Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: pertussis (whooping cough) [ICD11:
1C12.Z 
, ICD11:
XN9W3 ];
infection due to Bordetella pertussis [ICD11:
XN23B ]
The structure was elucidated in this paperNCBI PubMed ID: 19262941Journal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: rob.field
bbsrc.ac.uk
Institutions: School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UKNR4 7TJ
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) () 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.
lipopolysaccharide biosynthesis, Bordetella pertussis, pathway, surface polysaccharide, chemical synthesis, sugar nucleotide
Structure type: monomer
Location inside paper: p.1204, fig. 3,1
Trivial name: UDP-2,3-diacetamido-2,3-dideoxy-α-D-glucuronic acid, UDP-GlcNAc(3NAc)A, UDP-Glc-2,3-diNAcA, UDP-D-GlcNAc3NAcA
Methods: 13C NMR, 1H NMR, TLC, 31P NMR, ESI-MS, chemical methods, NMR-1D, HPLC
Synthetic data: chemical
Comments, role: UDP-Glc-2,3-diNAcA was synthesised in 17, steps with 9% yield.
Related record ID(s): 21685, 23332, 23821, 24072, 24198, 24263, 25734, 25866
NCBI Taxonomy refs (TaxIDs): 520
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error