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Method for synthesizing heptasaccharide of lentinan core fragment beta-(1-> 6) branched chain beta-(1-> 3) main chain

A technology of core fragments and lentinan, applied in chemical instruments and methods, drug combinations, sugar derivatives, etc., can solve the problem of normal cell killing, etc., and achieve the effect of extremely simple route, high yield and convenient operation

Active Publication Date: 2022-07-12
艾立斯特(合肥)生物科技有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

Cyclophosphamide at 70 mg / kg inhibited 59% of U14 tumors, but a large number of normal cells were killed

Method used

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  • Method for synthesizing heptasaccharide of lentinan core fragment beta-(1-> 6) branched chain beta-(1-> 3) main chain
  • Method for synthesizing heptasaccharide of lentinan core fragment beta-(1-> 6) branched chain beta-(1-> 3) main chain
  • Method for synthesizing heptasaccharide of lentinan core fragment beta-(1-> 6) branched chain beta-(1-> 3) main chain

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Experimental program
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Embodiment 1

[0039] Preparation of Tetrasaccharide Acceptor 7 and Trisaccharide Donor 9

[0040] (1) 2,3,4,6-Tetra-O-acetylglucose trichloroacetimidate 1 (2.96 g, 6 mmol) was dissolved in 10 mL of dichloromethane to give solution A, 1,2- 5,6-Di-O-isopropylidene glucose 2 (1.56 g, 6 mmol) was dissolved in 10 mL of dichloromethane to give solution B, A and B were mixed to give solution C, to C was added TMSOTf (28 μL, 0.25 mmol), stirred at 25°C, and after 2-4 hours of reaction, thin layer chromatography analysis indicated that the reaction was complete. The solvent was evaporated under reduced pressure, and the disaccharide 3 was obtained by coupling. Disaccharide 3 (3.54 g, 5.4 mmol) was dissolved in 20 ml of alkanolamine-dichloromethane, stirred at 25° C. After 8-10 hours of reaction, thin-layer chromatography analysis indicated that the reaction was completed, and the solvent was evaporated under reduced pressure to obtain Disaccharide 4 in 94.1% yield.

[0041] (2) 2,3,4,6-Tetra-O-ac...

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Abstract

The invention relates to a synthesis method of heptasaccharide of a lentinan core fragment beta-(1-> 6) branched chain beta-(1-> 3) main chain, which has biological activity and can be particularly used as an antitumor drug. The preparation method comprises the following steps: firstly, preparing a 1-3 connected disaccharide receptor, taking 2, 3, 4, 6-tetra-O-acetyl glucose trichloroacetimidate and 2, 4, 6-tri-O-acetyl-tetra-O-benzyl glucose trichloroacetimidate as glycosyl donors, coupling to obtain tetrasaccharide under the action of lewis acid, removing benzyl, taking the tetrasaccharide as a tetrasaccharide receptor, taking 2, 3, 4, 6-tetra-O-acetyl glucose trichloroacetimidate as a glycosyl receptor, taking 2, 3, 4, 6-tetra-O-acetyl glucose trichloroacetimidate as a glycosyl receptor, and taking 2, 3, 4, 6-tetra-O-acetyl glucose trichloroacetimidate as a glycosyl receptor. The preparation method comprises the following steps: by taking 1, 2, 3, 4, 6-tetra-O-acetylglucose trichloroacetimidate as a glycosyl donor and phenylthioglucose as a glycosyl receptor, coupling under the action of lewis acid to obtain a trisaccharide donor, coupling the trisaccharide donor and the tetrasaccharide receptor under the action of lewis acid to obtain heptasaccharide, and removing all protecting groups to obtain the beta-(1-> 6) branched chain beta-(1-> 3) main chain shiitake heptasaccharide.

Description

technical field [0001] The present invention relates to a method for synthesizing heptasaccharide of β-(1→6) branched β-(1→3) main chain of lentinan core fragment which has biological activity, especially can be used as an antitumor drug. Background technique [0002] Modern research has shown that many fungal polysaccharides have anti-tumor effects, such as Ganoderma lucidum polysaccharides, lentinan, and Grifola polysaccharides. Further research found that the anti-tumor activity of polysaccharides is mainly through the body's immune system rather than directly inhibiting the growth of tumor cells, so polysaccharide anti-tumor drugs are much less toxic and side effects to the human body than other anti-tumor drugs. A common structural feature of these biologically active polysaccharides is an oligodextran containing a β-(1→6) branched β-(1→3) backbone. These polysaccharides are mostly derived from the lentinan lentinan of Lentinus edodes (shiitake mushroom). However, lik...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/00C07H13/04C07H15/203C07H1/00A61P35/00
CPCC08B37/0024C07H13/04C07H15/203C07H1/00A61P35/00Y02P20/55
Inventor 朱玉亮袁婷婷
Owner 艾立斯特(合肥)生物科技有限公司
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