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Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide

A Pseudomonas aeruginosa, synthesis method technology, applied in the field of chemical synthesis of Pseudomonas aeruginosa O11 serotype O antigen oligosaccharides, to achieve the effect of simple and efficient method

Active Publication Date: 2019-04-16
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention develops a method for synthesizing D-fucosamine from D-glucose, and successfully solves the stereoselection of building 1,2-α-cis-glycosidic bonds through the synergistic effect of solvent effect, temperature effect and additive effect sexual problems

Method used

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  • Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide
  • Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide
  • Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The synthesis of sugar building block 3 (D-glucose building block) is as follows figure 1 :

[0049] like figure 1 shown, starting with peracetylglucose 1, in dry N,N-dimethylformamide using hydrazine acetate (NH 2 -NH 2 -AcOH) selectively hydrolyzes the acetyl group at position 1. The resulting 1-OH glucose 2 was then purified in anhydrous dichloromethane using trichloroacetonitrile (Cl 3 CN) and 1,8-diazabicycloundec-7-ene (DBU) to give glucosyl trichloroacetimide ester 3.

[0050] Specific test operations and steps:

[0051] Compound 2: Peracetylglucose 1 (5.0 g, 12.8 mmol) was dissolved in dry DMF (65 ml), and hydrazine acetate (1.45 g, 15.6 mmol) was added. The reaction was stirred at 40°C for 6 h, and the disappearance of the reaction was monitored by TLC. The reaction solution was cooled to room temperature, washed with saturated NaCI solution, separated organic phase, washed with anhydrous NaCI 2 SO 4 It was dried, concentrated and purified by silica ge...

Embodiment 2

[0054] The synthetic route of sugar building block 7 (L-fucose building block) is figure 2 .

[0055] like figure 2 As shown, using allyl 2-deoxy-2 azido-L-fucoside 4 as the starting material, firstly removing the acetyl groups at positions 3 and 4 in an alkaline environment containing sodium methoxide, the obtained Under the action of dibutyltin oxide and bromomethylnaphthalene, the dihydroxy compound is selectively protected with Nap group at the 4th position to obtain compound 5, and the hydroxyl group of 3-Nap compound 5 is protected with benzyl group to generate compound 6. Finally, the Nap group of 6 was removed with DDQ to obtain compound 3-OH compound 7.

[0056] Specific test operations and steps:

[0057] Compound 5: Allyl 2-deoxy-2azido-L-fucoside 4 (500 mg, 2.2 mmol) Anhydrous toluene (22 ml) followed by addition of dibutyltin oxide (814 mg, 3.3 mmol). The reaction solution was heated to 110 °C and stirred for 1 h. Subsequently, the reaction solution was coo...

Embodiment 3

[0062] The synthetic route of sugar block 17 is image 3 .

[0063] like image 3 As shown, starting from 3,4,6-O-triacetylmannosene 8, and iodobenzene diacetate (PhI(OAc) 2 ), azidotrimethylsilane (TMS-N 3 ) and diphenyldiselenide (Ph 2 Se 2 ) addition reaction to obtain 1-selenophenyl-2-azido compound 9. The three acetyl groups of 9 were removed with methanol and sodium methoxide, and then the hydroxyl group at position 6 was selectively protected with 4-toluenesulfonyl chloride (TsCl) to obtain compound 10. Next, the Ts group of 6-Ts glucose 10 was iodized with sodium iodide, followed by sodium cyanoborohydride (NaCNBH 3 ) to reduce the 6th position to a methyl group to obtain D-fucose compound 11. With p-methoxybenzyl chloride (PMBCl) and dibutyltin oxide (Bu 2 SnO) selectively protects the 3-position of the D-fucose compound to obtain compound 12, and then protects the 4-position hydroxyl with a benzyl group to obtain compound 13. The 4-position Nap of 13 is remov...

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Abstract

The invention discloses a chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide, and belongs to the field of chemistry. The method comprises the steps that a D-glucose block, an L-fucosamine block and a D-fucosimide block are utilized to construct O antigen trisaccharide, wherein the D-glucose block or the L-fucosamine block is connected with the D-fucosimide block through a 1,2-alpha-cis-glycosidic bond, the D-glucose block is connected with the L-fucososamine block through a 1,2-alpha-trans-glycosidic bond, and the 1,2-alpha-cis-glycosidic bond is constructed in a mixed solvent; the mixed solvent comprises two or more of dichloromethane, diethyl ether and thiophene. The method has the advantages that D-mannose is utilized as a raw material to obtain D-fucose simply, conveniently and efficiently; the uniform construction of the cis-glycosidic bond is achieved by relying on the appropriate mixed solvent; the stereoselectivity can reach 100%; and the method has a good application prospect in the development of novel drugs and vaccines for resisting Bacillus pyocyaneus and the like.

Description

technical field [0001] The present invention relates to a chemical synthesis method of Pseudomonas aeruginosa O11 serotype O antigen oligosaccharide, and belongs to the field of chemistry. Background technique [0002] Pseudomonas aeruginosa is a class of aerobic, rod-shaped, Gram-negative bacteria that generally inhabit soil and water environments. In particular, Pseudomonas aeruginosa is also a class of opportunistic pathogens that are widely present in hospital environments, causing bacteremia, urinary tract infections, and pneumonia. Susceptible populations for Pseudomonas aeruginosa include burn patients, patients in the ICU, post-surgery patients, and patients with immune system deficiencies such as cancer, diabetes, and congenital vesicular fibrosis. Epidemiological studies of Pseudomonas aeruginosa in ventilator-associated pneumonia (VAP) and hospital-acquired pneumonia (HAP) in mainland my country found that in VAP, Pseudomonas aeruginosa accounted for 19.4% of all...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00C07K2/00A61P31/04
CPCA61P31/04C07H1/00C07H15/04C07K2/00A61K39/00A61K31/738C07H3/06A61K39/104
Inventor 尹健胡静刘中华秦春君
Owner JIANGNAN UNIV
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