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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

D-Mannuronate     (2S,3S,4S,5S)-3,4,5,6- tetrahydroxyoxane-2...

Synonyms: Mannonic acid, AG-G-68413, SureCN3178574, CTK5C9017, AC1L97Q2, ...
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Disease relevance of C02024


High impact information on C02024

  • The 13C-n.m.r. data also provided independent evidence for acetylation on D-mannuronate residues and for the ratio of D-mannuronate to L-guluronate residues in newly synthesized alginate, which had previously been determined only for material secreted from bacteria into the extracellular medium [3].
  • The structure of alginate, a linear polymer of beta1-4-linked O-acetylated d-mannuronate (M) and l-guluronate (G), is important for its activity as a virulence factor [4].
  • D-Glucuronic and D-mannuronic acid-type 1-N-iminosugars, (3S,4R,5R, 6R)- and (3S,4R,5R,6S)-4, 5-dihydroxy-6-trifluoroacetamido-3-piperidinecarboxylic acid, were proven to be potent inhibitors for beta-D-glucuronidase (IC(50) 6.5 x 10(-)(8)M) and to affect human heparanase (endo-beta-glucuronidase) [5].
  • Proton nuclear magnetic resonance spectroscopy showed that polymers produced by strains deficient in algIJF still contained a mixture of D-mannuronate and L-guluronate, indicating that C-5 epimerization was not affected [6].
  • In this study, we tested the hypothesis that the product of algG is a C5-epimerase that directly converts D-mannuronate to L-guluronate [2].

Biological context of C02024

  • A considerable decrease in intensity of the D-mannuronic acid residue signal was detected after hydrolysis of alginate lyase VI on poly-(ManUA-GulUA), but not poly(GulUA) [7].

Anatomical context of C02024

  • In this study, we show that several well-defined polysaccharides, including polymers with different sizes of beta 1-4-linked D-mannuronic acid (poly-M, high-M alginate, and M-blocks) and cellulose oxidized in the C-6 position, induced human monocytes to produce tumor necrosis factor alpha (TNF-alpha) [8].


  1. Induction of tumor necrosis factor production from monocytes stimulated with mannuronic acid polymers and involvement of lipopolysaccharide-binding protein, CD14, and bactericidal/permeability-increasing factor. Jahr, T.G., Ryan, L., Sundan, A., Lichenstein, H.S., Skjåk-Braek, G., Espevik, T. Infect. Immun. (1997) [Pubmed]
  2. Pseudomonas aeruginosa AlgG is a polymer level alginate C5-mannuronan epimerase. Franklin, M.J., Chitnis, C.E., Gacesa, P., Sonesson, A., White, D.C., Ohman, D.E. J. Bacteriol. (1994) [Pubmed]
  3. The use of 13C-n.m.r. spectroscopy to monitor alginate biosynthesis in mucoid Pseudomonas aeruginosa. Narbad, A., Hewlins, M.J., Gacesa, P., Russell, N.J. Biochem. J. (1990) [Pubmed]
  4. Epimerase active domain of Pseudomonas aeruginosa AlgG, a protein that contains a right-handed beta-helix. Douthit, S.A., Dlakic, M., Ohman, D.E., Franklin, M.J. J. Bacteriol. (2005) [Pubmed]
  5. Flexible synthesis and biological activity of uronic acid-type gem-diamine 1-N-iminosugars: a new family of glycosidase inhibitors. Nishimura, Y., Shitara, E., Adachi, H., Toyoshima, M., Nakajima, M., Okami, Y., Takeuchi, T. J. Org. Chem. (2000) [Pubmed]
  6. Identification of algI and algJ in the Pseudomonas aeruginosa alginate biosynthetic gene cluster which are required for alginate O acetylation. Franklin, M.J., Ohman, D.E. J. Bacteriol. (1996) [Pubmed]
  7. A study of the reaction catalysed by alginate lyase VI from the sea mollusc, Littorina sp. Favorov, V.V., Vozhova, E.I., Denisenko, V.A., Elyakova, L.A. Biochim. Biophys. Acta (1979) [Pubmed]
  8. Similar mechanisms of action of defined polysaccharides and lipopolysaccharides: characterization of binding and tumor necrosis factor alpha induction. Otterlei, M., Sundan, A., Skjåk-Braek, G., Ryan, L., Smidsrød, O., Espevik, T. Infect. Immun. (1993) [Pubmed]
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