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Chemical Compound Review

GDP-Fuc     [5-(2-amino-6-oxo-3H-purin-9- yl)-3,4...

Synonyms: GDP-fucose, G4401_SIGMA, KST-1A1835, AR-1A9107, AC1L199J, ...
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Disease relevance of guanosine diphosphate fucose


High impact information on guanosine diphosphate fucose

  • The MUR1 gene of Arabidopsis thaliana encodes an isoform of GDP-D-mannose-4,6-dehydratase, catalyzing the first step in the de novo synthesis of GDP-L-fucose [4].
  • To investigate the effect of GDP-L-fucose on core fucosylation, FX cDNA was transfected into Hep3B cells, which express a relatively low level of GDP-L-fucose:N-acetyl-beta-D-glucosaminide alpha1-6 fucosyltransferase (alpha1-6 FucT) and FX mRNA [1].
  • The level of GDP-L-fucose in HCC decreased in proportion with tumor size (r = -0.675, P = 0.0002) [1].
  • Transfection of this gene caused an increase in GDP-L-fucose levels as well as the extent of fucosylation on glycoproteins, including alpha-fetoprotein, as judged by reactivity to lectins [1].
  • This finding demonstrates that the decrease in GDP-l-fucose levels in the fibroblast Golgi caused by the LAD II defect does not impair bulk protein O-fucosylation, but severely affects the bulk addition of fucose as a terminal modification of N-linked glycans [5].

Chemical compound and disease context of guanosine diphosphate fucose


Biological context of guanosine diphosphate fucose

  • Thus, an elevation in GDP-L-fucose levels and the up-regulation of FX expression represent potential markers for HCC [1].
  • When expression of the series of genes responsible for GDP-L-fucose synthesis was investigated, the gene expression of FX was found to be increased in 70% (7 of 10) of the HCC tissues examined compared with that in their surrounding tissues [1].
  • As described here, PBCV-1 also encodes two open reading frames that resemble bacterial and mammalian enzymes involved in de novo GDP-L-fucose biosynthesis [8].
  • We report here the application of a genetic approach to identify and isolate human DNA sequences controlling the expression of a GDP-L-fucose: beta-D-galactoside 2-alpha-L-fucosyltransferase [alpha-1,2)fucosyltransferase) [9].
  • We previously sequenced the E. coli colanic acid gene cluster and identified one of the GDP-L-fucose biosynthetic pathway genes, gmd [10].

Anatomical context of guanosine diphosphate fucose

  • Several cell-surface antigens, including the leukocyte Lewis system and cell-surface antigens in pathogenic bacteria, depend on the availability of GDP-l-fucose for their expression [11].
  • The wide expression of both enzymes can also be observed from the large amount of data collected from a number of expressed sequence tag libraries, which indicate that not only the de novo pathway alone, but also the salvage pathway, could have a significant role in the synthesis of GDP-L-fucose in the cytosol [12].
  • It is shown that the enzymatic activities responsible for the conversion of GDP-D-mannose into GDP-L-fucose is recovered only in oocytes and is not present in the other coelomic cells (i.e. coelomocytes) [13].
  • Purification and characterization of secretory-type GDP-L-fucose: beta-D-galactoside 2-alpha-L-fucosyltransferase from human gastric mucosa [14].
  • The triazine dyes: Cibacron Blue 3GA, Reactive Red 120, Reactive Yellow 86, Reactive Green 19, Reactive Blue 4, Reactive Brown 10 inhibited the activity of a purified preparation of alpha1,6fucosyltransferase (GDP-L-fucose: N-acetyl beta-glucosaminide 6-alpha-L-fucosyltransferase, EC from human blood platelets [15].

Associations of guanosine diphosphate fucose with other chemical compounds


Gene context of guanosine diphosphate fucose

  • By contrast, the transcript encoding the FX protein, which forms GDP-L-fucose from the ketosugar intermediate produced by GMD, is present in increased amounts in the Lec13 cells [19].
  • We report here the cloning and expression of murine L-fucokinase and GDP-L-fucose pyrophosphorylase [12].
  • Crystal structure of a tetrameric GDP-D-mannose 4,6-dehydratase from a bacterial GDP-D-rhamnose biosynthetic pathway [20].
  • GDP-D-mannose dehydratase (GMD) catalyzes the first step of the pathway that converts GDP-D-mannose to GDP-L-fucose in bacteria, plants and mammals [21].
  • Here, we cloned the two key enzymes of GDP-l-fucose synthesis, H. pylori gmd coding for GDP-d-mannose dehydratase (GMD), and gmer coding for GDP-4-keto-6-deoxy-d-mannose-3,5-epimerase/4-reductase (GMER) and expressed them in an enzymatically active form in Saccharomyces cerevisiae [3].

Analytical, diagnostic and therapeutic context of guanosine diphosphate fucose

  • The fluorescent intensity of the fucosylated reaction product, which was analyzed by isocratic reverse phase HPLC, was proportional to the level of GDP-L-fucose in the microsomal fractions over the range 0.20-10 pmol [22].
  • The tissue distribution of murine L-fucokinase and GDP-L-fucose pyrophosphorylase was investigated by quantitative real time PCR, which revealed high expression of L-fucokinase and GDP-L-fucose pyrophosphorylase in various tissues [12].
  • An enzymatic method of analysis for GDP-L-fucose in biological samples, involving high-performance liquid chromatography [22].
  • Using the differential display technology, it was shown that ligation of E48 on tumor cells by the corresponding antibodies (serving as a surrogate for an as yet unidentified E48 ligand) upregulates an enzyme (FX) involved in the biosynthesis of GDP-L-fucose [23].


  1. Relationship between elevated FX expression and increased production of GDP-L-fucose, a common donor substrate for fucosylation in human hepatocellular carcinoma and hepatoma cell lines. Noda, K., Miyoshi, E., Gu, J., Gao, C.X., Nakahara, S., Kitada, T., Honke, K., Suzuki, K., Yoshihara, H., Yoshikawa, K., Kawano, K., Tonetti, M., Kasahara, A., Hori, M., Hayashi, N., Taniguchi, N. Cancer Res. (2003) [Pubmed]
  2. Identification of two GDP-6-deoxy-D-lyxo-4-hexulose reductases synthesizing GDP-D-rhamnose in Aneurinibacillus thermoaerophilus L420-91T. Kneidinger, B., Graninger, M., Adam, G., Puchberger, M., Kosma, P., Zayni, S., Messner, P. J. Biol. Chem. (2001) [Pubmed]
  3. Cloning and expression of Helicobacter pylori GDP-l-fucose synthesizing enzymes (GMD and GMER) in Saccharomyces cerevisiae. Järvinen, N., Mäki, M., Räbinä, J., Roos, C., Mattila, P., Renkonen, R. Eur. J. Biochem. (2001) [Pubmed]
  4. The MUR1 gene of Arabidopsis thaliana encodes an isoform of GDP-D-mannose-4,6-dehydratase, catalyzing the first step in the de novo synthesis of GDP-L-fucose. Bonin, C.P., Potter, I., Vanzin, G.F., Reiter, W.D. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  5. Differential terminal fucosylation of N-linked glycans versus protein O-fucosylation in leukocyte adhesion deficiency type II (CDG IIc). Sturla, L., Rampal, R., Haltiwanger, R.S., Fruscione, F., Etzioni, A., Tonetti, M. J. Biol. Chem. (2003) [Pubmed]
  6. The metabolism of 6-deoxyhexoses in bacterial and animal cells. Tonetti, M., Sturla, L., Bisso, A., Zanardi, D., Benatti, U., De Flora, A. Biochimie (1998) [Pubmed]
  7. GDP-4-keto-6-deoxy-D-mannose epimerase/reductase from Escherichia coli, a key enzyme in the biosynthesis of GDP-L-fucose, displays the structural characteristics of the RED protein homology superfamily. Rizzi, M., Tonetti, M., Vigevani, P., Sturla, L., Bisso, A., Flora, A.D., Bordo, D., Bolognesi, M. Structure (1998) [Pubmed]
  8. Paramecium bursaria Chlorella virus 1 encodes two enzymes involved in the biosynthesis of GDP-L-fucose and GDP-D-rhamnose. Tonetti, M., Zanardi, D., Gurnon, J.R., Fruscione, F., Armirotti, A., Damonte, G., Sturla, L., De Flora, A., Van Etten, J.L. J. Biol. Chem. (2003) [Pubmed]
  9. Stable expression of blood group H determinants and GDP-L-fucose: beta-D-galactoside 2-alpha-L-fucosyltransferase in mouse cells after transfection with human DNA. Ernst, L.K., Rajan, V.P., Larsen, R.D., Ruff, M.M., Lowe, J.B. J. Biol. Chem. (1989) [Pubmed]
  10. Identification of the fucose synthetase gene in the colanic acid gene cluster of Escherichia coli K-12. Andrianopoulos, K., Wang, L., Reeves, P.R. J. Bacteriol. (1998) [Pubmed]
  11. Probing the catalytic mechanism of GDP-4-keto-6-deoxy-d-mannose Epimerase/Reductase by kinetic and crystallographic characterization of site-specific mutants. Rosano, C., Bisso, A., Izzo, G., Tonetti, M., Sturla, L., De Flora, A., Bolognesi, M. J. Mol. Biol. (2000) [Pubmed]
  12. Cloning and expression of murine enzymes involved in the salvage pathway of GDP-L-fucose. Niittymäki, J., Mattila, P., Roos, C., Huopaniemi, L., Sjöblom, S., Renkonen, R. Eur. J. Biochem. (2004) [Pubmed]
  13. Study of the conversion of GDP-mannose into GDP-fucose in Nereids: a biochemical marker of oocyte maturation. Bulet, P., Hoflack, B., Porchet, M., Verbert, A. Eur. J. Biochem. (1984) [Pubmed]
  14. Purification and characterization of secretory-type GDP-L-fucose: beta-D-galactoside 2-alpha-L-fucosyltransferase from human gastric mucosa. Masutani, H., Kimura, H. J. Biochem. (1995) [Pubmed]
  15. Triazine dyes as inhibitors and affinity ligands of glycosyltransferases. Kamińska, J., Dziecioł, J., Kościelak, J. Glycoconj. J. (1999) [Pubmed]
  16. Decreased availability of GDP-L-fucose in a patient with LAD II with normal GDP-D-mannose dehydratase and FX protein activities. Körner, C., Linnebank, M., Koch, H.G., Harms, E., von Figura, K., Marquardt, T. J. Leukoc. Biol. (1999) [Pubmed]
  17. Structure of the MUR1 GDP-mannose 4,6-dehydratase from Arabidopsis thaliana: implications for ligand binding and specificity. Mulichak, A.M., Bonin, C.P., Reiter, W.D., Garavito, R.M. Biochemistry (2002) [Pubmed]
  18. The de novo synthesis of GDP-fucose is essential for flagellar adhesion and cell growth in Trypanosoma brucei. Turnock, D.C., Izquierdo, L., Ferguson, M.A. J. Biol. Chem. (2007) [Pubmed]
  19. Molecular cloning and expression of GDP-D-mannose-4,6-dehydratase, a key enzyme for fucose metabolism defective in Lec13 cells. Ohyama, C., Smith, P.L., Angata, K., Fukuda, M.N., Lowe, J.B., Fukuda, M. J. Biol. Chem. (1998) [Pubmed]
  20. Crystal structure of a tetrameric GDP-D-mannose 4,6-dehydratase from a bacterial GDP-D-rhamnose biosynthetic pathway. Webb, N.A., Mulichak, A.M., Lam, J.S., Rocchetta, H.L., Garavito, R.M. Protein Sci. (2004) [Pubmed]
  21. Expression, purification and characterization of GDP-D-mannose 4,6-dehydratase from Escherichia coli. Sturla, L., Bisso, A., Zanardi, D., Benatti, U., De Flora, A., Tonetti, M. FEBS Lett. (1997) [Pubmed]
  22. An enzymatic method of analysis for GDP-L-fucose in biological samples, involving high-performance liquid chromatography. Noda, K., Miyoshi, E., Nakahara, S., Ihara, H., Gao, C.X., Honke, K., Yanagidani, S., Sasaki, Y., Kasahara, A., Hori, M., Hayashi, N., Taniguchi, N. Anal. Biochem. (2002) [Pubmed]
  23. Differential expression of genes by tumor cells of a low or a high malignancy phenotype: the case of murine and human Ly-6 proteins. Witz, I.P. J. Cell. Biochem. Suppl. (2000) [Pubmed]
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