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

Martin Rejzek; Velupillai Sri Kannathasan; Corin Wing; Andrew Preston; Erin L Westman; Joseph S Lam; James H Naismith; Duncan J Maskell; Robert A Field

doi:10.1039/b819607a

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

Martin Rejzek, Velupillai Sri Kannathasan, Corin Wing, Andrew Preston, Erin L Westman, Joseph S Lam, James H Naismith, Duncan J Maskell, Robert A Field

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

11 Citations (SciVal)

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.

Original language	English
Pages (from-to)	1203-1210
Number of pages	8
Journal	Organic & Biomolecular Chemistry
Volume	7
Issue number	6
DOIs	https://doi.org/10.1039/b819607a
Publication status	Published - 2009

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Rejzek, M., Sri Kannathasan, V., Wing, C., Preston, A., Westman, E. L., Lam, J. S., Naismith, J. H., Maskell, D. J., & Field, R. A. (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 & Biomolecular Chemistry, 7(6), 1203-1210. https://doi.org/10.1039/b819607a

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; Sri Kannathasan, Velupillai; Wing, Corin et al.
In: Organic & Biomolecular Chemistry, Vol. 7, No. 6, 2009, p. 1203-1210.

Research output: Contribution to journal › Article › peer-review

Rejzek, M, Sri Kannathasan, V, Wing, C, Preston, A, Westman, EL, Lam, JS, Naismith, JH, Maskell, DJ & Field, RA 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 & Biomolecular Chemistry, vol. 7, no. 6, pp. 1203-1210. https://doi.org/10.1039/b819607a

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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-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.",

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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

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