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Process for sulphofication of mucopolysaccharide with galactosamine hexose aldehydic acid disaccharide based structure

A technology of uronic acid disaccharide and galactosamine, which is applied in the field of biomedicine, can solve the problems of harsh reaction conditions and complicated processes, and achieves the effects of good product stability and simple method.

Inactive Publication Date: 2007-07-18
NANJING KING FRIEND BIOCHEM PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Some of the above-mentioned methods are complicated in technology, and some of them require harsh reaction conditions.

Method used

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  • Process for sulphofication of mucopolysaccharide with galactosamine hexose aldehydic acid disaccharide based structure
  • Process for sulphofication of mucopolysaccharide with galactosamine hexose aldehydic acid disaccharide based structure
  • Process for sulphofication of mucopolysaccharide with galactosamine hexose aldehydic acid disaccharide based structure

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Experimental program
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Effect test

Embodiment 1

[0043] Embodiment 1 Preparation of dermatan sulfate sulfonated product

[0044] 1. Purification

[0045] Dermatan sulfate crude product 20g (optical rotation: -28.75 degrees), dissolved in 180ml water, adjusted to PH2.5, added 0.8gNaNO 2 , stir, and maintain the pH of the reaction solution at 1.5 to 4.5 by adding HCl or NaOH dropwise, test the solution with starch potassium iodide test paper, observe the color of the test paper, until the test paper does not turn blue, the reaction is complete; adjust the pH to 6.5, add ethanol to The volume content reached 41.2%. Over night, the precipitate was collected, dehydrated with ethanol, and dried. The weight loss on drying was 2.5%, and 11.7 g of dermatan sulfate with a purity of 99.0% was obtained. The measured optical rotation was -60.25 degrees.

[0046] 2. Sulfonation

[0047] Dermatan sulfate 10g (optical rotation: -60.25 degrees, loss on drying 2.5%), add 60ml of formamide, fully dissolve, stir, add 3.5ml of chlorosulfonic a...

Embodiment 2

[0050] Embodiment 2 Preparation of chondroitin sulfate sulfonated product

[0051] 1. Purification

[0052] 30g of crude chondroitin sulfate (optical rotation: -25.0 degrees), dissolved in 375ml of water, adjusted to pH 8.7, heated the solution to 76°C, added 1.2g of potassium permanganate to oxidize, reacted to the end, filtered, adjusted to pH 7.0 of the filtrate , adding 1.5 times the solution volume of ethanol for precipitation, overnight, collecting the precipitate, dehydrating with ethanol, drying, the weight loss on drying was 2.8%, and 19.7g of chondroitin sulfate with a purity of 92.0% was obtained, and the measured optical rotation was -29.25 degrees.

[0053] 2. Sulfonation

[0054] Add 10g of chondroitin sulfate (optical rotation: -29.25 degrees, loss on drying 2.8%), add 60ml of formamide, fully dissolve, stir, add 3.0ml of chlorosulfonic acid, react for 30 minutes, and precipitate with ethanol twice the volume of the solution. After 4 hours, discard the superna...

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Abstract

The present invention relates to process of sulfonating mucopolysaccharide with the basic galactosamine-hexuronic disaccharide structure to prepare sulfonated mucopolysaccharide product with antithrombogenic function. The process adopts chondrotin sulfate A and / or chondrotin sulfate or C or dermatan sulfate as material, and includes the steps of purifying material, dissolving in formamide, sulfonating with chlorosulfonic acid, separating sulfonated mucopolysaccharide precipitate in alcohol, mixing the water solution with the precipitate with strong alkaline anionic resin, adsorbing at pH5.0-7.5 for a night, washing with solution of sodium chloride, eluting in resin to collect eluted solution, precipitating with alcohol, dewatering with alcohol, and drying to obtain sulfonated mucopolysaccharide product. The process is simple, high in product stability and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for producing mucopolysaccharide side chain hydroxyl sulfonation containing a basic structure of galactosamine-hexuronic acid disaccharide, and belongs to the field of biomedicine. Background technique [0002] Mucopolysaccharides are nitrogen-containing sulfonated polysaccharides, which are the main components of connective tissue in cells and widely exist in the cells of various organs of mammals. Important mucopolysaccharides such as heparin, dermatan sulfate, heparan sulfate, chondroitin sulfate and hyaluronic acid are chain polysaccharides formed by repeated links of different disaccharide units. Polysulfonic acid-based mucopolysaccharides are valued for their functions of inhibiting blood coagulation, inhibiting thrombus formation, accelerating thrombus dissolution, hindering protein decomposition, and increasing blood flow. In recent years, the research on the sulfonation of mucopolysaccharides has become a hot...

Claims

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Application Information

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IPC IPC(8): C08B37/00A61K31/715
Inventor 唐明龙吴桂萍
Owner NANJING KING FRIEND BIOCHEM PHARMA CO LTD
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