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6-amine-substituted-6-deoxidizing chitosan derivant and preparation method thereof

A technology of deoxychitosan and derivatives, applied in the field of marine chemical engineering, can solve the problems of poor solubility, limited use, weak bacteriostatic activity, etc., and achieve good solubility, enhanced bacteriostatic effect, and strong regional selectivity. Effect

Active Publication Date: 2012-07-11
海臻(上海)生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chitosan has a certain inhibitory effect on bacteria, fungi, etc. under acidic conditions, but due to its poor solubility under neutral pH conditions and its own weak antibacterial activity, it is directly used as an antibacterial agent. limited use
There is no report about 6-amine substituted-6-deoxy chitosan derivatives

Method used

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  • 6-amine-substituted-6-deoxidizing chitosan derivant and preparation method thereof
  • 6-amine-substituted-6-deoxidizing chitosan derivant and preparation method thereof
  • 6-amine-substituted-6-deoxidizing chitosan derivant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0028] Preparation method of derivatives: chitosan in dimethylformamide (DMF) and phthalic anhydride to protect the 2-position NH 2 Under the premise of carrying out 6-position bromination reaction, the reaction temperature is 100-130 ℃, and the reaction time is 5-10 hours; after the reaction, the product is poured into ice water, filtered, and dried after washing the filter cake with sufficient water and ethanol, Obtained N-phthaloyl chitosan. The mass-volume ratio of chitosan and DMF is 1:20-100, and the reaction molar ratio of chitosan and phthalic anhydride is 1:3-5. The above N-phthaloyl chitosan derivatives were dispersed in N-methylpyrrolidone (NMP), and N-bromosuccinimide (NBS) and triphenylene were added in an ice-water bath and under nitrogen protection. Phosphine (TPP), followed by reaction at 50-100°C for 1-4 hours. The obtained product was precipitated with ethanol, the supernatant was discarded by centrifugation, washed repeatedly with ethanol, and finally drie...

Embodiment 1

[0034] Preparation of Example 1 Derivative 1

[0035]Put 1.0 g of 6-bromo-6-deoxy-N-phthaloyl chitosan and 26 ml of ethylenediamine into a three-necked flask, react at 80°C for 24 hours, pour the reactant into 50 ml of isopropanol, and the resulting precipitate Repeated washing with ethanol, centrifugation and freeze-drying to obtain an intermediate. Take 0.5g of the intermediate and add it to the three-necked flask, then add 25ml of NMP and 25ml of hydrazine hydrate, and react at 100°C for 4 hours. The reaction product is precipitated with ethanol, washed repeatedly by centrifugation, and freeze-dried to obtain derivative 1. The structural formula is shown in Table 1.

[0036] The infrared spectrum shows that: the infrared spectrum of chitosan derivative 1 ( image 3 ) and the infrared spectra of chitosan ( figure 1 ), the N-H stretching vibration peak of the primary amine group is broadened, making 2889.92cm -1 The C-H stretching vibration peak at 1583.70cm becomes the sh...

Embodiment 2

[0037] Example 2 Preparation of Derivative 2

[0038] Put 1.0 g of 6-bromo-6-deoxy-N-phthaloyl chitosan, 26 ml of diethylenetriamine, and 10 ml of distilled water into a three-necked flask, react at 80°C for 48 hours, and pour the reactant into 50 ml of isopropanol , the obtained precipitate was repeatedly washed with ethanol, centrifuged and freeze-dried to obtain an intermediate. Take 0.5g of the intermediate and add it to the three-necked flask, then add 25ml of NMP and 25ml of hydrazine hydrate, and react at 100° C. for 4 hours. The reaction product is precipitated with ethanol, washed repeatedly by centrifugation, and freeze-dried to obtain derivative 2. The structural formula is shown in Table 1.

[0039] The infrared spectrum shows: the infrared spectrum of chitosan derivative 2 ( Figure 4 ) and the infrared spectra of chitosan ( figure 1 ) compared to 3425.93 and 2872.43cm -1 The signal of N-H stretching vibration peak and hydrocarbon stretching vibration peak of p...

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Abstract

The invention belongs to the technology of ocean chemical engineering, in particular to a 6-amine-substituted-6-deoxidizing chitosan derivant and a preparation method thereof. As shown in the general formula I, an amino compound can be introduced at the 6 position of chitosan, so that the derivant is strong in area selectivity. By introducing toxic or non-toxic amino-compounds on the chitosan, remarkable effects for improving anti-bacteria effect of the chitosan can be achieved, and the production using process of the derivant is led to be low in toxicity and environment-friendly. The formula I is shown in the description, wherein m=0-20; and n=4-4000.

Description

technical field [0001] The invention belongs to marine chemical engineering technology, in particular to a novel 6-amine substituted-6-deoxychitosan derivative and a preparation method thereof. Background technique [0002] With the development of society, the market has an increasing demand for antibacterial drugs, including veterinary drugs and feed additives, pesticides, antibacterial materials, and food preservatives. Antibiotics are widely used due to their low cost, large yield and good antibacterial effect. However, the abuse of antibiotics leads to the generation of drug-resistant microorganisms, and causes drug residues to pollute the environment and endanger human health. Therefore, the development of new green antibacterial drugs has become a research hotspot at home and abroad. [0003] Chitosan, also known as chitosan, is the product of deacetylation of chitin, and its chemical name is poly(1,4 glycoside)-2-amino-β-D-glucose. It widely exists in the shells of...

Claims

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Application Information

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IPC IPC(8): C08B37/08
Inventor 李鹏程孟祥涛邢荣娥刘松于华华秦玉坤李克成崔金会李荣锋李冰
Owner 海臻(上海)生物科技有限公司
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