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Enzymatic Utilization of P1-Di-N-acetylchitobiosyl P2-Dolichyl Pyrophosphate and its Chemical Synthesis
Josiah F. Wedgwood, Christopher D. Warren, Roger W. Jeanloz and Jack L. Strominger
Proceedings of the National Academy of Sciences of the United States of America
Vol. 71, No. 12 (Dec., 1974), pp. 5022-5026
Published by: National Academy of Sciences
Stable URL: http://www.jstor.org/stable/63962
Page Count: 5
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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-β -D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy - α ,β -D-glucopyranosyl phosphate (Ac3GlcNAc-Ac2GlcNAcP) was isolated by preparative thin layer chromatography. Treatment of this compound with P1-diphenyl P2-dolichyl pyrophosphate gave an acetylated pyrophosphate diester, which was purified chromatographically and deacetylated. The product, P1-di-N-acetylchitobiosyl P2-dolichyl pyrophosphate (Dol-P-P-GlcNAc-GlcNAc), was readily separated from P1-2-acetamido-2-deoxy-α -D-glucopyranosyl P2-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 © 1974 National Academy of Sciences