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Beta-1, 4 type glucuronic acid/mannuronic acidstraight-chain hybrid oligosaccharide as well as preparation method and application thereof

A technology of mannuronic acid and glucuronic acid, which is applied in the field of pharmaceutical compounds, can solve problems such as difficult quality control, and achieve the effects of simple quality control, simple preparation method, and easy industrialization

Pending Publication Date: 2021-12-10
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, a series of glucuronic acid oligosaccharides were obtained by oxidizing natural polysaccharides such as starch and microcrystalline cellulose through the TEMPO system, and the two uronic acid oligosaccharides showed good protective effects on mouse hippocampal neuron cells under glucose and hypoxia conditions. , Another example is the selective oxidation of konjac glucomannan through the TEMPO system to obtain a glucuronic acid / mannuronic acid oligosaccharide, but the reducing ends of the above three types of oligosaccharides all have different degrees of ring opening, which is difficult to achieve when the process is enlarged. Moderate quality control has a certain degree of difficulty

Method used

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  • Beta-1, 4 type glucuronic acid/mannuronic acidstraight-chain hybrid oligosaccharide as well as preparation method and application thereof
  • Beta-1, 4 type glucuronic acid/mannuronic acidstraight-chain hybrid oligosaccharide as well as preparation method and application thereof
  • Beta-1, 4 type glucuronic acid/mannuronic acidstraight-chain hybrid oligosaccharide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation process of β-1,4 type glucuronic acid / mannuronic acid linear hybrid oligosaccharides:

[0051] Step 1: Weigh 1g konjac glucomannan, add 192mg 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl radical and 1360mg sodium chlorite successively, then add 200mL. .2 M sodium acetate / acetate buffer solution (pH 4.7), stir well.

[0052] Step 2: Add 4 mL of 5% sodium hypochlorite solution to the solution in step 1, carry out the oxidation reaction at 25°C, and add 5 mL of absolute ethanol after 48 hours to terminate the reaction.

[0053] Step 3: Place the sample obtained above in a 500Da dialysis bag and dialyze for 72 hours to remove salt, filter through a rapid filter membrane to remove insoluble matter, remove the clear liquid from the lower layer, concentrate by rotary evaporation, and freeze-dry to obtain a β-1,4-type glucosin Acid / mannuronic acid linear hybrid polysaccharide solid matter.

[0054] Step 4: Dissolve the above-mentioned polysaccharide in 100 mM ...

Embodiment 2

[0093] Preparation method of β-1,4 type glucuronic acid / mannuronic acid linear hybrid oligosaccharides:

[0094] Step 1: Weigh 10g konjac glucomannan, add 3840mg 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl radical and 2720mg sodium chlorite successively, then add 2000mL. .2M sodium acetate / acetic acid buffer solution (pH 4.7), stir well.

[0095] Step 2: Add 50 mL of 5% sodium hypochlorite solution to the solution in step 1 to carry out the oxidation reaction at 25° C. After 72 hours, add 30 mL of absolute ethanol to terminate the reaction.

[0096] Step 3: Place the sample obtained above in a 500Da dialysis bag and dialyze for 72 hours to remove salt, filter through a rapid filter membrane to remove insoluble matter, take the lower clear liquid, concentrate by rotary evaporation, and freeze-dry to obtain β-1,4-type glucuronic acid / Mannocuronic acid straight-chain hybrid polysaccharide solid matter.

[0097] Step 4: Dissolving the above-mentioned polysaccharide in 1M t...

Embodiment 3

[0101] A preparation method of β-1,4 type glucuronic acid / mannuronic acid linear hybrid oligosaccharides:

[0102] Step 1: Weigh 2g konjac glucomannan, add 192mg 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl radical and 1360mg sodium chlorite successively, then add 200mL. .2 M sodium acetate / acetate buffer solution (pH 4.7), stir well.

[0103] Step 2: Add 12 mL of 5% sodium hypochlorite solution to the solution in step 1 to carry out the oxidation reaction at 25° C. After 96 hours, add 10 mL of absolute ethanol to terminate the reaction.

[0104] Step 3: Place the sample obtained above in a 500Da dialysis bag and dialyze for 72 hours to remove salt, filter through a rapid filter membrane to remove insoluble matter, take the lower clear liquid, concentrate by rotary evaporation, and freeze-dry to obtain β-1,4-type glucuronic acid / Mannocuronic acid straight-chain hybrid polysaccharide solid matter.

[0105] Step 4: Dissolve the above-mentioned polysaccharides in 100mM tri...

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Abstract

The invention discloses beta-1, 4 type glucuronic acid / mannuronic acid straight-chain hybrid oligosaccharide. The beta-1, 4 type glucuronic acid / mannuronic acid straight-chain hybrid oligosaccharide has the following general formula structure that the hybrid oligosaccharide has the advantages of low molecular weight, good water solubility, high bioavailability, easiness in quality control and the like, and has remarkable activity for treating ischemic brain diseases. The preparation process comprises the following steps of weighing konjac glucomannan, sequentially adding 4-acetamido-2, 2, 6, 6-tetramethylpiperidine-1-oxygen free radicals, sodium chlorite and an acidic buffer solution, and uniformly stirring, adding a sodium hypochlorite solution to oxidize, and adding an organic reagent to terminate the reaction to obtain the beta-1, 4 type glucuronic acid / mannuronic acid straight-chain hybrid polysaccharide; and hydrolyzing the hybrid polysaccharide, desalting, and freeze-drying to obtain the straight-chain hybrid oligosaccharide. The method has the advantages of mild reaction conditions, simple synthesis process, high yield, easily available preparation raw materials, low cost and easiness in industrialization.

Description

technical field [0001] The invention belongs to the technical field of medical compounds, and in particular relates to β-1,4 type glucuronic acid / mannuronic acid straight-chain hybrid oligosaccharides and a preparation method and application thereof. Background technique [0002] In recent years, with the improvement of people's living standards and the increase of aging, the morbidity and mortality of cardiovascular and cerebrovascular diseases are on the rise. Among various brain diseases, ischemic stroke accounts for the main part. Currently, it is used clinically Drugs used to prevent and treat ischemic stroke include aspirin and tissue plasminogen activator tPA. Aspirin prevents further formation of thrombus by preventing platelet aggregation. Although aspirin is widely used in the world at present, the effect of aspirin on acute stroke is not satisfactory. Tissue plasminogen activator tPA can dissolve thrombus, dredge blood vessels and reduce brain damage, but because...

Claims

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Application Information

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IPC IPC(8): C07H7/033C07H1/00A61P25/00A61P7/06C08B37/00
CPCC07H7/033C07H1/00A61P25/00A61P7/06C08B37/009
Inventor 张真庆吴芳霞李笃信易琳欧阳艺兰
Owner SUZHOU UNIV
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