Fucosylation chondroitin sulfate oligosaccharide and preparation method, compound and application thereof

A technology of fucosylation and sulfated cartilage, which is applied in the directions of esterification and saccharide, chemical instruments and methods, and drug combination, etc.

Active Publication Date: 2020-01-24
YANTAI DONGCHENG PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all current research results are based on oligosaccharides obtained by extraction or degradation methods, and their structures are microscopically heterogeneous, so it is impossible to draw definite conclusions and clear structure-activity relationships.

Method used

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  • Fucosylation chondroitin sulfate oligosaccharide and preparation method, compound and application thereof
  • Fucosylation chondroitin sulfate oligosaccharide and preparation method, compound and application thereof
  • Fucosylation chondroitin sulfate oligosaccharide and preparation method, compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Example 1: Synthesis of Chondroitin Glycans

[0097] Take 25g of commercially available chondroitin sulfate A sodium salt and place it in 2.5L of hydrochloric acid-methanol solution (0.5% acetyl chloride, v / v), stir at room temperature for 24 hours, remove the solvent by suction filtration, and place the obtained solid in 2.5L of the same concentration again hydrochloric acid-methanol solution. This operation was repeated for three times, and the finally obtained solid was dissolved in 750 mL of 0.1 M sodium hydroxide solution, and stirred at room temperature for 24 hours. Add IR-120 cation exchange resin to neutralize the solution to pH = 3.5, remove the resin by filtration, add appropriate amount of sodium hydroxide solid to adjust to pH = 8.0, concentrate until dry to obtain white syrup. Dissolve the syrup with a small amount of distilled water and slowly drop it into 2000 mL of vigorously stirred absolute ethanol to precipitate a white precipitate, collect the prec...

Embodiment 2

[0098] Example 2: (β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D-galactopyranosyl)-(1→4)- (β-D-glucopyranose)-(1→3)-2-deoxy-N-acetylamino-D-galactopyranose disodium salt, (β-D-glucopyranose) -(1→3)-(2-deoxy-N-acetylamino-β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→ 3)-(2-Deoxy-N-acetylamino-β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→3)-2 -Deoxy-N-acetylamino-D-galactopyranose trisodium salt and (β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D -galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D-pyranose Lactosyl)-(1→4)-(β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D-galactopyranosyl)- Synthesis of (1→4)-(β-D-glucopyranose)-(1→3)-2-deoxy-N-acetylamino-D-galactopyranose tetrasodium salt

[0099] Take 15.0 g of the chondroitin polysaccharide obtained in Example 1 and place it in 750 mL of 0.10 M sodium acetate-acetic acid buffer solution containing 0.15 M sodium chloride at pH = 5.00, and use a constant temperature ...

Embodiment 3

[0102] Example 3: Azide-[(β-D-glucopyranosyl)-(1→3)-(2-deoxy-2-N-acetylamino-β-D-galactopyranosyl)-( 1→4)-(β-D-glucopyranosyl)-(1→3)-(2-deoxy-2-N-acetylamino-β-D-galactopyranosyl)] disodium salt synthesis

[0103] Take (β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D-galactopyranosyl)-(1→4)-(β- D-glucopyranose)-(1→3)-2-deoxy-N-acetylamino-D-galactopyranose disodium salt (660mg, 0.81mmol), N-methylmorpholine (2.4mL , 24.0mmol), and sodium azide (3.0g, 46.0mmol) were dissolved in water (15mL), cooled to 0°C, and 2-chloro-1,3-dimethyl imidazoline chloride (1.4g, 8.4mmol ), stirred for 15 minutes, removed the ice bath, and naturally rose to room temperature to continue the reaction for 36 hours. After the reaction was completed, the solvent was concentrated to remove, Sephadex LH-20 was desalted, and freeze-dried to obtain a white solid (531 mg, 78%). R f =0.24 (n-butanol / water / ethanol / acetic acid=1 / 1 / 1 / 0.05); 1 HNMR (600MHz,D 2 O)δ4.75(1H,d,J=9.4Hz),4.54-4.50(3H,m),4....

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Abstract

The invention discloses fucosylation chondroitin sulfate oligosaccharide provided with a structure shown in J. The definition of a substituent group is shown in the description in detail. Besides, theinvention further discloses a preparation method of the fucosylation chondroitin sulfate oligosaccharide. According to the preparation method, chondroitin sulfate A salt is used as a raw material andis subjected to enzymolysis, protecting group operation and glycosylation sequentially, the oligosaccharide compound is synthesized, and the certainty of the structure enables the compound to be applied to the medicine field.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, more specifically, to a fucosylated chondroitin sulfate oligosaccharide, a preparation method, a composition, and an application of the compound. Background technique [0002] Fucosylated chondroitin sulfate is a kind of glycosaminoglycan extracted from sea cucumber. Its structure is based on chondroitin sulfate glycan, and at the same time, there is a fucose side chain connected to the 3-hydroxyl group of aldonic acid sugar. , and have sulfonate groups at different positions, thus forming trisaccharide repeating units (J.Biol.Chem.1988,263,18176). [0003] [0004] Fucosylated chondroitin sulfate has biological functions such as anticoagulation, anti-HIV, anti-inflammation, and wound repair (Mar.Drugs 2014, 12, 232). Compared with heparin drugs, the anticoagulant activity has a different pharmacological mechanism, which greatly reduces the risk of bleeding (P Natl Acad Sci USA, 2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C12P19/26C12P19/14A61K31/737A61P7/02
CPCC08B37/0069C12P19/26C12P19/14A61K31/737A61P7/02A61P29/00C07H13/08C07H11/00C12P19/04C08L5/08Y02P20/55C07H5/06
Inventor 李中军张肖刘慧颖姚望
Owner YANTAI DONGCHENG PHARMA GRP
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