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Anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and preparation method thereof

A technology for methoxyphenol glycosides and compounds, which is applied in the field of oligosaccharide synthesis, can solve the problems of unclear antigen, uncertainty, complex composition and the like, and achieves the effects of simple synthesis route, good stereoselectivity and low cost of raw materials

Active Publication Date: 2017-04-19
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are many disadvantages in the existing anthrax vaccine, the main problems are: (1) the composition is complex and uncertain; (2) the antigen corresponding to the immune response is not clear enough, and the pertinence is poor; (3) the branched chain of the vaccine is difficult to control, and the effect Unstable; (4) Unsatisfactory immune effect

Method used

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  • Anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and preparation method thereof
  • Anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and preparation method thereof
  • Anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and preparation method thereof

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Embodiment 1

[0036] (1) Preparation of monosaccharide acceptor (6)

[0037] Commercially available glucosamine hydrochloride 1 (40 g, 186 mmol) and sodium bicarbonate (46.8 g, 558 mmol) were dissolved in 360 mL of distilled water. After the reaction was stirred at room temperature for 30 min, 2,2,2-trichloroethyl chloroformate (Troc-Cl, 30 mL, 233 mmol) was slowly added, and the reaction was continued to stir for 4 h. The solvent was removed by filtration and dried to give a pale yellow residue (54 g, 150 mmol). Dissolve in 200mL of pyridine, and slowly add acetic anhydride (88mL, 900mmol) dropwise in ice bath. The reaction solution was stirred overnight at room temperature. After TLC detected that the reaction was complete, 100 mL of methanol was added to quench the reaction. The solvent was pulled dry, extracted with 500 mL of ethyl acetate, and then washed with saturated sodium bicarbonate solution, 1M hydrochloric acid solution and saturated sodium chloride solution in sequence. Th...

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Abstract

The invention relates to an anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and a preparation method thereof. The structural formula of the trisaccharide 4-methoxyphenoside compound is shown in the description; and in the formula, R1 is an acetyl group, R2 is a benzyl group, R3 is an acetamido group, and the end position is a p-methylphenoxyl group. The compound can be used for preparing oligosaccharide-like conjugates, can be used for synthesis reaches of anthrax carbohydrate vaccines, has the advantages of concise synthesis route, simplicity in operation, low raw material cost, strong versatility, and good glycosylation reaction stereoselectivity, and is suitable for synthesizing various oligosaccharide compounds.

Description

technical field [0001] The invention relates to the technical field of oligosaccharide synthesis, in particular to 2,3,4,6-tetra-O-benzyl-β-D-galactosyl (α1→4)-(2,3,4,6-tetra- O-acetyl-β-D-galactopyranosyl)(β1→3)-2-deoxy-2-acetylamino-β-D-glucose p-methoxyphenol glycoside and its preparation method. Background technique [0002] The shell of most pathogenic pathogens is usually covered with a layer of polysaccharides with weak immunogenicity, which enables them to escape the immune surveillance of the host; Structural vaccines have made breakthroughs in the control of infectious diseases. Vaccines against neonatal pneumonia and meningitis have been launched, and vaccines against malaria, tumors, and various fungal and bacterial infections are under different research stage, showing good research prospects. [0003] Bacillus anthracis is the largest Gram-positive bacillus among pathogenic bacteria, which belongs to the genus of aerobic Bacillus, and its propagules are easy ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00
Inventor 俞世冲黄蕾李翔胡宏岗汪亭柴晓云邹燕赵庆杰刘超吴俊琪吴秋业
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY