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 Srikannathasan; Corin Wing; Andrew Preston; Erin L. Westman; Joseph S. Lam; James Henderson 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 Srikannathasan, Corin Wing, Andrew Preston, Erin L. Westman, Joseph S. Lam, James Henderson Naismith, Duncan J. Maskell, Robert A. Field

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 similar to 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

Keywords

ENTEROBACTERIAL COMMON ANTIGEN
UDP-N-ACETYLGLUCOSAMINE
LARGE-SCALE SYNTHESIS
BORDETELLA-PERTUSSIS
ESCHERICHIA-COLI
BIOCHEMICAL-CHARACTERIZATION
PSEUDOMONAS-AERUGINOSA
ENGINEERED BACTERIA
LIPOPOLYSACCHARIDE
OLIGOSACCHARIDES

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Rejzek, M., Srikannathasan, 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

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

keywords = "ENTEROBACTERIAL COMMON ANTIGEN, UDP-N-ACETYLGLUCOSAMINE, LARGE-SCALE SYNTHESIS, BORDETELLA-PERTUSSIS, ESCHERICHIA-COLI, BIOCHEMICAL-CHARACTERIZATION, PSEUDOMONAS-AERUGINOSA, ENGINEERED BACTERIA, LIPOPOLYSACCHARIDE, OLIGOSACCHARIDES",

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

year = "2009",

doi = "10.1039/b819607a",

language = "English",

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pages = "1203--1210",

journal = "Organic & Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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Rejzek, M, Srikannathasan, 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

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; Srikannathasan, 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

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AU - Srikannathasan, Velupillai

AU - Wing, Corin

AU - Preston, Andrew

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AU - Lam, Joseph S.

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AU - Field, Robert A.

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KW - LARGE-SCALE SYNTHESIS

KW - BORDETELLA-PERTUSSIS

KW - ESCHERICHIA-COLI

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KW - PSEUDOMONAS-AERUGINOSA

KW - ENGINEERED BACTERIA

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DO - 10.1039/b819607a

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SN - 1477-0539

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EP - 1210

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 6

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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