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

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

11 Citations (Scopus)

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-α-D-glucuronic acid (UDP-Glc-2,3-diNAcA) (1) from N-acetyl-D-glucosamine in 17 steps and ∼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 and Biomolecular Chemistry
Volume	7
Issue number	6
DOIs	https://doi.org/10.1039/b819607a
Publication status	Published - 2009

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Rejzek, M., Kannathasan, V. S., 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 and Biomolecular Chemistry, 7(6), 1203-1210. https://doi.org/10.1039/b819607a

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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-α-D-glucuronic acid (UDP-Glc-2,3-diNAcA) (1) from N-acetyl-D-glucosamine in 17 steps and ∼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.",

author = "Martin Rejzek and Kannathasan, {Velupillai Sri} and Corin Wing and Andrew Preston and Westman, {Erin L.} and Lam, {Joseph S.} and Naismith, {James H.} and Maskell, {Duncan J.} and Field, {Robert A.}",

year = "2009",

doi = "10.1039/b819607a",

language = "English",

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journal = "Organic and Biomolecular Chemistry",

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Rejzek, M, Kannathasan, VS, 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 and Biomolecular Chemistry, vol. 7, no. 6, pp. 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; Kannathasan, Velupillai Sri; Wing, Corin et al.
In: Organic and Biomolecular Chemistry, Vol. 7, No. 6, 2009, p. 1203-1210.

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

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T1 - 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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AU - Kannathasan, Velupillai Sri

AU - Wing, Corin

AU - Preston, Andrew

AU - Westman, Erin L.

AU - Lam, Joseph S.

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AU - Maskell, Duncan J.

AU - Field, Robert A.

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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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