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

M. Rejzek; V.S. Kannathasan; C. Wing; A. Preston; E.L. Westman; J.S. Lam; J.H. Naismith; D.J. Maskell; R.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

M. Rejzek, V.S. Kannathasan, C. Wing, A. Preston, E.L. Westman, J.S. Lam, J.H. Naismith, D.J. Maskell, R.A. Field

Manchester Institute of Biotechnology

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

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	Undefined
Pages (from-to)	1203-1210
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	7
DOIs	https://doi.org/10.1039/b819607a
Publication status	Published - 2009

Keywords

Bordetella parapertussis
Carbohydrate conformation
Lipopolysaccharides
Pseudomonas aeruginosa
Stereoisomerism
Uridine Diphosphate Glucuronic Acid

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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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, 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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author = "M. Rejzek and V.S. Kannathasan and C. Wing and A. Preston and E.L. Westman and J.S. Lam and J.H. Naismith and D.J. Maskell and R.A. Field",

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doi = "10.1039/b819607a",

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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, pp. 1203-1210. https://doi.org/10.1039/b819607a

TY - JOUR

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

AU - Rejzek, M.

AU - Kannathasan, V.S.

AU - Wing, C.

AU - Preston, A.

AU - Westman, E.L.

AU - Lam, J.S.

AU - Naismith, J.H.

AU - Maskell, D.J.

AU - Field, R.A.

PY - 2009

Y1 - 2009

N2 - 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.

AB - 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.

KW - Bordetella parapertussis

KW - Carbohydrate conformation

KW - Lipopolysaccharides

KW - Pseudomonas aeruginosa

KW - Stereoisomerism

KW - Uridine Diphosphate Glucuronic Acid

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UR - https://www.scopus.com/pages/publications/62249218237

U2 - 10.1039/b819607a

DO - 10.1039/b819607a

M3 - Article

SN - 1477-0520

VL - 7

SP - 1203

EP - 1210

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

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

Keywords

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UN SDGs

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