6-oxadiazole/thiadiazole chitooligosaccharide derivative as well as preparation and application thereof

A technology of thiadiazole chitosan oligosaccharides and derivatives, which is applied in the field of novel 6-oxa/thiadiazole chitosan oligosaccharides derivatives and their preparation and application, can solve the problems that the activity cannot reach the level of direct application, etc. Achieve the effects of improving biocompatibility, improving inhibitory activity, and expanding application fields

Active Publication Date: 2019-12-20
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although chitosan oligosaccharide has good bactericidal activity, its activity has not yet reached the level of direct application.

Method used

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  • 6-oxadiazole/thiadiazole chitooligosaccharide derivative as well as preparation and application thereof
  • 6-oxadiazole/thiadiazole chitooligosaccharide derivative as well as preparation and application thereof
  • 6-oxadiazole/thiadiazole chitooligosaccharide derivative as well as preparation and application thereof

Examples

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preparation example Construction

[0040] The preparation method of the derivative of the present invention: dissolving chitosan oligosaccharide in 13.5% lye, stirring at 50-70°C for 1-2h, then dissolving chloroacetyl in isopropanol equivalent to one-fifth of the volume of lye , and then added to chitosan oligosaccharide lye, and continued to react for 4-6h. After the reaction, the pH of the reaction solution was adjusted to be neutral, dialyzed, and freeze-dried to obtain 6-carboxymethyl chitosan oligosaccharide.

[0041] Disperse 6-carboxymethylchitooligosaccharide in a mixture of dichloromethane and pyridine (V:V=3:1), add DCC and DMAP and stir at room temperature for 18-24h, then add methanol and continue the reaction at room temperature 4-6h. After the reaction is finished, filter, wash the filter cake with ethanol and DMF, and dry the filter cake at 50-60° C. to obtain 6-methyl acetate chitosan oligosaccharide.

[0042] Dissolve 6-methyl acetate chitooligosaccharide in 50% ethanol, then react with hydraz...

Embodiment 1

[0045] The preparation of embodiment 1 6-oxadiazole chitosan oligosaccharide:

[0046] Weigh 5g chitosan oligosaccharide and dissolve in 50ml lye (6.75gNaOH / 50mlH 2 (0), stirred at 50° C. for 1 h, weighed 5.4 g of chloroacetic acid and dissolved it in 10 ml of isopropanol, then added the solution dropwise to the above-mentioned chitosan oligosaccharide solution within 30 min, and continued the reaction for 4 h. After the reaction finished, adjust the reaction solution to neutrality with 1M hydrochloric acid, then use the dialysis bag of 1000 molecular weight for dialysis, freeze-drying subsequently, obtain 4.2g yellow solid 6-carboxymethyl chitosan oligosaccharide (see figure 2 ).

[0047] Weigh 4g 6-carboxymethylchitooligosaccharide, 2g dicyclohexylcarbodiimide and 0.2g 4-diaminopyridine and disperse in 40ml organic solvent (methylene chloride / pyridine=3:1), stir at room temperature After 6 hours, 4ml of methanol was slowly added dropwise to the reaction system, and the re...

Embodiment 2

[0051] The preparation of embodiment 2 6-thiadiazole chitosan oligosaccharides:

[0052] Weigh 5g chitosan oligosaccharide and dissolve in 50ml lye (6.75gNaOH / 50mlH 2 (0), stirred at 50° C. for 1 h, weighed 5.4 g of chloroacetic acid and dissolved it in 10 ml of isopropanol, then added the solution dropwise to the above-mentioned chitosan oligosaccharide solution within 30 min, and continued the reaction for 4 h. After the reaction, the reaction solution was adjusted to neutrality with 1M hydrochloric acid, then dialyzed with a 1000 molecular weight dialysis bag, and then freeze-dried to obtain 4.2 g of yellow solid 6-carboxymethyl chitosan oligosaccharide.

[0053] Weigh 4g 6-carboxymethylchitooligosaccharide, 2g dicyclohexylcarbodiimide and 0.2g 4-diaminopyridine and disperse in 40ml organic solvent (methylene chloride / pyridine=3:1), stir at room temperature After 6 hours, 4ml of methanol was slowly added dropwise to the reaction system, and the reaction was continued for 1...

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Abstract

The invention belongs to a marine chemical engineering technology, and particularly relates to a novel 6-oxadiazole/thiadiazole chitooligosaccharide derivative and a preparation and application thereof. The derivative is shown as a general formula I, and in the formula I, X is O or S and n is 2-10. The derivative disclosed by the invention has relatively good solubility, a novel structure and verystrong bacterium killing capability.

Description

technical field [0001] The invention belongs to marine chemical engineering technology, and specifically relates to a novel 6-oxa / thiadiazole chitosan oligosaccharide derivative and its preparation and application. Background technique [0002] Bacteria is the most numerous type of all living things, and it exists in human life. It presents two sides to human life, including bacteria that are beneficial to human survival and development, such as parasitic bacteria in the human intestinal tract. Provide nutrients such as vitamins and amino acids, and maintain the "ecological balance" of the intestinal environment; Bacillus subtilis, as a beneficial microorganism in the plant rhizosphere, can promote the growth of host plants by secreting hormones, various enzymes and antibacterial substances, and enhance The ability of plants to resist adversities such as disease resistance, drought resistance and saline alkali resistance. There are also bacteria that can damage human health...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00A61K31/7056A61P31/04A61P31/10
CPCC07H15/26C07H1/00A61P31/04A61P31/10
Inventor 李鹏程高堃秦玉坤邢荣娥刘松于华华陈晓琳李克成李荣锋
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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