Organic Chemistry: Current Research
Open Access

Abstract

Synthesis of Sialyl Lewis X Related Tetrasaccharide Library Through Random Fucosylation on a Partially Protected Trisaccharide

Yili Ding, Chamakura VNS Varaprasad, Saeed El-Ashram, Jiedan Liao, Nan Zhang and Bingyun Wang

Background

Carbohydrate recognition has been shown to be involved in various biological processes. E-selectin is expressed on the endothelial cells stimulated by cytokines, such as IL-1β or TNF-α at inflammatory sites and plays an important role in the transport of neutrophils to inflammatory sites. The tetrasaccharide SLex is distributed on the surface of neutrophils and has been shown to be a ligand recognized by E-selectin. SLex and its derivatives can block the interaction between SLex and E-selectin and will be useful as the anti-inflammatory and anti-tumor agents.

Results

Random fucosylation on a partially protected sialyl LacNAc trisaccharide, resulted in the corresponding glycosylated products as a mixture. After careful purification, debenzylation, deacetylation, alkaline hydrolysis and further purification on C-18 column, a tetrasaccharide library containing five sialyl lewis X related tetrsaccharides was obtained, and the results were confirmed by proton NMR study.

Conclusion

Random fucosylation was demonstrated as efficient method to generate sialyl related tetrasaccharide library.