Enzymatic utilization of P1-di-N-acetylchitobiosyl P2-dolichyl pyrophosphate and its chemical synthesis

Proc Natl Acad Sci U S A. 1974 Dec;71(12):5022-6. doi: 10.1073/pnas.71.12.5022.

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-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.

MeSH terms

  • Cell Membrane / enzymology
  • Chromatography, Thin Layer
  • Disaccharides* / chemical synthesis
  • Disaccharides* / metabolism
  • Diterpenes* / chemical synthesis
  • Diterpenes* / metabolism
  • Glucosamine
  • Lymphocytes / enzymology
  • Mannose
  • Oligosaccharides
  • Phospholipids* / chemical synthesis
  • Phospholipids* / metabolism

Substances

  • Disaccharides
  • Diterpenes
  • Oligosaccharides
  • Phospholipids
  • Glucosamine
  • Mannose