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.
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.
Rejzek
Martin
M
School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK NR4 7TJ.
Sri Kannathasan
Velupillai
V
Wing
Corin
C
Preston
Andrew
A
Westman
Erin L
EL
Lam
Joseph S
JS
Naismith
James H
JH
Maskell
Duncan J
DJ
Field
Robert A
RA
D042483:Bordetella parapertussis / Q000378:metabolism* / Q000472:pathogenicity; D002236:Carbohydrate Conformation; D006801:Humans; D008070:Lipopolysaccharides / Q000096:biosynthesis* / Q000737:chemistry; D011550:Pseudomonas aeruginosa / Q000378:metabolism* / Q000472:pathogenicity; D013237:Stereoisomerism; D014535:Uridine Diphosphate Glucuronic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D008070:Lipopolysaccharides; C540242:uridine 5'-diphospho 2,3-diacetamido-2,3-dideoxy-alpha-D-glucuronic acid; D014535:Uridine Diphosphate Glucuronic Acid