Enzymatic Utilization of P1-Di-N-acetylchitobiosyl P2-Dolichyl Pyrophosphate and Its Chemical Synthesis
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.
- Publication:
-
Proceedings of the National Academy of Science
- Pub Date:
- December 1974
- DOI:
- 10.1073/pnas.71.12.5022
- Bibcode:
- 1974PNAS...71.5022W