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Mycobacterium tuberculosis LAM oligosaccharide conjugate as well as preparation method and application thereof

A technology of Mycobacterium tuberculosis and conjugates, applied in chemical instruments and methods, carrier-bound antigen/hapten components, antibacterial drugs, etc., to achieve good immune effect, avoid bacterial drug resistance, and solve the effect of low immune protection

Active Publication Date: 2014-08-27
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the Mycobacterium tuberculosis complex oligosaccharide conjugate vaccine is prepared by using the arabinoid oligosaccharide containing the mannose fragment at the non-reducing end of Mycobacterium tuberculosis LAM as the hapten, and linking it with the carrier, and there is no relevant literature report yet.

Method used

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  • Mycobacterium tuberculosis LAM oligosaccharide conjugate as well as preparation method and application thereof
  • Mycobacterium tuberculosis LAM oligosaccharide conjugate as well as preparation method and application thereof
  • Mycobacterium tuberculosis LAM oligosaccharide conjugate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: general synthetic method

[0035] A: Glycosylation reaction

[0036] Take the glycosyl donor (1.2 equivalents), the glycosyl acceptor (1 equivalent) and the molecular sieve (equal to the weight of the donor) and dissolve them in dry anhydrous dichloromethane, and cool the reaction solution to - After stirring at 30°C for 30 minutes, N-iodosuccinimide (NIS, 1.2 equivalents) and a catalytic amount of silver trifluoromethanesulfonate (AgOTf) were added. The reaction solution was slowly raised to room temperature, neutralized with triethylamine after TLC detected that all the raw materials had reacted, filtered to remove insoluble solids, the filtrate was spin-dried, and the crude product was separated through a silica gel column to obtain the target product (the eluent used was petroleum ether (PE ) / ethyl acetate (EA), unless otherwise stated).

[0037] B: deacetylation reaction

[0038] Dissolve the raw materials in methanol, add 1mol / L sodium methoxide m...

Embodiment 2

[0046] Example 2: 3-aminopropyl α-D-mannosyl-(1→2)-α-D-mannosyl-(1→5)-β-D-arabinosyl-(1→2) -Synthesis of α-D-arabinose-KLH conjugate (A11-KLH)

[0047] (1) Synthesis of 5-O-tert-butyldimethylsilyl-D-arabinose (A1)

[0048]

[0049] Dissolve D-arabinose (5.00g, 33mmol) in 100mL of pyridine, add tert-butyldimethylsilyl chloride (6.00g, 40mmol) and a catalytic amount of 4-dimethylaminopyridine at 0°C, and dissolve the reaction solution Stir at room temperature for 6 hours. The reaction was tracked by TLC (EA). After all the raw materials were reacted, the solvent was evaporated to dryness to obtain a yellow viscous liquid. The crude product was separated by a silica gel column to obtain a colorless oily liquid (6.34 g, yield 72%).

[0050] (2) Synthesis of 1,2,3-tri-O-acetyl-5-O-tert-butyldimethylsilyl-α,β-D-arabinose (A2)

[0051]

[0052] Take A1 (5.00g, 19mmol) and dissolve it in a mixed solvent of 5mL acetic anhydride and 20mL pyridine, cool the mixed solution to 0°C...

Embodiment 3

[0083] Example 3: 3-aminopropyl α-D-mannosyl-(1→2)-α-D-mannosyl-(1→5)-β-D-arabinosyl-(1→2) -Synthesis of α-D-arabinose-BSA conjugate (A11-BSA)

[0084]

[0085] Take A11 (1 mg) and BSA (3 mg) to synthesize A11-BSA conjugate (2.7 mg) according to the general synthesis method E in Example 1. Mass Spectrum: MALDI-TOF MS (m / z): 74354

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Abstract

The invention relates to a mycobacterium tuberculosis LAM oligosaccharide conjugate as well as a preparation method and application thereof. A structural general formula of the mycobacterium tuberculosis LAM oligosaccharide conjugate is described in the specification. The invention also relates to application of the mycobacterium tuberculosis LAM oligosaccharide conjugate in preparation of a tuberculosis vaccine. In the mycobacterium tuberculosis LAM oligosaccharide conjugate, a chemical structure of oligosaccharide is definite and single, is not a mixture and can be synthesized by adopting a chemical method, the problem that immune protection force of a Bacilli Calmette Guerin vaccine is small can be solved, better immune effect can be produced to the crowd with low immunity, and the problem that bacterial drug resistance is produced as antibiotics are greatly used, can be solved.

Description

technical field [0001] The invention relates to a Mycobacterium tuberculosis LAM oligosaccharide conjugate and its preparation method and application, belonging to the technical field of tuberculosis vaccine development. Background technique [0002] Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis with a high mortality rate. Tuberculosis is mainly transmitted through the respiratory tract, and can also be transmitted through the digestive tract, skin and uterus. Most infected people usually do not have any symptoms. Only some infected people with low body immunity or increased cell-mediated allergy will develop the disease. If not treated in time, about half of the infected people will die. The incidence of this disease has increased year by year in recent years. The main reasons for this phenomenon are: (1) The abuse of antibiotics leads to the continuous enhancement of bacterial resistance; (2) Cross-infection with AIDS; (3) The poor basic medi...

Claims

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Application Information

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IPC IPC(8): C07K14/765C07K14/795A61K39/385A61K47/48A61P31/06
CPCA61K39/04A61K39/385A61K47/61A61K47/62C07K14/765C07K14/795
Inventor 郭忠武王利振顾国锋安莲
Owner SHANDONG UNIV
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