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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bordetella parapertussis / metabolism*
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Bordetella parapertussis / pathogenicity
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Carbohydrate Conformation
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Humans
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Lipopolysaccharides / biosynthesis*
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Lipopolysaccharides / chemistry
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Pseudomonas aeruginosa / metabolism*
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Pseudomonas aeruginosa / pathogenicity
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Stereoisomerism
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Uridine Diphosphate Glucuronic Acid / analogs & derivatives*
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Uridine Diphosphate Glucuronic Acid / chemical synthesis
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Uridine Diphosphate Glucuronic Acid / metabolism
Substances
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Lipopolysaccharides
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uridine 5'-diphospho 2,3-diacetamido-2,3-dideoxy-alpha-D-glucuronic acid
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Uridine Diphosphate Glucuronic Acid