title: 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.
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-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.
authors.affiliation: School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK NR4 7TJ.
authors.forename: Martin
authors.initials: M
authors.lastname: Rejzek
authors.forename: Velupillai
authors.initials: V
authors.lastname: Sri Kannathasan
authors.forename: Corin
authors.initials: C
authors.lastname: Wing
authors.forename: Andrew
authors.initials: A
authors.lastname: Preston
authors.forename: Erin L
authors.initials: EL
authors.lastname: Westman
authors.forename: Joseph S
authors.initials: JS
authors.lastname: Lam
authors.forename: James H
authors.initials: JH
authors.lastname: Naismith
authors.forename: Duncan J
authors.initials: DJ
authors.lastname: Maskell
authors.forename: Robert A
authors.initials: RA
authors.lastname: Field
mesh_terms: 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
chemical_list: D008070:Lipopolysaccharides; C540242:uridine 5'-diphospho 2,3-diacetamido-2,3-dideoxy-alpha-D-glucuronic acid; D014535:Uridine Diphosphate Glucuronic Acid