Enzymatic Utilization of P 1 -Di- N -acetylchitobiosyl P 2 -Dolichyl Pyrophosphate and Its Chemical Synthesis
- 1 December 1974
- journal article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 71 (12) , 5022-5026
- https://doi.org/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.Keywords
This publication has 13 references indexed in Scilit:
- Occurrence of a β‐D‐mannopyranosyl phosphate residue in the polyprenyl mannosyl phosphate formed in calf pancreas microsomes and in human lymphocytesFEBS Letters, 1974
- The Role of a Dolichol-Oligosaccharide as an Intermediate in Glycoprotein BiosynthesisProceedings of the National Academy of Sciences, 1974
- Formation of Lipid-Bound Oligosaccharides Containing Mannose. Their Role in Glycoprotein SynthesisProceedings of the National Academy of Sciences, 1973
- Lipid intermediates of complex-polysaccharide biosynthesis. III. Chemical synthesis of ficaprenyl α-D-mannopyranosyl phosphateBiochemistry, 1973
- Membrane glycoproteins. I. Enzymatic synthesis of mannosyl phosphoryl polyisoprenol and its role as a mannosyl donor in glycoprotein synthesis.1973
- The Role of Mannosyl-phosphoryl-dihydropolyisoprenol in the Synthesis of Mammalian GlycoproteinsJournal of Biological Chemistry, 1973
- The biosynthesis of a N,N′-diacetylchitobiose containing lipid by liver microsomes. A probable dolichol pyrophosphate derivativeBiochemical and Biophysical Research Communications, 1973
- The Role of Polyprenol-Bound Saccharides as Intermediates in Glycoprotein Synthesis in LiverProceedings of the National Academy of Sciences, 1972
- The synthesis of a di-N-acetylchitobiose asparagine derivative, 2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-1-N-(4-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine.1970
- Energetics of Peptide FormationNature, 1952