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Synthetic method and intermediate compound of chondroitin sulfate tetrasaccharide

A technology of chondroitin sulfate and synthesis method, which is applied in the field of chemistry and can solve the problems of many synthesis steps, low yield, long route, etc.

Inactive Publication Date: 2019-08-06
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such a strategy has many synthetic steps and a long route, and the yield of the whole route is low due to the glycosylation operation involved.
At present, the synthesis of chondroitin sulfate tetrasaccharide alone requires about 23 steps of reaction, and the yield is less than 1%.

Method used

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  • Synthetic method and intermediate compound of chondroitin sulfate tetrasaccharide
  • Synthetic method and intermediate compound of chondroitin sulfate tetrasaccharide
  • Synthetic method and intermediate compound of chondroitin sulfate tetrasaccharide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131]Example 1: (β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D-glucopyranosyl)-(1→4)-( Synthesis of β-D-glucopyranosyl)-(1→3)-2-deoxy-N-acetylamino-D-glucopyranose disodium salt

[0132] Take 51.0 g of hyaluronic acid dry powder (molecular weight of about 500,000) and place it in 2500 mL of 0.10 M sodium acetate-acetic acid buffer solution containing 0.15 M sodium chloride at pH = 5.00. Swelling (about 72h) is a colorless, uniform viscous colloidal liquid. The temperature of the jelly liquid was raised to 37.0° C. in a constant temperature water bath, and 1.0 g of hyaluronidase dry powder (purchased from Sigma-Aldrich Company, product number H-3506, Lot # SLBL1922V) was added at this time, and stirred at 37.0° C. for two weeks. After the reaction, the reaction solution was heated to boiling, and stirred at 105°C for 15 minutes. After the solution was no longer turbid, it was quickly cooled to room temperature, mixed with 1 / 20 volume of absolute ethanol, distilled unde...

Embodiment 2

[0133] Example 2: (2,3,4-tri-O-acetyl-β-D-glucopyranosyl-methyl)-(1→3)-(4,6-di-O-acetyl- 2-Deoxy-N-acetylamino-β-D-glucopyranosyl)-(1→4)-(2,3-di-O-acetyl-β-D-glucopyranosyl) -Synthesis of -(1→3)-1,4,6-tri-O-acetyl-2-deoxy-N-acetylamino-D-glucopyranose

[0134] (β-D-glucopyranosyl)-(1→3)-(2-deoxy-N-acetylamino-β-D-glucopyranosyl)-(1→4)-(β-D -Glucopyranosyl)-(1→3)-2-deoxy-N-acetylamino-D-glucopyranose disodium salt crude product 96.0g was dissolved in 12L, 0.08M freshly refrigerated methanolic hydrogen chloride solution. Then the reaction solution was left standing at 4°C for 96h. After the reaction, the reaction solution was neutralized to neutral with triethylamine, then distilled under reduced pressure, and concentrated to dryness. Add 405 mL of pyridine, cool to 0° C., slowly dropwise add 230 mL of acetic anhydride, and slowly raise the reaction solution to room temperature, and stir at room temperature for 24 h. After the reaction was completed, the reaction liquid was ...

Embodiment 3

[0138] Example 3: (2,3,4-tri-O-acetyl-β-D-glucopyranosyl-methyl)-(1→3)-(4,6-di-O-acetyl- 2-Deoxy-N-acetylamino-β-D-glucopyranosyl)-(1→4)-(2,3-di-O-acetyl-β-D-glucopyranosyl) Synthesis of -(1→3)-4,6-di-O-acetyl-2-deoxy-N-acetylamino-D-glucopyranose

[0139] Take (2,3,4-tri-O-acetyl-β-D-glucuronomethyl)-(1→3)-(4,6-di-O-acetyl-2-deoxy-N -Acetylamino-β-D-glucopyranose)-(1→4)-(2,3-di-O-acetyl-β-D-glucuronyl)-(1→3)-1 , 30.2g (24.6mmol) of 4,6-tri-O-acetyl-2-deoxy-N-acetylamino-D-glucopyranose was dissolved in 240mL tetrahydrofuran, and 15.5mL (90.7mmol) was slowly added dropwise under stirring 3-N,N-dimethyl-aminopropylamine, and stirred at room temperature for 3h. Dilute the reaction solution with 650 mL of chloroform, wash the organic phase three times with 150 mL of 1M hydrochloric acid solution, extract the aqueous phase three times with 150 mL of chloroform, combine the organic phases, wash once with 230 mL saturated aqueous sodium bicarbonate solution, and wash once with sa...

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Abstract

The invention discloses a method for synthesis of chondroitin sulfate tetrasaccharide. The method comprises that orderly through enzymatic hydrolysis, protecting group protection, protecting group conversion, selective deprotection, hydroxyl oxidation and selective reduction, an intermediate compound shown in the formula O is prepared from hyaluronate as a starting material, and chondroitin sulfate tetrasaccharide is prepared from the intermediate compound shown in the formula O, wherein substituents in the formula O are specifically defined in the specification. The invention provides the intermediate compound for synthesis of chondroitin sulfate tetrasaccharide. Compared with the existing synthesis method, the method provided by the invention has the advantages of simple synthesis route, no glycosylation reaction, high reaction yield and good application prospect.

Description

technical field [0001] The application belongs to the technical field of chemistry, and more specifically, relates to a synthesis method of chondroitin sulfate tetrasaccharide and an intermediate compound thereof. Background technique [0002] Chondroitin sulfate is a glycosaminoglycan that exists widely in the body. Its structure is composed of glucuronic acid and N-acetylgalactosamine. In its structure, the hydroxyl group can be sulfated to varying degrees, so it is called chondroitin sulfate. . Chondroitin sulfate is covalently combined with proteins in the extracellular matrix to form proteoglycans, which are widely distributed in the intercellular space and are very important glycosaminoglycans. Chondroitin sulfate participates in many extremely important biochemical processes in the body, such as: participating in cell-cell interaction, inhibiting the regeneration of nerve axons, affecting the proliferation and metastasis of cancer cells, and combining with many extra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H11/00C07H15/04C07H9/06C07H9/02C07H1/00C12P19/26C12P19/14
CPCY02P20/55
Inventor 李中军姚望沙勐张肖孟祥豹李树春李庆
Owner PEKING UNIV
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