Cronobacter thuringiensis type 5 lipopolysaccharide O-antigen oligosaccharide fragment and preparation method and application thereof

A technology of Cronobacter and lipopolysaccharide, which is applied to the preparation of sugar derivatives, antigen carriers, chemical instruments and methods, etc., can solve problems such as inhomogeneity, and achieve the effects of reasonable design, good purity, and simple separation

Pending Publication Date: 2022-02-25
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently used glycoconjugate vaccines are polysaccharides extracted from bacterial

Method used

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  • Cronobacter thuringiensis type 5 lipopolysaccharide O-antigen oligosaccharide fragment and preparation method and application thereof
  • Cronobacter thuringiensis type 5 lipopolysaccharide O-antigen oligosaccharide fragment and preparation method and application thereof
  • Cronobacter thuringiensis type 5 lipopolysaccharide O-antigen oligosaccharide fragment and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1: 2-Amino-1-ethyl α-D-glucopyranosyl-(1→2)-[2-nitrogen-acetyl-β-D-glucopyranosyl-(1→3) Preparation of -]-β-L-rhamnopyranosyl-(1→4)-2-nitro-acetyl-β-D-glucopyranoside (CT-1)

[0077] The synthetic route of CT-1, the O-antigen oligosaccharide fragment of Cronobacter zurich type 5 lipopolysaccharide, is as follows:

[0078]

[0079] Reagents and reaction conditions in the above-mentioned synthetic route:

[0080] (a) NIS, TfOH, 1,2-dichloroethane, -30°C, 81%, α:β=1:3;

[0081] (b) Cu(OAc) 2 ,CH 2 Cl 2 ,CH 3 OH, r.t., 88%;

[0082] (c) TfOH,CH 2 Cl 2 ,-78℃, 55%;

[0083] (d) NIS, Ir Complex, THF, H2O, r.t., 78%;

[0084] (e) NIS, TfOH, -100℃, CH 2 Cl 2 ,Et 2 O, 70%, only α;

[0085] (f)i.N 2 h 4 ,CH 3 CH 2 OH,reflux; ii.Ac 2 O, pyridine, r.t.; iii. CH 3 ONa,CH 3 OH,CH 2 Cl 2 , r.t.; vi. Pd(OH) 2 ,H 2 O,CH 3 OH,CH 2 Cl 2 .

[0086] (1) p-tolyl 4-oxo-benzyl-2-oxo-allyl-3-oxo-pyridinecarbonyl-1-thio-α-L-rhamnopyranoside (1)

[0087]Dis...

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Abstract

The invention relates to a cronobacter thelingiensis type 5 lipopolysaccharide O-antigen oligosaccharide fragment and a preparation method and application thereof. The prepared oligosaccharide fragment is a cronobacter thelingiensis type 5 lipopolysaccharide O-antigen tetrasaccharide repeating unit and is prepared by taking various protected monosaccharide modules as raw materials and carrying out glycosylation reaction through a sequential glycosylation strategy, the C-1 site of a pyranosyl group at the reducing end of the oligosaccharide fragment is modified by an amino alkane chain, and can be conjugated with proteins, lipids, polypeptides and the like to prepare oligosaccharide conjugates, and then related immunological research is carried out. The preparation method disclosed by the invention is reasonable in design, strong in operability, simple in separation, high in product yield and good in purity. Immunological research is carried out by synthesizing polysaccharide repeated fragments with different reducing ends, and the method has important significance on research and development of corresponding cronobacter carbohydrate vaccines.

Description

technical field [0001] The invention relates to a Cronobacter zurich type 5 lipopolysaccharide O-antigen oligosaccharide fragment and a preparation method and application thereof, belonging to the technical field of anti-Cronobacter vaccine development. Background technique [0002] Cronobacter turicensis is a facultative anaerobic rod-shaped Gram-negative pathogen belonging to the genus Cronobacter spp. In 1961, Urmenyi et al. reported the infection of Cronobacter for the first time, and then this bacterium has received extensive attention from scientists (Joseph, S. et al. J. Clin. Microbiol. 2012, 50(9), 3031-3039). Cronobacter is an opportunistic pathogen widely present in food and the environment, which can cause infection of people of different age groups (such as HIV / AIDS patients) with weakened immunity, and is harmful to newborns, especially premature infants. , the greatest threat to low birth weight children. People infected by it will lead to necrotizing entero...

Claims

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Application Information

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IPC IPC(8): C07H15/12C07H1/00A61K39/385A61P31/04
CPCC07H15/12C07H1/00A61K39/385A61P31/04A61K2039/60Y02P20/55
Inventor 顾国锋庄士贤
Owner SHANDONG UNIV
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