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. 1974 Dec;71(12):5022–5026. doi: 10.1073/pnas.71.12.5022

Enzymatic Utilization of P1-Di-N-acetylchitobiosyl P2-Dolichyl Pyrophosphate and Its Chemical Synthesis*

Josiah F Wedgwood †, Christopher D Warren ‡, Roger W Jeanloz ‡, Jack L Strominger †
PMCID: PMC434032  PMID: 4531034

Abstract

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-Ac2GlcNAc-P) 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.

Keywords: glycoprotein biosynthesis, lipid intermediate, mannose-containing oligosaccharide, di-N-acetylchitobiosyl phosphate

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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