Jiangnan University

Max Planck Institute of Colloids and Interfaces

Chunjun Qin

Jian Yin

Jing Hu

Zhonghua Liu

Peter Seeberger

The disclosure discloses a chemical synthesis method of oligosaccharides of aserotype O11 O-antigen, and belongs to the field of chemistry. The disclosure includes constructing an O-antigen trisaccharide by using a D-glucose building block, an L-fucosamine building block and a D-fucosamine building block; wherein the D-glucose building block or the L-fucosamine building block is linked with the D-fucosamine building block through a 1,2-α-cis-glycosidic bond, the D-glucose building block is linked with the L-fucosamine building block through a 1,2-β-trans-glycosidic bond, and the construction of the 1,2-α-cis-glycosidic bond is conducted in a mixed solvent; and the mixed solvent includes two or more of dichloromethane, diethyl ether and thiophene. According to the method of the disclosure, D-mannose is taken as a raw material, D-fucose is obtained simply, conveniently and efficiently, depending on suitable mixed solvents, the uniform construction of a cis-glycosidic bond of the D-fucose is achieved, the stereoselectivity can be up to 100%, and a very good application prospect in the aspects of the development of novel medicines and vaccines againstand the like is achieved.

Chemical synthesis of oligosaccharides ofserotype O11 O-antigen

Disclosed is synthesis of an O-Antigen oligosaccharide compound ofserotype O2, belonging to the field of organic synthesis. The disclosure obtains O-antigen disaccharide to tetracosasaccharide ofserotype Oby chemical synthesis. A chemical synthesis method which is quite conducive to production of a glucose-&#x3b1;-lglucosidic bond is developed in the disclosure by a protectant strategy, temperature effect, solvent effect, and additive effect. The method is applied in synthesis of an O-antigen oligosaccharide compound ofserotype O2 assembled with an amino linking arm. A saccharide conjugate can be prepared from the synthesized O-antigen oligosaccharide compound ofserotype O2 assembled with an amino linking arm together with a carrier protein for immunology researches, playing an important role in preventing and treating

Synthesis of O-antigen oligosaccharide compounds ofserotype O2

The present disclosure discloses the chemical synthesis method of theserotype O51 O-antigen oligosaccharide, belonging to the field of chemistry. Source-abundant D-glucose, L-fucose, D-glucosamine and the like are used as raw materials to prepare three glycosylation building blocks, the synthetic route composed of 11 reaction modules is designed, and through the optimization of protecting group and the optimization of the time of introducing functional group, the preparation of the target oligosaccharide chain is successfully achieved. The oligosaccharide chain prepared in the present disclosure has the advantages of cheap and easy-to-get raw materials, and simple and easy-to-repeat preparation method. The present disclosure will have good application prospects in the aspects of development of new drugs and vaccines of, and the like.

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Wuxi, China

Chunjun Qin