Chemical synthesis of UDP-Glc-2,3-diNAcA, a key intermediate in cell surface polysaccharide biosynthesis in the human respiratory pathogens B. pertussis and P. aeruginosa

M. Rejzek, V.S. Kannathasan, C. Wing, A. Preston, E.L. Westman, J.S. Lam, J.H. Naismith, D.J. Maskell, R.A. Field

Research output: Contribution to journalArticlepeer-review


In connection with studies on lipopolysaccharide biosynthesis in respiratory pathogens we had a need to access potential biosynthetic intermediate sugar nucleotides. Herein we report the chemical synthesis of uridine 5'-diphospho 2,3-diacetamido-2,3-dideoxy-alpha-D-glucuronic acid (UDP-Glc-2,3-diNAcA) (1) from N-acetyl-D-glucosamine in 17 steps and approximately 9% overall yield. This compound has proved invaluable in the elucidation of biosynthetic pathways leading to the formation of 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid-containing polysaccharides.
Original languageUndefined
Pages (from-to)1203-1210
Number of pages8
JournalOrganic and Biomolecular Chemistry
Publication statusPublished - 2009


  • Bordetella parapertussis
  • Carbohydrate conformation
  • Lipopolysaccharides
  • Pseudomonas aeruginosa
  • Stereoisomerism
  • Uridine Diphosphate Glucuronic Acid

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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