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Issue 6, 2009
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Chemical synthesis of UDP-Glc-2,3-diNAcA, a key intermediate in cell surfacepolysaccharide biosynthesis in the human respiratory pathogens B. pertussis and P. aeruginosa

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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-α-D-glucuronic acid (UDP-Glc-2,3-diNAcA) (1) from N-acetyl-D-glucosamine in 17 steps and ∼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.

Graphical abstract: 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

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Publication details

The article was received on 04 Nov 2008, accepted on 08 Dec 2008 and first published on 02 Feb 2009


Article type: Paper
DOI: 10.1039/B819607A
Org. Biomol. Chem., 2009,7, 1203-1210

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    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 and R. A. Field, Org. Biomol. Chem., 2009, 7, 1203
    DOI: 10.1039/B819607A

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