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

Martin Rejzek, Velupillai Srikannathasan, Corin Wing, Andrew Preston, Erin L. Westman, Joseph S. Lam, James Henderson Naismith, Duncan J. Maskell, Robert A. Field

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

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 similar to 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 languageEnglish
Pages (from-to)1203-1210
Number of pages8
JournalOrganic & Biomolecular Chemistry
Volume7
Issue number6
DOIs
Publication statusPublished - 2009

Keywords

  • ENTEROBACTERIAL COMMON ANTIGEN
  • UDP-N-ACETYLGLUCOSAMINE
  • LARGE-SCALE SYNTHESIS
  • BORDETELLA-PERTUSSIS
  • ESCHERICHIA-COLI
  • BIOCHEMICAL-CHARACTERIZATION
  • PSEUDOMONAS-AERUGINOSA
  • ENGINEERED BACTERIA
  • LIPOPOLYSACCHARIDE
  • OLIGOSACCHARIDES

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