A novel N-acetylglucosaminyl polyprene in hen oviduct

Incubation of hen oviduct membranes with UDP-[14C]N-acetylglucosamine (GlcNAc) leads to the formation of four endogenously labeled lipids. One of these lipids has not previously been characterized. Based on its chromatographic behavior on SG-81 paper and DEAE-cellulose, it is a monophosphate diester. The oviduct lipid is extremely sensitive to mild acid hydrolysis and, based on a comparison with alpha-GlcNAc-phosphoryl-undecaprenol from Bacillus cereus, the oviduct lipid contains GlcNAc linked to a polyisoprene as the beta anomer, the polyisoprene containing an alpha-unsaturated isoprene unit. Molecular sieve chromatography indicates that the molecular weight of the lipid is on the order of mannosyl-phosphoryl-dolichol and larger than alpha-GlcNAc-phosphoryl-undecaprenol. Formation of the GlcNAc-lipid is insensitive to tunicamycin. Dolichyl phosphate stimulates formation of a GlcNAc-lipid with similar chromatographic properties.