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 Sri Kannathasan, Corin Wing, Andrew Preston, Erin L Westman, Joseph S Lam, James H Naismith, Duncan J Maskell, Robert A Field

Research output: Contribution to journalArticle

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

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