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Fully acetylated chitobiose was treated with phosphoric acid to give a mixture of products from which 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta- D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-alpha,beta- D-glucopyranosyl phosphate (Ac(3)GlcNAc-Ac(2)GlcNAc-P) was isolated by preparative thin layer chromatography. Treatment of this compound with P(1)-diphenyl P(2)-dolichyl pyrophosphate gave an acetylated pyrophosphate diester, which was purified chromatographically and deacetylated. The product, P(1)-di-N-acetylchitobiosyl P(2)-dolichyl pyrophosphate (Dol-P-P-GlcNAc-GlcNAc), was readily separated from P(1)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl P(2)-dolichyl pyrophosphate (Dol-P-P-GlcNAc) by thin layer chromatography in several solvent systems. Addition of this compound to human lymphocyte membrane preparations led to the formation of a mannose-containing derivative which appears to be an oligosaccharide phospholipid, as judged by its behavior on DEAE-cellulose chromatography and by its hydrolysis to give an oligosaccharide containing more than four monosaccharide units.

proceedings of the national academy of sciences of the united states of america

Enzymatic Utilization of P 1 -Di- N -acetylchitobiosyl P 2 -Dolichyl Pyrophosphate and Its Chemical Synthesis