Hydrophobic glycosides of N-acetylglucosamine can act as primers for polylactosamine synthesis and can affect glycolipid synthesis in vivo

Several hydrophobic glycosides of N-acetylglucosamine (GlcNAc) served as primers for polylactosamine synthesis when added to Chinese hamster ovary (CHO) cells. The modified glycosides, containing one to six lactosamine repeats in linear array, were sialylated and secreted into the culture medium. The relative efficiencies of the glycosides to serve as primers were dependent on the nature of the aglycone and on the anomeric cofiguration of the GlcNAc residue. The same compounds were tested for their effects on glycolipid synthesis in CHO cells. All of the β-glycosides significantly inhibited the synthesis of the lacto-series glycolipid G(M3) whereas the α-glycoside was inactive. The compound GlcNAcα1-O-benzyl was the most efficient primer of polylactosamine synthesis and had no effect on glycolipid synthesis. This compound may have potential for the assay of the polylactosamine synthetic capacity of living cells.