Preparation method of helicobacter pylori lipopolysaccharide outer-core octasaccharide

A Helicobacter pylori and octasaccharide technology, applied in the field of sugar chemistry, can solve problems such as poor repeatability of experiments, uneven molecular structure, and small amount of products

Active Publication Date: 2018-04-24
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the core structure of Helicobacter pylori lipopolysaccharide is mainly extracted from inactivated bacteria by biological methods. The disadvantages are ...

Method used

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  • Preparation method of helicobacter pylori lipopolysaccharide outer-core octasaccharide
  • Preparation method of helicobacter pylori lipopolysaccharide outer-core octasaccharide
  • Preparation method of helicobacter pylori lipopolysaccharide outer-core octasaccharide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of sugar block 8 as figure 1 :

[0041] Such as figure 1 As shown, using peracetylated glucose 1 as the starting material, boron trifluoride ether (BF 3 OEt 2 ) under the action of p-cresylthiol to generate all-acetylthioglucoside compound 2. Acetyl in sodium methoxide (NaOCH 3 ) under the action of deacetylation, exposing four hydroxyl groups. Tetrahydroxy compound and benzaldehyde dimethyl acetal (PhCH(OCH 3 ) 2 ) in p-toluenesulfonic acid (p-TsOHH 2 O) under the catalysis of generating 4,6-benzylidene protected thioglucoside 3 compounds. Selectively protect 3-OH with 2-methylnaphthalene (2-Nap) to obtain compound 4, and protect 2-OH with benzyl (Bn) to obtain compound 5. Using borane (BH 3 THF) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) selectively open the 4,6-benylidene group to expose 6-OH to obtain compound 6. The 6-OH of compound 6 was protected with benzoyl (Bz) to obtain fully protected glucoglucoside compound 7. The hydrol...

Embodiment 2

[0053] The synthesis of sugar block 21, the route is figure 2 .

[0054] Such as figure 2 As shown, using 2,3-O-propylidene-4-O-benzylmannothioside 9 as the starting material, the corresponding aldehyde compound 10 was obtained after swern oxidation. Then the carbon chain at the 6-position was extended by witting to obtain the deoxygenated olefin compound 11 at the 6-position. 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 joint action of dihydroxylation to obtain 6,7-di-hydroxyl compound 12. Using dibutyltin oxide (Bu 2 SnO) selectively protected compound 13 with Nap. 6-OH was protected with Bn to obtain compound 14. The compound 15 was obtained after removal of the propylidene group under the action of 80% acetic acid, and the 3-OH was selectively protected by Nap to obtain the heptose block 16. Compound 17 was obtained after the 2-OH of sugar block 16 was protected with Lev...

Embodiment 3

[0068] The synthesis of sugar block 28, the route is image 3 .

[0069] Such as image 3 As shown, starting from compound 22, 2-OH was protected with Bz to obtain compound 23. Compound 23 opened the propylidene group under the action of 80% acetic acid to obtain compound 24. The 3-OH of compound 24 was selectively protected with Bn to obtain compound 25. The 4-OH of compound 25 was protected with Lev to obtain compound 26. The sulfoglycoside 26 was hydrolyzed under NBS conditions, the terminal OH was exposed, and the terminal -OH was reacted with tert-butyldimethylsilyl chloride (TBSCl) to obtain galactose 27 with a fully protected terminal TBS. Lev was removed under the action of hydrazine acetate to obtain the galactose building block 28.

[0070] Specific test operation and steps:

[0071] Compound 23: Compound 22 (4.2 g, 11.8 mmol) was dissolved in pyridine (59.5 mL), and stirred at 0° C. for 5 min. BzCl (2.78 mL, 24 mmol) and a catalytic amount of DMAP were added....

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Abstract

The invention discloses a preparation method of helicobacter pylori lipopolysaccharide outer-core octasaccharide and belongs to the field of chemistry. Structure of the helicobacter pylori lipopolysaccharide outer-core octasaccharide is (alpha-D-Glc-(1-3)-alpha-D-Glc-(1-4)-beta-D-Gal-(1-7)-D-alpha-D-Hep[alpha-D-Glc-(1-6)-alpha-D-Glc-(1-6)-alpha-D-Glc-(1-2)-D-alpha-D-Hep]-Linker. The structure is composed of three kinds of monosaccharide including glucose, galactose and heptasaccharide, wherein the structure contains 5 glucose alpha glucosidic bonds, a galactose beta glucosidic bond and two heptasaccharide alpha glucosidic bonds. The octasaccharide is prepared by utilizing remote neighboring participation effect, solvent effect, temperature effect and synergism of additive and leaving group. A reducing end of the octasaccharide can be connected with a connection arm used for being connected with protein in the future to form glycoconjugate for immunology research.

Description

technical field [0001] The invention relates to a preparation method of the helicobacter pylori lipopolysaccharide outer core octasaccharide, belonging to the field of sugar chemistry. Background technique [0002] Helicobacter pylori (H.P.) was listed as a class I carcinogen by the World Health Organization in 1994. It is a Gram-negative bacterium that inhabits the surface of epithelial cells and is covered by mucus on the surface of gastric mucosa. More than 50% of the world's population is infected with Helicobacter pylori in the upper gastrointestinal tract, up to 70% in developing countries, and 20% to 30% in developed countries. In acute infection, 20% of patients develop ulcers, and 1% of patients may even develop gastric cancer or mucosa-associated lymphoma. The 2005 Nobel Prize in Physiology or Medicine was awarded to two Australian scientists, Warren and Mashall, for their discovery of the important role of Helicobacter pylori in causing digestive tract diseases a...

Claims

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Application Information

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IPC IPC(8): C08B37/00A61P31/04
CPCC08B37/006Y02P20/55
Inventor 尹健胡静彼特·泽贝格邹小鹏
Owner JIANGNAN UNIV
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