Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides (original) (raw)

Bioorganic & Medicinal Chemistry, 2005

Abstract

Complex multifucosylated oligosaccharides are structural elements of glycoprotein and glycolipid subsets of larval, egg, and adult stages of Schistosoma, the parasitic worms that cause schistosomiasis, a serious disease affecting more than 200 million people in the tropics. The fucosylated structures are thought to play an important role in the immunology of schistosomiasis. Defined schistosomal oligosaccharides that enable immunological studies are difficult to obtain from natural sources. Therefore, we have chemically synthesized spacer-linked GlcNAc, Fucα1-3GlcNAc, Fucα1-2Fucα1-3GlcNAc, and Fucα1-2Fucα1-2Fucα1-3GlcNAc. This series of linear oligosaccharides was used to screen a library of anti-schistosome monoclonal antibodies by surface plasmon resonance spectroscopy. Interestingly, the reactive antibodies could be grouped according to their specificity for the different oligosaccharides tested, showing that these oligosaccharides form different immunological entities based on the number and linkage of the fucose residues. Subsequently, the thus defined monoclonal antibodies were used to visualize the expression of the corresponding oligosaccharide epitopes by adult Schistosoma mansoni worms.Several linear fucose-containing oligosaccharides have been synthesized, conjugated to BSA and were used to screen a library of anti-schistosome monoclonal antibodies.

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