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

摘要

Background: The interaction between viral HA (hemagglutinin) and oligosaccharide of thehost plays an important role in the infection and transmission of avian and human flu viruses, andH5N1 studies showed that the H5N1 duck viruses bound with the highest affinity to trisaccharideNeu5Acα2-3Galβ1-3GlcNAc, H5N1 chicken and human viruses isolated in 1997 in Hong Kong werefound to bind the sulfated trisaccharide Neu5Acα2-3Galβ1-4(6-HSO3)GlcNAc with the extraordinaryhigh affinity, and this necessitates the synthesis of sulfated Neu5Acα2-3Galβ1-3GlcNAc library forscreening in search of active ligands against of H5N1 virus.Results: Random sulfation of partially protected Neu5Acα2-3Galβ1-3GlcNAc trisaccharide may affordthe mono-sulfated and di-sulfated Neu5Acα2-3Galβ1-3GlcNAc libraries for screening their anti-H5N1activity. In order to synthesize the sulfated library of (Neu5Acα2-3Galβ1-3GlcNAc) trisaccharide, theefficient synthesis of corresponding partially protected Neu5Acα2-3Galβ1-3GlcNAc trisaccharide is animmediate necessity and this target was achieved in an efficient manner.Conclusion: By suitably maneuvering protecting groups on the nitrogen in Galβ1-3GlcNAc related disaccharideacceptors, partially protected Neu5Acα2-3Galβ1-3GlcNAc trisaccharide was efficientlysynthesized. It is believed that the strategy followed herein provides a general method for synthesizinguseful sialyl acid related oligosaccharides.