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Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

A technology of Helicobacter pylori and compounds, applied in the direction of carrier binding antigen/hapten components, sugar derivatives, sugar derivatives, etc., can solve problems such as research interference, few products, and insufficient specificity of lipopolysaccharide structure

Active Publication Date: 2019-05-21
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, the research on lipopolysaccharide of Helicobacter pylori is mainly extracted from inactivated bacteria. The disadvantage of this method is that the product obtained by one extraction is very small. In addition, due to the characteristics of bacterial gene expression and modification, the extracted lipopolysaccharide also exists The structure is not specific enough, and it is easy to have the characteristics of structure similar to impurities, the experiment repeatability is poor, and there is a certain interference to the research

Method used

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  • Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound
  • Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound
  • Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Synthesis of Sugar Block 5 as figure 1 :

[0089] Such as figure 1 As shown, the commercially available diacetone glucose 1 was used as the starting material to react with benzyl bromide under the action of sodium cyanide to generate 3-OBn glucose compound 2. After removing the propylidene group in 80% acetic acid solution, under the action of pyridine and acetic anhydride, the four newly formed hydroxyl groups were protected with acetyl groups to obtain compound 3. Then compound 3 was reacted in boron trifluoride ether (BF 3 ·Et 2 O) under the effect of reacting with thiophenol to generate 1-glucoside compound 4. Remove the three acetyl groups of compound 4 with methanolic sodium methoxide solution, then use benzaldehyde dimethyl acetal and p-toluene cyclic acid to protect the 4 and 6 hydroxyl groups, leaving the 2 Exposure of hydroxyl groups yields sugar building block 5.

[0090] Specific test operations and steps.

[0091] Compound 2: Dissolve diacetone gluco...

Embodiment 2

[0098] Synthesis of Sugar Block 8

[0099] The synthesis of sugar block 8 as figure 2

[0100] Such as figure 2 As shown, compound 8 is an analog of compound 5 with an amino linker assembled at the reducing end. Starting from compound 5, first protect 2-OH with acetyl to obtain compound 6, and then use p-methylphenylthio as a leaving group to react with the five-carbon amino linking arm under the accelerator NIS and TMSOTf to obtain compound 7. Finally, 2-OAc of compound 7 was removed with methanol and sodium methoxide to obtain sugar block 8.

[0101] Specific test operation and steps:

[0102] Compound 6: Compound 5 (9.7g, 21mmol) was dissolved in dry pyridine (60ml), and acetic anhydride (40ml) was slowly added in ice bath. The reaction solution was stirred at room temperature for 6 h. After the reaction of the raw materials was detected by TLC, the reaction solution was diluted with dichloromethane, washed with 1M hydrochloric acid solution, extracted with saturated...

Embodiment 3

[0106] Synthesis of Sugar Block 15

[0107] Such as image 3 As shown, the diacetone glucose 1 is used as the starting material, and the 3-allyl compound 9 is obtained by reacting with allyl bromide under the action of NaH. Compound 9 undergoes a ring-opening reaction in allyl alcohol added with hydrochloric acid to obtain 1,3-diallyl compound 10. Next, the remaining three exposed hydroxyl groups of glucose were protected with benzyl groups to obtain compound 11. Compound 11 uses palladium chloride in dry methanol to remove allyl groups at positions 1 and 3 exclusively to obtain 1-OH compound 12. The two hydroxyl groups formed in the previous step were protected with acetyl to obtain compound 13. Selective removal of the 1-OAc group under the action of hydrazine acetate gave 1-OH compound 14. Finally, compound 14 was reacted with trichloroacetonitrile and DBU to obtain trichloroacetimide ester glycosyl building block 15.

[0108] Specific test operation and steps:

[010...

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Abstract

The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tetraco-saccharide are obtained through chemical synthesis. A chemical synthesis method quite beneficial for generation of glucose alpha glucoside bonds is developed through a protective agent strategy, a temperature effect, a solvent effect and an additive effect, and used for synthesizing the helicobacter-pylorus O2 serotype O-antigen oligosaccharide compound assembled with aminolinks; glycoconjugate can be made of the synthesized helicobacter-pylorus O2 serotype O-antigen oligosaccharide compound assembled with the aminolinks and carrier protein for immunological researching, and an important role is played in the development of prevention and treatment of helicobacter pylori.

Description

technical field [0001] The invention relates to the synthesis of a helicobacter pylori O2 serotype O antigen oligosaccharide compound, which belongs to the field of organic synthesis. Background technique [0002] Helicobacter pylori is a microaerophilic Gram-negative bacterium that infects about half of the world's population. One proportion is even more as high as 80%. It is reported that 47% and 66% of the population in my country's urban and rural areas are infected with Helicobacter pylori. Oral-oral transmission and fecal-oral transmission are the main modes of transmission of the pathogen, and mother-to-child transmission is also one of the transmission modes of the pathogen. [0003] Most Helicobacter pylori infections occur in childhood, and once infected, the pathogenic bacteria may exist on the gastric mucosa for a lifetime. Although 70% of infected persons are clinically asymptomatic, this pathogen has been confirmed to be related to a series of gastrointestinal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H15/18C07H1/00C08B37/00A61P31/04A61K39/106A61K39/385
CPCA61K39/385A61P31/04C07H1/00C07H15/18C07H15/203C08B37/00A61K31/702Y02A50/30A61K45/06
Inventor 尹健胡静刘中华秦春君
Owner JIANGNAN UNIV
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