Guanosine diphosphate-4-keto-6-deoxy-D-mannose reductase in the pathway for the synthesis of GDP-6-deoxy-D-talose in Actinobacillus actinomycetemcomitans

Nao Suzuki, Yoshio Nakano, Yasuo Yoshida, Takashi Nezu, Yoshihiro Terada, Yoshihisa Yamashita, Toshihiko Koga

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The serotype a-specific polysaccharide antigen of Actinobacillus actinomycetemcomitans is an unusual sugar, 6-deoxy-D-talose. Guanosine diphosphate (GDP)-6-deoxy-D-talose is the activated sugar nucleotide form of 6-deoxy-D-talose, which has been identified as a constituent of only a few microbial polysaccharides. In this paper, we identify two genes encoding GDP-6-deoxy-D-talose synthetic enzymes, GDP-α-D-mannose 4,6-dehydratase and GDP-4-keto-6-deoxy-D-mannose reductase, in the gene cluster required for the biosynthesis of serotype a-specific polysaccharide antigen from A. actinomycetemcomitans SUNYaB 75. Both gene products were produced and purified from Escherichia coli transformed with plasmids containing these genes. Their enzymatic reactants were analysed by reversed-phase HPLC (RP-HPLC). The sugar nucleotide produced from GDP-α-D-mannose by these enzymes was purified by RP-HPLC and identified by electrospray ionization-MS, 1H nuclear magnetic resonance, and GC/MS. The results indicated that GDP-6-deoxy-D-talose is produced from GDP-α-D-mannose. This paper is the first report on the GDP-6-deoxy-D-talose biosynthetic pathway and the role of GDP-4-keto-6-deoxy-D-mannose reductase in the synthesis of GDP-6-deoxy-D-talose.

Original languageEnglish
Pages (from-to)5963-5971
Number of pages9
JournalEuropean Journal of Biochemistry
Volume269
Issue number23
DOIs
Publication statusPublished - Dec 17 2002
Externally publishedYes

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Aggregatibacter actinomycetemcomitans
Guanosine
Diphosphates
Oxidoreductases
Guanosine Diphosphate Mannose
Mannose
Polysaccharides
Sugars
Genes
4 alpha-glucanotransferase
Deoxy Sugars
Nucleotides
High Pressure Liquid Chromatography
Hydro-Lyases
Antigens
Biosynthetic Pathways
Electrospray ionization
Gene encoding
Multigene Family
L-talo-gamma-lactone

All Science Journal Classification (ASJC) codes

  • Biochemistry

Cite this

Guanosine diphosphate-4-keto-6-deoxy-D-mannose reductase in the pathway for the synthesis of GDP-6-deoxy-D-talose in Actinobacillus actinomycetemcomitans. / Suzuki, Nao; Nakano, Yoshio; Yoshida, Yasuo; Nezu, Takashi; Terada, Yoshihiro; Yamashita, Yoshihisa; Koga, Toshihiko.

In: European Journal of Biochemistry, Vol. 269, No. 23, 17.12.2002, p. 5963-5971.

Research output: Contribution to journalArticle

Suzuki, Nao ; Nakano, Yoshio ; Yoshida, Yasuo ; Nezu, Takashi ; Terada, Yoshihiro ; Yamashita, Yoshihisa ; Koga, Toshihiko. / Guanosine diphosphate-4-keto-6-deoxy-D-mannose reductase in the pathway for the synthesis of GDP-6-deoxy-D-talose in Actinobacillus actinomycetemcomitans. In: European Journal of Biochemistry. 2002 ; Vol. 269, No. 23. pp. 5963-5971.
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AU - Suzuki, Nao

AU - Nakano, Yoshio

AU - Yoshida, Yasuo

AU - Nezu, Takashi

AU - Terada, Yoshihiro

AU - Yamashita, Yoshihisa

AU - Koga, Toshihiko

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AB - The serotype a-specific polysaccharide antigen of Actinobacillus actinomycetemcomitans is an unusual sugar, 6-deoxy-D-talose. Guanosine diphosphate (GDP)-6-deoxy-D-talose is the activated sugar nucleotide form of 6-deoxy-D-talose, which has been identified as a constituent of only a few microbial polysaccharides. In this paper, we identify two genes encoding GDP-6-deoxy-D-talose synthetic enzymes, GDP-α-D-mannose 4,6-dehydratase and GDP-4-keto-6-deoxy-D-mannose reductase, in the gene cluster required for the biosynthesis of serotype a-specific polysaccharide antigen from A. actinomycetemcomitans SUNYaB 75. Both gene products were produced and purified from Escherichia coli transformed with plasmids containing these genes. Their enzymatic reactants were analysed by reversed-phase HPLC (RP-HPLC). The sugar nucleotide produced from GDP-α-D-mannose by these enzymes was purified by RP-HPLC and identified by electrospray ionization-MS, 1H nuclear magnetic resonance, and GC/MS. The results indicated that GDP-6-deoxy-D-talose is produced from GDP-α-D-mannose. This paper is the first report on the GDP-6-deoxy-D-talose biosynthetic pathway and the role of GDP-4-keto-6-deoxy-D-mannose reductase in the synthesis of GDP-6-deoxy-D-talose.

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