Beta-1,2-D-oligomeric mannoprotein conjugates and preparation method and application thereof

A technology of mannoproteins and conjugates, which is applied in the field of β-1,2-D-oligomannose protein conjugates and its preparation, can solve problems such as limited immune response, achieve strong application value, and prevent leukemia. Effects of candida infection

Inactive Publication Date: 2017-02-22
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented preparation was tested on mouse cells infected with Candidiasis bacterium (a type called Candida Albis). It showed that this new formulation could stimulate powerful humoral responses against these germs without causing harm or even killing them themselves.

Problems solved by technology

This patents discusses how effective treatments against yeast infections involve administering specific substances called beta 1-2 mannanase enzyme from Cryptomeria macrogloba into patients who were previously exposed during their lifetime due to candlebite wounds. These agents help fight off harmful germs like this one causing these diseases through production of anti-microbial peptidogylurans (PGNG). However, there may be some limitations associated with current methods used to create PGNG vaccination protocols.

Method used

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  • Beta-1,2-D-oligomeric mannoprotein conjugates and preparation method and application thereof
  • Beta-1,2-D-oligomeric mannoprotein conjugates and preparation method and application thereof
  • Beta-1,2-D-oligomeric mannoprotein conjugates and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The synthesis of embodiment 1 compound 5

[0057] Monosaccharide acceptor 3 (1.23g, 2.5mmol) (J.Org.Chem.2001, 66, 8411.), donor 4 (1.95g, 3.0mmol) (J.Carbohydr.Chem.1994, 13, 421.) and activated Molecular sieves (1.0 g) were placed in a 100 mL round bottom flask and dried under vacuum for half an hour, then the mixture was dissolved in 50 mL of anhydrous dichloromethane. The suspension was stirred at room temperature under argon protection for half an hour, then cooled to -40°C, and then trimethylsilyl triflate (35.0 μL, 0.18 mmol) was slowly added dropwise. After half an hour, the reaction solution was neutralized and quenched with triethylamine and filtered with diatomaceous earth. After concentration, the initial product obtained was subjected to silica gel column chromatography (n-hexane / ethyl acetate, 12:1, v / v) to obtain a white foamy solid (2.23g, 92.4%).

[0058] 1 HNMR (400MHz, CDCl 3 )δ7.40-7.19(m,30H,Ar),5.88(m,1H,OCH 2 C H =CH 2 ),5.37(m,1H,OCH 2 ...

Embodiment 2

[0059] The synthesis of embodiment 2 compound 6

[0060] Compound 5 (1.85g, 2.0mmol) was dissolved in 100mL of anhydrous methanol, sodium methoxide (11.0mg, 0.2mmol) was added and stirred at room temperature overnight, after the reaction was completed, it was added to ion exchange resin IR 120 (H+form) And, the resin was removed by filtration, and the initial product obtained after concentration was subjected to silica gel column chromatography (n-hexane / ethyl acetate, 4:1, v / v) to obtain a white foamy solid (1.74g, 94.2%).

[0061] 1 H NMR (400MHz, CDCl 3 )δ7.55-7.23(m,30H,Ar),6.05-5.93(m,1H,OCH 2 C H =CH 2 ),5.40(m,1H,OCH 2 CH=C H 2 ),5.29(m,1H,OCH 2 CH=C H 2 ), 5.17 (dd, J=11.2Hz, 1H, OCH 2 Ph),5.05-4.93(m,4H,OCH 2 Ph), 4.90 (d, J=11.2Hz, 1H, OCH 2 Ph), 4.81(d, J=7.6Hz, 1H, H-1'), 4.72(d, J=12.0Hz, 1H, OCH 2 Ph),4.67-4.46(m,10H,OCH 2 Ph,O CH 2 CH=CH 2 ,H-1), 4.36(d,J=3.2Hz,1H,H-2),4.17-4.10(m,1H,O CH 2 CH=CH 2 ),4.01(t,J=9.6Hz,1H,H-4),3.88-3.71(m,6H,H...

Embodiment 3

[0062] The synthesis of embodiment 3 compound 7

[0063] Compound 6 (1.38 g, 1.5 mmol) was placed in a 100 mL round bottom flask, and then dimethyl sulfoxide (22.0 mL) and acetic anhydride (11.0 mL) were added. The reaction solution was stirred at room temperature for 18 hours, extracted with ethyl acetate, washed with saturated sodium carbonate and brine respectively, then dried with anhydrous sodium sulfate, filtered and concentrated to obtain the initial product, which was spun twice with toluene. The residue was dissolved in 40 mL of anhydrous tetrahydrofuran and cooled to -78°C, and L-Selectride (1 M THF, 7.5mL) and stirred for fifteen minutes, then removed the cooling device and placed at room temperature to continue stirring for fifteen minutes, quenched the reaction with methanol and diluted with 50mL dichloromethane, and the solutions were diluted with hydrogen peroxide solution (5%, 30mL), sodium hydroxide solution (1 M , 30mL), sodium thiosulfate solution (5%, 30m...

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Abstract

The invention discloses beta-1,2-D-oligomeric mannoprotein conjugates shown in the formula I in the description and a preparation method and application thereof. In the formula, n is 0 or 1 or 2, and R is carrier protein KLH or HSA. According to the preparation method, phosphorylated beta-1,2-D-oligomeric mannan oligosaccharides are synthesized with alpha-D-glucose as the raw material and then are coupled with the carrier protein, and the mannoprotein conjugates are obtained. When the prepared compounds are used for immunizing mice as an anti-candida albicans vaccine, the result shows that the compounds can induce the body to make a strong immune response; the beta-1,2-D-manninotriose protein conjugate has the highest immunogenicity, generated immune serum can be used for specifically recognizing candida albicans cell surface antigens, and thus the purpose of preventing candida albicans infection can be achieved. The beta-1,2-D-oligomeric mannoprotein conjugates have high application value.

Description

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Claims

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Application Information

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Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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