Synthesis and evaluation of synthetic analogues of dolichyl-P-P-chitobiose as oligosaccharyltransferase substrates

Five analogues of dolichylpyrophosphorylchitobiose containing short, well defined lipid components were synthesized and evaluated as substrates for yeast oligosaccharyltransferase. All of the modified lipids led to a large decrease in enzyme-catalyzed glycosylation of the peptide substrate, BzAsnLeuThrNH2, thus indicating a critical role for the polyisoprene, dolichol, in anchoring the oligosaccharide donor during catalysis.