Efficient Synthesis of Partially Protected Neu5Ac α(2-3) Gal β(1-3) GlcNAc Related Trisaccharide

Title:Efficient Synthesis of Partially Protected Neu5Ac α(2-3) Gal β(1-3) GlcNAc Related Trisaccharide

Volume: 15 Issue: 8

Author(s): Yili Ding*, Chamakura V.N.S. Vara Prasad , Shujian Huang and Bingyun Wang

Affiliation:

• Life Science Department, Foshan University, Foshan, Guangdong 528000,China

Keywords: Neu5Acα2-3Galβ1-3GlcNAc trisaccharide, synthesis, glycosylation, combinatorial chemistry, oligosaccharide, virus.

Abstract: Background: The interaction between viral HA (hemagglutinin) and oligosaccharide of the host plays an important role in the infection and transmission of avian and human flu viruses, and H5N1 studies showed that the H5N1 duck viruses bound with the highest affinity to trisaccharide Neu5Acα2-3Galβ1-3GlcNAc, H5N1 chicken and human viruses isolated in 1997 in Hong Kong were found to bind the sulfated trisaccharide Neu5Acα2-3Galβ1-4(6-HSO3)GlcNAc with the extraordinary high affinity, and this necessitates the synthesis of sulfated Neu5Acα2-3Galβ1-3GlcNAc library for screening in search of active ligands against of H5N1 virus.

Results: Random sulfation of partially protected Neu5Acα2-3Galβ1-3GlcNAc trisaccharide may afford the mono-sulfated and di-sulfated Neu5Acα2-3Galβ1-3GlcNAc libraries for screening their anti-H5N1 activity. In order to synthesize the sulfated library of (Neu5Acα2-3Galβ1-3GlcNAc) trisaccharide, the efficient synthesis of corresponding partially protected Neu5Acα2-3Galβ1-3GlcNAc trisaccharide is an immediate necessity and this target was achieved in an efficient manner.

Conclusion: By suitably maneuvering protecting groups on the nitrogen in Galβ1-3GlcNAc related disaccharide acceptors, partially protected Neu5Acα2-3Galβ1-3GlcNAc trisaccharide was efficiently synthesized. It is believed that the strategy followed herein provides a general method for synthesizing useful sialyl acid related oligosaccharides.

Cite this article as:

Ding Yili *, Vara Prasad V.N.S. Chamakura , Huang Shujian and Wang Bingyun , Efficient Synthesis of Partially Protected Neu5Ac α(2-3) Gal β(1-3) GlcNAc Related Trisaccharide, Letters in Organic Chemistry 2018; 15 (8) . https://dx.doi.org/10.2174/1570178614666171129155756