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Synthesizing method for helicobacter pylori O:6 serotype O-antigen sugar chains

A technology of Helicobacter pylori and serotypes, applied in the field of carbohydrate chemistry, can solve problems such as constraints, insufficient specificity of lipopolysaccharide structure, and research interference.

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

[0007] At present, the research on the lipopolysaccharide of Helicobacter pylori is all extracted from inactivated bacteria. The structure is not specific enough, and it is easy to have the characteristics of similar structure to impurities. The repeatability of the experiment is poor, and there is a certain interference to the research.
However, in the process of complex sugar chemical synthesis, the construction of glycosidic bonds is the most basic but also the most difficult and critical issue in sugar synthesis. Different from organic compounds, the methodology of sugar synthesis is still immature and incomplete. It is considered to be the only one in the field of organic chemistry that has many methods (dozens of them) but there is no universal method for everyone. recognized field
Due to the complex structure of the sugar module and the low selectivity of the cis-glycosidic bond, it is difficult to realize the construction of the structure, thus restricting the research on the chemical synthesis method of O:6 serotype O-antigen oligosaccharides

Method used

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  • Synthesizing method for helicobacter pylori O:6 serotype O-antigen sugar chains
  • Synthesizing method for helicobacter pylori O:6 serotype O-antigen sugar chains
  • Synthesizing method for helicobacter pylori O:6 serotype O-antigen sugar chains

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Synthesis of Example 1 Sugar Block 8*:

[0087] Synthetic route such as image 3 shown.

[0088] Using 2,3-O-propylidene-4-O-benzylmannothioside as the starting material, after swern oxidation, the 6-position hydroxyl was oxidized to aldehyde to obtain compound 1*. Then, the carbon chain at the 6-position was extended by wittig reaction to obtain the 6-position deoxygenated alkene compound 2*. Olefin compounds in potassium osmate (K 2 OSo 4 ), potassium ferricyanate (K 3 Fe(CN) 6 ) and potassium carbonate (K 2 CO 3 ) under the combined action of dihydroxylation to obtain 6,7-di-hydroxyl compound 3*. Bn protection of 6,7-di-hydroxyl under the action of sodium hydride (NaH) gave compound 4*. After removing the propylidene group under the action of 80% acetic acid, the compound 5* was obtained, and then under the action of D(+)-10-camphorsulfonic acid (CSA), the 2,3-position hydroxyl group was ring-formed and protected. The ring was opened under weak acid conditi...

Embodiment 2

[0098] Synthesis of Example 2 Sugar Block 13*:

[0099] Synthetic route such as Figure 4 shown.

[0100] Such as figure 2 , starting from compound 3*, using dibutyltin oxide (Bu 2 SnO) selective 7-OH Bn protection to obtain compound 9*, and then 6-OH protection with Lev to obtain compound 10*. After removing the propylidene group of compound 10* under the action of 80% acetic acid, the 2,3-OH was protected with acetyl group to obtain the sugar block 11*.

[0101] The synthesis of sugar building blocks 13*, firstly, using the previously prepared intermediate compound 3,4-position starting materials, in dibutyltin oxide (Bu 2 Under the action of SnO), the 3-OH of compound 5* was selectively protected by Bn to obtain compound 12*, and finally the 2-OH was protected by acetyl to obtain the heptose block 13*.

[0102] Specific test operation and steps:

[0103] Compound 9*: Compound 3* (0.77g, 2mmol) and Bu 2 SnO (0.75g, 3mmol) was dissolved in dry toluene (10mL), and the ...

Embodiment 3

[0108] The synthesis of embodiment 3 reducing end trisaccharides:

[0109] The synthetic route of the reducing end trisaccharide is as follows Figure 5 shown.

[0110] 3.1 pair Figure 5 The conditions of the glycosylation reaction in the trisaccharides at the reducing end were optimized (Table 1), and the conditions for determining the optimal glycosylation reaction were as follows: the glycosyl donor and the acceptor were co-distilled three times in toluene; adding anhydrous DCM , the reaction concentration is 0.1M, the activated or Molecular sieves; after the mixture was cooled to -10°C and stirred for 15 minutes, the activation reagents TMSOTf (0.12eq) and NIS (1.2eq) were added, and the reaction time was 3h. After the reaction, triethylamine (Et 3 N) terminate the reaction. The reaction solution was filtered, diluted with DCM and then diluted with saturated NaHCO 3 Wash, anhydrous Na 2 SO 4 After drying and concentration, it was separated and purified by silic...

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Abstract

The invention discloses a synthesizing method for helicobacter pylori O:6 serotype O-antigen sugar chains, and belongs to the field of sugar chemistry. According to the synthesizing method, aminolinkis assembled at the reduction tail ends of the helicobacter pylori O:6 serotype O-antigen sugar chains, and synthetic oligosaccharide chains can be coupled with carrier molecules or can be immobilizedon corresponding substrates. D-glucosamine, D-galactose, D-mannose and L-fucose which are low in cost and easy to obtain are used as starting materials, and through a series of chemical reactions, seven glycosylated blocks are obtained; then the sugar blocks are used, and under the effect of a corresponding activating reagent, through a series of glycosidation reactions, the multiple helicobacterpylori O:6 serotype O-antigen sugar chains are obtained through coupling. The oligosaccharide chains prepared with the method, the raw materials are low in cost and easy to obtain, the preparing method is simple and easy to repeat, and the oligosaccharide chains have good application prospects in the aspects such as novel drugs and vaccine development of helicobacter pylori.

Description

technical field [0001] The invention specifically relates to a method for synthesizing sugar chains of Helicobacter pylori O:6 serotype O-antigen, belonging to the field of sugar chemistry. Background technique [0002] Since Warren.Marshall first isolated Helicobacter pylori (Hp) from the stomach of gastritis patients in 1983, scholars from various countries have found that Hp is related to chronic active gastritis, gastroduodenal ulcer, and gastric mucosa through extensive and in-depth research. In 1994, the International Center for Cancer Research classified it as a class I carcinogen. As a Gram-negative bacterium, Hp is a group of slender, flexible, spiral-shaped, free-moving prokaryotic microorganisms, its characteristics are between bacteria and protozoa, mainly located in the deep layer of human gastric mucosa, Gastric mucosal epithelial cells are mostly in gastric pits, epithelial folds and glandular lumens. About 50% of the world's population is infected with Heli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00A61P31/04A61P1/04C08B37/00C07K2/00
CPCA61P1/04A61P31/04C07H1/00C07H15/18C07K2/00C07H15/04A61K39/105A61K2039/6031C08B37/006A61K39/385C08B37/00
Inventor 尹健胡静田光宗
Owner JIANGNAN UNIV
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