Effect of anomeric linkage on the sialylation of glycosides by cells

The synthesis of sialylated glycosides using saccharide primers and cells was investigated. alpha center dot and beta center dot Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of alpha- and beta-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The beta-dodecyl galactoside primer was sialylated but the alpha-dodecyl galactoside primer was not. Both the alpha- and beta-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the alpha- or beta-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is beta-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur.