermentation and other modes, and CN108383975B, "a preparation method of antibacterial polypeptide modified polyurethane nano-film", discloses that the antibacterial polypeptide modified polyurethane resin has excellent biological safety and antibacterial effect, so that the preparation of bioactive polypeptide compounds by a chemical synthesis method, the expansion of the actual application in the fields of antibacterial materials, medical dressings and the like, and the preparation method has important practical significance.
Disclosure of Invention
Solves the technical problem
Aiming at the defects of the prior art, the invention provides a synthesis method of a novel polypeptide compound, and the prepared polypeptide compound has excellent antibacterial property and bioactivity through a novel high-efficiency chemical synthesis method, and has wide application prospect in the fields of antibacterial materials, medical dressings and the like.
Technical scheme
In order to achieve the purpose, the invention provides the following technical scheme: a novel polypeptide compound is synthesized by the following steps:
(1) adding a mixed solvent of dichloromethane and N, N-dimethylformamide, N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and hexadecylamine into a reaction container, stirring and dissolving, carrying out polymerization reaction, carrying out reduced pressure distillation after the reaction to remove the solvent, adding distilled water, and placing into a dialysis bag for dialysis and purification to obtain hexadecyl polyamino acid with a structural formula of
；
(2) Adding N, N-dimethylformamide, hexadecyl polyamino acid and BOC-L-isoleucine into a reaction container, stirring and dissolving, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide, heating for reaction, adding distilled water into the solution after the reaction, dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid with the structural formula shown in the specification
；
(3) Adding ethyl acetate into a reaction container, dropwise adding concentrated hydrochloric acid and BOC-isoleucine-based polyamino acid, stirring at 15-30 ℃ for 2-5 h, removing BOC, extracting the solution with distilled water, taking an ethyl acetate organic phase, distilling under reduced pressure, adding an ethanol solvent into the product, placing the product into a dialysis bag, dialyzing and purifying to obtain the isoleucine-based polyamino acid with the structural formula shown in the specification
；
(4) Adding trifluoroacetic acid, hydrobromic acid and glacial acetic acid into a reaction vessel, then adding isoleucine-based polyamino acid, stirring and hydrolyzing at 15-30 ℃ for 8-20 h, adding distilled water for dilution after reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis purification to obtain a novel polypeptide compound, wherein the structural formula is shown in the specification
。
Preferably, the mass ratio of the dichloromethane, the N, N-dimethylformamide, the N6-benzyloxycarbonyl-L-lysine cyclic anhydride and the hexadecylamine in the step (1) is 3500-6000:800-1500:100: 3-8.
Preferably, the temperature of the polymerization reaction in the step (1) is 35-50 ℃, and the reaction time is 24-72 h.
Preferably, the mass ratio of the N, N-dimethylformamide, the hexadecyl polyamino acid, the BOC-L-isoleucine, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and the N-hydroxysuccinimide in the (2) is 3000-8000:100:2-6:4.5-15: 1.5-5.
Preferably, the temperature of the reaction in the step (2) is 45-75 ℃, and the reaction time is 6-18 h.
Preferably, the mass ratio of the ethyl acetate, the concentrated hydrochloric acid and the BOC-isoleucine-based polyamino acid in the step (3) is 7000-12000:1200-2000: 100.
Preferably, the mass ratio of the trifluoroacetic acid, the hydrobromic acid, the glacial acetic acid and the isoleucine-based polyamino acid in the step (4) is 1200-2000:5.5-8:4.5-7.5: 100.
Advantageous technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
the novel polypeptide compound is prepared by using the amino group of hexadecylamine as a polymerization site to initiate N6-carbobenzoxy-L-lysine cyclic internal anhydride to carry out polymerization reaction to prepare hexadecyl polyamino acid, wherein the terminal amino group of the hexadecyl polyamino acid is subjected to amidation reaction with BOC-L-isoleucine in a condensation system of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide to prepare BOC-isoleucine-based polyamino acid, further subjected to BOC removal treatment in an ethyl acetate and concentrated hydrochloric acid system to prepare isoleucine-based polyamino acid, and finally, in a system of trifluoroacetic acid, hydrobromic acid and glacial acetic acid, the carbobenzoxy structure in a molecular structure is hydrolyzed to generate amino to obtain the novel polypeptide compound, the prepared polypeptide compound has excellent antibacterial activity on bacteria and microorganisms such as salmonella through experimental tests of a bacteriostatic circle method, and the side chain of the novel polypeptide compound contains a hydrophobic long alkyl chain, so that the novel polypeptide compound has good hydrophobicity, can endow the polypeptide compound with excellent anticoagulant activity, and has wide application prospects in the fields of antibacterial materials, medical dressings and the like.
Drawings
FIG. 1 is a reaction scheme for preparing hexadecylpolyamino acids;
FIG. 2 is a reaction scheme for preparing a BOC-isoleucine-based polyamino acid;
FIG. 3 is a reaction formula for preparing an isoleucine-based polyamino acid;
FIG. 4 is a reaction scheme for preparing novel polypeptide compounds;
FIG. 5 is a schematic diagram of the bacteriostatic loop method.
Detailed Description
To achieve the above object, the present invention provides the following embodiments and examples: the synthesis method of the novel polypeptide compound is as follows:
(1) adding a mixed solvent of dichloromethane and N, N-dimethylformamide, N6-benzyloxycarbonyl-L-lysine cyclic lactam and hexadecylamine into a reaction container, wherein the mass ratio of the four is 3500-6000:800-1500:100:3-8, carrying out polymerization reaction for 24-72 h at 35-50 ℃ after stirring and dissolving, carrying out reduced pressure distillation after the reaction to remove the solvent, then adding distilled water, and placing the mixture into a dialysis bag for dialysis and purification to obtain the hexadecyl polyamino acid.
(2) Adding N, N-dimethylformamide, hexadecyl polyamino acid and BOC-L-isoleucine into a reaction container, stirring to dissolve, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCl) and N-hydroxysuccinimide (NHS) in a mass ratio of 3000-8000:100:2-6:4.5-15:1.5-5, heating to 45-75 ℃ for reaction for 6-18 h, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
(3) Adding ethyl acetate, concentrated hydrochloric acid and BOC-isoleucine-based polyamino acid into a reaction container according to the mass ratio of 7000, 12000:1200, 2000:100, stirring for 2-5 h at 15-30 ℃, performing BOC removal treatment, adding distilled water into the solution for extraction, taking an ethyl acetate organic phase, performing reduced pressure distillation, adding an ethanol solvent into a product, placing the product in a dialysis bag, and performing dialysis purification to obtain the isoleucine-based polyamino acid.
(4) Adding trifluoroacetic acid, hydrobromic acid and glacial acetic acid into a reaction vessel, then adding isoleucine-based polyamino acid with the mass ratio of 1200-2000:5.5-8:4.5-7.5:100, stirring and hydrolyzing at 15-30 ℃ for 8-20 h, adding distilled water for dilution after reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis purification to obtain the novel polypeptide compound.
Example 1
(1) Adding 18 mL of dichloromethane and 4 mL of N-dimethylformamide mixed solvent, 0.5 g of N6-benzyloxycarbonyl-L-lysine cyclic lactam and 0.015 g of hexadecylamine into a reaction vessel, stirring and dissolving, carrying out polymerization reaction at 35 ℃ for 24-72 h, carrying out reduced pressure distillation after the reaction to remove the solvent, adding distilled water, and placing in a dialysis bag for dialysis and purification to obtain the hexadecyl polyamino acid.
(2) Adding 30 mL of N, N-dimethylformamide, 1 g of hexadecyl polyamino acid and 0.02 g of BOC-L-isoleucine into a reaction container, stirring to dissolve, adding 0.045 g of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 0.015 g of N-hydroxysuccinimide, heating to 45 ℃ for reaction for 6 hours, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
(3) Adding 70 mL of ethyl acetate, 12 mL of 25% concentrated hydrochloric acid and 1 g of BOC-isoleucine-based polyamino acid into a reaction container, stirring for 2 hours at 15 ℃, removing BOC, adding distilled water into the solution for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, placing the product in a dialysis bag, and carrying out dialysis purification to obtain the isoleucine-based polyamino acid.
(4) Adding 25 mL of trifluoroacetic acid, 0.11 g of hydrobromic acid and 0.09 g of glacial acetic acid into a reaction vessel, then adding 2 g of isoleucine-based polyamino acid, stirring and hydrolyzing at 15 ℃ for 8 h, adding distilled water for dilution after the reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis and purification to obtain the novel polypeptide compound.
Example 2
(1) 22 mL of dichloromethane and 5 mL of N-dimethylformamide mixed solvent, 0.5 g of N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and 0.025 g of hexadecylamine are added into a reaction vessel, stirred and dissolved, then a polymerization reaction is carried out for 36 h at 35 ℃, after the reaction, the solvent is removed by reduced pressure distillation, then distilled water is added, and the mixture is placed into a dialysis bag for dialysis and purification, so that the hexadecyl polyamino acid is obtained.
(2) Adding 45 mL of N, N-dimethylformamide, 1 g of hexadecyl polyamino acid and 0.032 g of BOC-L-isoleucine into a reaction container, stirring to dissolve, adding 0.07 g of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 0.025 g of N-hydroxysuccinimide, heating to 45 ℃ for reacting for 18 h, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
(3) Adding 80 mL of ethyl acetate, 15 mL of 30% concentrated hydrochloric acid and 1 g of BOC-isoleucine-based polyamino acid into a reaction container, stirring for 2 hours at 30 ℃, removing BOC, adding distilled water into the solution for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, placing the product in a dialysis bag, and carrying out dialysis purification to obtain the isoleucine-based polyamino acid.
(4) Adding 40 mL of trifluoroacetic acid, 0.13g of hydrobromic acid and 0.12 g of glacial acetic acid into a reaction vessel, then adding 2 g of isoleucine-based polyamino acid, stirring and hydrolyzing at 15 ℃ for 20 h, adding distilled water for dilution after reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis and purification to obtain the novel polypeptide compound.
Example 3
(1) 26 mL of a mixed solvent of dichloromethane and 6 mLN, N-dimethylformamide, 0.5 g of N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and 0.032 g of hexadecylamine were added to a reaction vessel, stirred and dissolved, and then subjected to a polymerization reaction at 40 ℃ for 48 hours, after the reaction, the solvent was distilled off under reduced pressure, and then distilled water was added, and the mixture was dialyzed and purified in a dialysis bag to obtain hexadecylpolyamino acid.
(2) Adding 65 mL of N, N-dimethylformamide, 1 g of hexadecyl polyamino acid and 0.045 g of BOC-L-isoleucine into a reaction vessel, stirring to dissolve, adding 0.13g of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 0.04 g of N-hydroxysuccinimide, heating to 60 ℃ for reaction for 12 hours, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
(3) Adding 100 mL of ethyl acetate, 18 mL of 30% concentrated hydrochloric acid and 1 g of BOC-isoleucine-based polyamino acid into a reaction container, stirring for 4 hours at 20 ℃, removing BOC, adding distilled water into the solution for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, placing the product in a dialysis bag, and carrying out dialysis purification to obtain the isoleucine-based polyamino acid.
(4) Adding 35 mL of trifluoroacetic acid, 0.15 g of hydrobromic acid and 0.135 g of glacial acetic acid into a reaction vessel, then adding 2 g of isoleucine-based polyamino acid, stirring and hydrolyzing at 20 ℃ for 12 h, adding distilled water for dilution after the reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis and purification to obtain the novel polypeptide compound.
Example 4
(1) Adding 30 mL of dichloromethane and 7 mL of N-dimethylformamide mixed solvent, 0.5 g of N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and 0.04 g of hexadecylamine into a reaction vessel, stirring and dissolving, carrying out polymerization reaction at 50 ℃ for 72 h, carrying out reduced pressure distillation after the reaction to remove the solvent, adding distilled water, and placing in a dialysis bag for dialysis and purification to obtain the hexadecyl polyamino acid.
(2) Adding 80 mL of N, N-dimethylformamide, 1 g of hexadecyl polyamino acid and 0.06 g of BOC-L-isoleucine into a reaction container, stirring to dissolve, adding 0.15 g of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 0.05 g of N-hydroxysuccinimide, heating to 75 ℃ for reacting for 18 h, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
(3) Adding 120 mL of ethyl acetate, 20 mL of 35% concentrated hydrochloric acid and 1 g of BOC-isoleucine-based polyamino acid into a reaction container, stirring for 5 hours at 30 ℃, removing BOC, adding distilled water into the solution for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, placing the product in a dialysis bag, and carrying out dialysis purification to obtain the isoleucine-based polyamino acid.
(4) Adding 40 mL of trifluoroacetic acid, 0.16 g of hydrobromic acid and 0.15 g of glacial acetic acid into a reaction vessel, then adding 2 g of isoleucine-based polyamino acid, stirring and hydrolyzing at 30 ℃ for 20 h, adding distilled water for dilution after reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis and purification to obtain the novel polypeptide compound.
Comparative example 1
(1) Adding 25 mL of dichloromethane and 7 mL of N-dimethylformamide mixed solvent, 0.5 g of N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and 0.035 g of hexadecylamine into a reaction vessel, stirring and dissolving, carrying out polymerization reaction at 50 ℃ for 48 h, carrying out reduced pressure distillation after the reaction to remove the solvent, adding distilled water, and placing in a dialysis bag for dialysis and purification to obtain hexadecyl polyamino acid.
(2) Adding 30-80 mL of N, N-dimethylformamide, 1 g of hexadecyl polyamino acid and 0.04 g of BOC-L-isoleucine into a reaction container, stirring to dissolve, adding 0.08 g of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 0.025 g of N-hydroxysuccinimide, heating to 45 ℃ for reaction for 12 hours, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
Comparative example 2
(1) Adding 30 mL of dichloromethane and 7 mL of N-dimethylformamide mixed solvent, 0.5 g of N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and 0.035 g of hexadecylamine into a reaction vessel, stirring and dissolving, carrying out polymerization reaction at 35 ℃ for 72 h, carrying out reduced pressure distillation after the reaction to remove the solvent, adding distilled water, and placing in a dialysis bag for dialysis and purification to obtain hexadecyl polyamino acid.
(2) Adding 60 mL of N, N-dimethylformamide, 1 g of hexadecyl polyamino acid and 0.045 g of BOC-L-isoleucine into a reaction vessel, stirring to dissolve, adding 0.12 g of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 0.04 g of N-hydroxysuccinimide, heating to 55 ℃ for reaction for 6 hours, adding distilled water into the solution after the reaction, and dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid.
(3) Adding 100 mL of ethyl acetate, 20 mL of 35% concentrated hydrochloric acid and 1 g of BOC-isoleucine-based polyamino acid into a reaction container, stirring for 2 hours at 20 ℃, removing BOC, adding distilled water into the solution for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, placing the product in a dialysis bag, and carrying out dialysis purification to obtain the isoleucine-based polyamino acid.
The novel polypeptide compounds prepared in the examples and isoleucine-based polyamino acid prepared in comparative examples were prepared into 5 mg/mL polypeptide solutions, respectively, and the antibacterial activity was tested by plate-punching, and 2 mL of the polypeptide solutions with a concentration of 2X 10 was transferred6Adding the agar culture medium and the pH buffer solution into CFU/mL salmonella suspended bacteria solution, then dropwise adding 1 mL polypeptide solution, culturing for 24 h at 37 ℃ in a constant temperature incubator, and measuring the diameter mark antibacterial property of the antibacterial ring.
Claims (7)
1. A novel polypeptide compound characterized by: the synthesis method of the novel polypeptide compound is as follows:
(1) adding a mixed solvent of dichloromethane and N, N-dimethylformamide, N6-benzyloxycarbonyl-L-lysine cyclic internal anhydride and hexadecylamine into a reaction container, stirring and dissolving, carrying out polymerization reaction, carrying out reduced pressure distillation after the reaction to remove the solvent, adding distilled water, and placing into a dialysis bag for dialysis and purification to obtain hexadecyl polyamino acid with a structural formula of
；
(2) Adding N, N-dimethylformamide, hexadecyl polyamino acid and BOC-L-isoleucine into a reaction container, stirring and dissolving, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide, heating for reaction, adding distilled water into the solution after the reaction, dialyzing and purifying to obtain the BOC-isoleucine-based polyamino acid with the structural formula shown in the specification
；
(3) Adding ethyl acetate into a reaction container, dropwise adding concentrated hydrochloric acid and BOC-isoleucine-based polyamino acid, stirring at 15-30 ℃ for 2-5 h, removing BOC, extracting the solution with distilled water, taking an ethyl acetate organic phase, distilling under reduced pressure, adding an ethanol solvent into the product, placing the product into a dialysis bag, dialyzing and purifying to obtain the isoleucine-based polyamino acid with the structural formula shown in the specification
；
(4) Adding trifluoroacetic acid, hydrobromic acid and glacial acetic acid into a reaction vessel, then adding isoleucine-based polyamino acid, stirring and hydrolyzing at 15-30 ℃ for 8-20 h, adding distilled water for dilution after reaction, adding ethyl acetate for extraction, taking an ethyl acetate organic phase, carrying out reduced pressure distillation, adding an ethanol solvent into a product, and carrying out dialysis purification to obtain a novel polypeptide compound, wherein the structural formula is shown in the specification
。
2. The novel polypeptide compound of claim 1, characterized in that: the mass ratio of the dichloromethane, the N, N-dimethylformamide, the N6-benzyloxycarbonyl-L-lysine cyclic anhydride and the hexadecylamine in the step (1) is 3500-6000:800-1500:100: 3-8.
3. The novel polypeptide compound of claim 1, characterized in that: the temperature of the polymerization reaction in the step (1) is 35-50 ℃, and the reaction time is 24-72 h.
4. The novel polypeptide compound of claim 1, characterized in that: the mass ratio of the N, N-dimethylformamide, the hexadecyl polyamino acid, the BOC-L-isoleucine, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and the N-hydroxysuccinimide in the (2) is 3000-8000:100:2-6:4.5-15: 1.5-5.
5. The novel polypeptide compound of claim 1, characterized in that: the reaction temperature in the step (2) is 45-75 ℃, and the reaction time is 6-18 h.
6. The novel polypeptide compound of claim 1, characterized in that: the mass ratio of the ethyl acetate, the concentrated hydrochloric acid and the BOC-isoleucine-based polyamino acid in the step (3) is 7000-12000:1200-2000: 100.
7. The novel polypeptide compound of claim 1, characterized in that: the mass ratio of the trifluoroacetic acid, the hydrobromic acid, the glacial acetic acid and the isoleucine-based polyamino acid in the step (4) is 1200-2000:5.5-8:4.5-7.5: 100.
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| CN105694030A (en) * | 2016-04-05 | 2016-06-22 | 中国科学院化学研究所 | Oligo-polyamino acid and sodium alginate combined hybrid antibacterial hydrogel |
| CN106832260A (en) * | 2016-12-22 | 2017-06-13 | 苏州度博迈医疗科技有限公司 | A kind of degradable antibacterial polyaminoacid and preparation method thereof |
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| CN105694030A (en) * | 2016-04-05 | 2016-06-22 | 中国科学院化学研究所 | Oligo-polyamino acid and sodium alginate combined hybrid antibacterial hydrogel |
| CN106832260A (en) * | 2016-12-22 | 2017-06-13 | 苏州度博迈医疗科技有限公司 | A kind of degradable antibacterial polyaminoacid and preparation method thereof |
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Effective date of registration: 20230329 Address after: 518102 609, Building 37, Yintian Industrial Zone, Yantian Community, Xixiang Street, Bao'an District, Shenzhen City, Guangdong Province Patentee after: Shenzhen Leyishi Ecological Technology Co.,Ltd. Address before: 236500 No.46, wangxiaozhuang, Xiezhuang administrative village, Zhuanji Town, Jieshou City, Fuyang City, Anhui Province Patentee before: Wang Xuefei |
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