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

Rejzek, Martin, Kannathasan, Velupillai Sri, Wing, Corin, Preston, Andrew, Westman, Erin L., Lam, Joseph S., Naismith, James H., Maskell, Duncan J. and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2009) 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. Organic and Biomolecular Chemistry, 7 (6). pp. 1203-1210. ISSN 1477-0520

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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.

Item Type:	Article
Uncontrolled Keywords:	biochemistry,physical and theoretical chemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology Faculty of Science > School of Biological Sciences
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic and Medicinal Chemistry
Related URLs:	https://www.scopus.com/pages/publication...
Depositing User:	LivePure Connector
Date Deposited:	06 Sep 2024 13:35
Last Modified:	18 Jun 2026 20:20
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96600
DOI:	10.1039/b819607a

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