Issue 6, 2009
From the journal:

Organic & Biomolecular Chemistry

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†

Martin Rejzek,ab   Velupillai Sri Kannathasan,a   Corin Wing,a   Andrew Preston,c   Erin L. Westman,d   Joseph S. Lam,d   James H. Naismith,e   Duncan J. Maskellf  and  Robert A. Field*ab  

* Corresponding authors

a School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK

b Biological Chemistry Department, John Innes Centre, Norwich Research Park, Colney Lane, Norwich, UK
E-mail: rob.field@bbsrc.ac.uk
Fax: +44 (0) 1603 450018
Tel: +44 (0) 1603 450720

c Department of Clinical Veterinary Science, University of Bristol, Langford, North Somerset, UK

d Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON, Canada

e School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, UK

f Department of Veterinary Medicine, University of Cambridge, Madingley Road, Cambridge, UK

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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Article information

DOI
https://doi.org/10.1039/B819607A
Article type
Paper
Submitted
04 Nov 2008
Accepted
08 Dec 2008
First published
02 Feb 2009

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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