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Chemical synthesis method of plesiomonas shigelloides O51 serotype O-antigen oligosaccharide

A kind of technology of necromonas and serotypes, applied in the field of chemistry, can solve the problem of unreported chemical synthesis and so on

Active Publication Date: 2018-09-21
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, heteromodified polyaminosaccharide structures represented by P. shigella-like O51 polysaccharides are still considered as extremely challenging target molecules by synthetic chemists.
At present, the chemical synthesis of similar heteromodified polyaminosaccharide structures including P. shigella-like O51 polysaccharide has not been reported

Method used

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  • Chemical synthesis method of plesiomonas shigelloides O51 serotype O-antigen oligosaccharide
  • Chemical synthesis method of plesiomonas shigelloides O51 serotype O-antigen oligosaccharide
  • Chemical synthesis method of plesiomonas shigelloides O51 serotype O-antigen oligosaccharide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] Synthesis of allyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetylamino-α-D-glucopyranose (1*)

[0132] The reaction equation is as Figure 20 shown;

[0133] Under argon protection, 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetylamino-β-D-glucopyranose (M. Virlouvet et al., Adv.Synth .Catal.2010,352,2657-2662) (27g, 0.055mol) was dissolved in anhydrous dichloromethane (130mL), and activated Molecular sieves and allyl alcohol (18.7 mL, 0.274 mol). After cooling to -5°C, boron trifluoride diethyl ether (70 mL, 0.548 mol) was added dropwise. The reaction solution was stirred at 0° C. for 30 min, and then raised to room temperature for 71 hours. After the reaction, the reaction solution was poured onto 200 g of crushed ice, and the organic phase obtained after filtration with diatomaceous earth was extracted with water, saturated sodium bicarbonate solution, and saturated saline respectively, and the obtained organic phase was concentrated after dehydration by sodium su...

Embodiment 2

[0135] Synthesis of Allyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetylamino-α-D-glucopyranose (2*)

[0136] The reaction equation is as Figure 20 shown;

[0137] Compound 1* (50 g, 0.102 mol) was dissolved in methanol (800 mL), added with sodium methoxide (2.8 g, 0.051 mol) and stirred at room temperature for 5 hours. After the reaction, the reaction solution was neutralized with Amberlite IR 120 cation exchange resin, filtered and concentrated to obtain a white solid which was the target 3,4,6-trihydroxy sugar (37.1 g, 0.102 mol, quant.).

[0138] Trihydroxy sugar (71 g, 0.195 mol) was further dissolved in 300 mL of anhydrous DMF, benzaldehyde dimethyl acetal (35 mL, 0.234 mol) and p-toluenesulfonic acid (4.45 g, 0.023 mol) were added. After the reaction solution was reacted at 60°C for 24 hours, use a rotary evaporator to distill off the methanol generated in the reaction under reduced pressure, and continue to react at 60°C. This operation was repeated. After the reaction...

Embodiment 3

[0140] Synthesis of Allyl 4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-2-trichloroacetamido-2-deoxy-α-D-glucopyranose (3*)

[0141] The reaction equation is as Figure 20 shown;

[0142] Compound 2* (53.1g, 0.117mol) was dissolved in anhydrous dichloromethane / pyridine mixture (660mL, 7:1, v / v), and after cooling down to -20°C, trifluoro A solution of methanesulfonic anhydride (40 mL, 0.234 mol) in dichloromethane (150 mL) was gradually warmed to 10°C over 2 hours. After the reaction, the reaction solution was diluted with dichloromethane, and extracted with 1M HCl solution, saturated sodium bicarbonate, water and saturated brine in sequence. The organic phase was dehydrated by anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure at low temperature. The obtained crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate, 5:1 to 2:1, v / v) to obtain yellow syrup Product 3* (66.5g, 0.114mol, 98%). [α] D 20 =...

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Abstract

The invention discloses a chemical synthesis method of plesiomonas shigelloides O51 serotype O-antigen oligosaccharide, and belongs to the field of chemistry. According to the chemical synthesis method, D-glucose with rich resources is adopted, L-fucose and D-glucosamine and the like serve as raw materials to prepare three kinds of glycosylation building blocks, a synthetic route composed of eleven reaction modules is designed, and the preparation of a target oligosaccharide chain is completed successfully through the optimization of a protecting group and the optimization of the introductiontiming of a modified group. Raw materials of the prepared oligosaccharide chain is cheap and obtained easily, the preparation method is simple and repeated easily, and the oligosaccharide chain has agood application prospect in the development of novel drugs and vaccines of plesiomonas shigelloides and the like.

Description

technical field [0001] The invention relates to a method for chemically synthesizing oligosaccharides of Pseudomonas shigella-like O51 serotype O antigen, in particular to a heteromodified polyamino oligosaccharide in which amino linking arms are assembled at the reducing end, and belongs to the field of chemistry. Background technique [0002] Plesiomonas shigelloides, an active Gram-negative pathogen discovered in 1947, is the leading cause of severe diarrhea among international travelers. In addition, P. shigellai can cause a range of serious extraintestinal infections, especially in children and adults with underlying medical conditions, including sepsis and meningitis caused by P. shigellai infection It has a very high lethality rate (I. Stock, Rev. Med. Microbiol. 2004, 15, 129-139). At present, the treatment for this pathogenic bacterial infection relies on antibiotic therapy, and the continuous emergence of drug resistance reports in clinical treatment makes the tre...

Claims

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Application Information

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IPC IPC(8): C07H13/04C07H15/18C07H15/04C07H1/00
CPCC07H1/00C07H13/04C07H15/04C07H15/18C07H3/08A61P31/00Y02P20/55
Inventor 尹健胡静彼特·泽贝格秦春君
Owner JIANGNAN UNIV
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