Russian Chemical Bulletin

, Volume 50, Issue 7, pp 1303–1308

A novel synthesis of N-acetyl-α-d-fucosamine 1-phosphate and uridine 5"-diphospho-N-acetyl-α-d-fucosamine

  • P. A. Illarionov
  • V. I. Torgov
  • I. I. Hancock
  • V. N. Shibaev
Article

DOI: 10.1023/A:1014035613269

Cite this article as:
Illarionov, P.A., Torgov, V.I., Hancock, I.I. et al. Russian Chemical Bulletin (2001) 50: 1303. doi:10.1023/A:1014035613269

Abstract

In connection with studies on the biosynthesis of capsular polysaccharides from Staphylococcus aureus, a new synthesis of uridine 5"-(2-acetamido-2,6-dideoxy-α-d-galactopyranosyl diphosphate) (uridine 5"-diphospho-N-acetyl-α-d-fucosamine) using 2-azido-3,4-di-O-acetyl-2,6-dideoxy-α-d-galactopyranosyl nitrate as the key intermediate was carried out. The reaction of this product with cesium dibenzyl phosphate smoothly affords the corresponding β-glycosyl dibenzyl phosphate, which undergoes anomerization on treatment with BF3·Et2O and 2-bromopyridine to give α-glycosyl dibenzyl phosphate in high yield. This product was then transformed into 2-amino-3,4-di-O-acetyl-2,6-dideoxy-α-d-galactopyranosyl phosphate, subsequently converted into 2-acetamido-2,6-dideoxy-α-d-galactopyranosyl phosphate and the target nucleoside diphosphate sugar.

glycosyl phosphatessugar nucleotidesamino sugarsN-acetyl-d-fucosaminephosphorylation

Copyright information

© Plenum Publishing Corporation 2001

Authors and Affiliations

  • P. A. Illarionov
    • 1
  • V. I. Torgov
    • 1
  • I. I. Hancock
    • 2
  • V. N. Shibaev
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Medical SchoolUniversity of Newcastle, Framlington PlaceNewcastle upon TyneUnited Kingdom