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Chemical Compound Review

Gdp fucose     [(2R,3S,4R,5R)-5-(2-amino-6- oxo-3H-purin-9...

Synonyms: AC1L1DD4, 15839-70-0, Guanosine diphosphofucose, guanosine diphosphate fucose
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Disease relevance of Gdp fucose


Psychiatry related information on Gdp fucose


High impact information on Gdp fucose


Biological context of Gdp fucose

  • We report here that mice with an induced null mutation in the FX locus, which encodes an enzyme in the de novo pathway for GDP-fucose synthesis, exhibit a virtually complete deficiency of cellular fucosylation, and variable frequency of intrauterine demise determined by parental FX genotype [11].
  • While both enzymatic activities exhibit similar affinities for a synthetic alpha-(1-3) acceptor and GDP-fucose, they differ with respect to divalent cation requirements, N-ethylmaleimide inhibition, and glycoprotein substrate specificity [12].
  • GDP-fucose synthetase from E. coli is a novel dual function enzyme in that it catalyzes epimerizations and a reduction reaction at the same active site [1].
  • We have described previously a gene transfer system for the isolation of human DNA sequences that determine expression of a mammalian GDP-fucose: beta-D-galactoside-2-alpha-L-fucosyltransferase (alpha-(1,2)-fucosyltransferase) (Ernst, L. K., Rajan, V. P., Larsen, R. D., Ruff, M. M., and Lowe, J. B. (1989) J. Biol. Chem. 264, 3436-3447) [13].
  • In our patient the saturable high affinity import of GDP-fucose was deficient, while import of UDP-galactose and the activity of GDPase, which generates the nucleoside phosphate required for antiport of GDP-fucose, were normal [2].

Anatomical context of Gdp fucose

  • A defect in GDP-fucose transport into the lumen of the Golgi apparatus has been recently identified in a patient affected by leukocyte adhesion deficiency type II syndrome (Lubke, T., Marquardt, T., von Figura, K., and Korner, C. (1999) J. Biol. Chem. 274, 25986-25989) [14].
  • Pea microsomes contain an alpha-fucosyltransferase that incorporates fucose from GDP-fucose into xyloglucan, adding it preferentially to the 2-O-position of the galactosyl residue closest to the reducing end of the repeating subunit [15].
  • Both mutant and normal cytosols are also able to alpha-fucosylate a type 1 glycolipid substrate (8-methoxycarbonyloctyl-Gal beta 1-3 beta GlcNAc), but not related substrates, with Km values for the type 1 glycolipid of 0.99 mM and for GDP-fucose of 1.6 microM [16].
  • The enzyme that adds O-fucose to epidermal growth factor-like repeats, GDP-fucose protein O-fucosyltransferase (O-FucT-1), was purified previously from Chinese hamster ovary (CHO) cells [17].
  • We have found that a readily accessible, partially purified Le-FucT from human milk, which normally uses GDP-fucose (a 6-deoxy sugar) as the donor for the transfer of a single fucose residue, will also transfer a fucose residue substituted on C-6 by a very large sterically demanding structure, in this instance, a synthetic blood group antigen [18].

Associations of Gdp fucose with other chemical compounds


Gene context of Gdp fucose


Analytical, diagnostic and therapeutic context of Gdp fucose


  1. Stereochemical course and steady state mechanism of the reaction catalyzed by the GDP-fucose synthetase from Escherichia coli. Menon, S., Stahl, M., Kumar, R., Xu, G.Y., Sullivan, F. J. Biol. Chem. (1999) [Pubmed]
  2. A new type of carbohydrate-deficient glycoprotein syndrome due to a decreased import of GDP-fucose into the golgi. Lübke, T., Marquardt, T., von Figura, K., Körner, C. J. Biol. Chem. (1999) [Pubmed]
  3. Mutation in GDP-fucose synthesis genes of Sinorhizobium fredii alters Nod factors and significantly decreases competitiveness to nodulate soybeans. Lamrabet, Y., Bellogín, R.A., Cubo, T., Espuny, R., Gil, A., Krishnan, H.B., Megias, M., Ollero, F.J., Pueppke, S.G., Ruiz-Sainz, J.E., Spaink, H.P., Tejero-Mateo, P., Thomas-Oates, J., Vinardell, J.M. Mol. Plant Microbe Interact. (1999) [Pubmed]
  4. The nodulation gene nolK of Azorhizobium caulinodans is involved in the formation of GDP-fucose from GDP-mannose. Mergaert, P., Van Montagu, M., Holsters, M. FEBS Lett. (1997) [Pubmed]
  5. The chemical carcinogen-induced enzyme, GDP-fucose: GM1 alpha 1----2 fucosyltransferase in rat liver and hepatoma: modulation by and association with phospholipids. Holmes, E.H., Hakomori, S. J. Biochem. (1987) [Pubmed]
  6. The use of human milk fucosyltransferase in the synthesis of tumor-associated trimeric X determinants. de Vries, T., Norberg, T., Lönn, H., Van den Eijnden, D.H. Eur. J. Biochem. (1993) [Pubmed]
  7. Complementation cloning identifies CDG-IIc, a new type of congenital disorders of glycosylation, as a GDP-fucose transporter deficiency. Lübke, T., Marquardt, T., Etzioni, A., Hartmann, E., von Figura, K., Körner, C. Nat. Genet. (2001) [Pubmed]
  8. The gene defective in leukocyte adhesion deficiency II encodes a putative GDP-fucose transporter. Lühn, K., Wild, M.K., Eckhardt, M., Gerardy-Schahn, R., Vestweber, D. Nat. Genet. (2001) [Pubmed]
  9. Leukocyte Adhesion Deficiency Type II is a generalized defect of de novo GDP-fucose biosynthesis. Endothelial cell fucosylation is not required for neutrophil rolling on human nonlymphoid endothelium. Karsan, A., Cornejo, C.J., Winn, R.K., Schwartz, B.R., Way, W., Lannir, N., Gershoni-Baruch, R., Etzioni, A., Ochs, H.D., Harlan, J.M. J. Clin. Invest. (1998) [Pubmed]
  10. Fucosyltransferase activity in metastasizing and nonmetastasizing rat mammary carcinomas. Chatterjee, S.K., Kim, U. J. Natl. Cancer Inst. (1978) [Pubmed]
  11. Conditional control of selectin ligand expression and global fucosylation events in mice with a targeted mutation at the FX locus. Smith, P.L., Myers, J.T., Rogers, C.E., Zhou, L., Petryniak, B., Becker, D.J., Homeister, J.W., Lowe, J.B. J. Cell Biol. (2002) [Pubmed]
  12. Identification and characterization of two distinct alpha-(1-3)-L-fucosyltransferase activities in human colon carcinoma. Stroup, G.B., Anumula, K.R., Kline, T.F., Caltabiano, M.M. Cancer Res. (1990) [Pubmed]
  13. A cloned human DNA restriction fragment determines expression of a GDP-L-fucose: beta-D-galactoside 2-alpha-L-fucosyltransferase in transfected cells. Evidence for isolation and transfer of the human H blood group locus. Rajan, V.P., Larsen, R.D., Ajmera, S., Ernst, L.K., Lowe, J.B. J. Biol. Chem. (1989) [Pubmed]
  14. Reconstitution, identification, and purification of the rat liver golgi membrane GDP-fucose transporter. Puglielli, L., Hirschberg, C.B. J. Biol. Chem. (1999) [Pubmed]
  15. Biochemical characterization and molecular cloning of an alpha-1,2-fucosyltransferase that catalyzes the last step of cell wall xyloglucan biosynthesis in pea. Faik, A., Bar-Peled, M., DeRocher, A.E., Zeng, W., Perrin, R.M., Wilkerson, C., Raikhel, N.V., Keegstra, K. J. Biol. Chem. (2000) [Pubmed]
  16. Characterization of a cytosolic fucosylation pathway in Dictyostelium. Gonzalez-Yanes, B., Cicero, J.M., Brown, R.D., West, C.M. J. Biol. Chem. (1992) [Pubmed]
  17. Modification of epidermal growth factor-like repeats with O-fucose. Molecular cloning and expression of a novel GDP-fucose protein O-fucosyltransferase. Wang, Y., Shao, L., Shi, S., Harris, R.J., Spellman, M.W., Stanley, P., Haltiwanger, R.S. J. Biol. Chem. (2001) [Pubmed]
  18. Enzymatic transfer of a preassembled trisaccharide antigen to cell surfaces using a fucosyltransferase. Srivastava, G., Kaur, K.J., Hindsgaul, O., Palcic, M.M. J. Biol. Chem. (1992) [Pubmed]
  19. Molecular cloning of human GDP-mannose 4,6-dehydratase and reconstitution of GDP-fucose biosynthesis in vitro. Sullivan, F.X., Kumar, R., Kriz, R., Stahl, M., Xu, G.Y., Rouse, J., Chang, X.J., Boodhoo, A., Potvin, B., Cumming, D.A. J. Biol. Chem. (1998) [Pubmed]
  20. Effect of atractylosides, palmitoyl coenzyme A, and anion transport inhibitors on translocation of nucleotide sugars and nucleotide sulfate into Golgi vesicles. Capasso, J.M., Hirschberg, C.B. J. Biol. Chem. (1984) [Pubmed]
  21. Plasma fucosyltransferase activity in patients with hepatocellular carcinoma, with special reference to correlation with fucosylated species of alpha-fetoprotein. Mita, Y., Aoyagi, Y., Suda, T., Asakura, H. J. Hepatol. (2000) [Pubmed]
  22. AtUTr2 is an Arabidopsis thaliana nucleotide sugar transporter located in the Golgi apparatus capable of transporting UDP-galactose. Norambuena, L., Nilo, R., Handford, M., Reyes, F., Marchant, L., Meisel, L., Orellana, A. Planta (2005) [Pubmed]
  23. Interaction of GDP-4-keto-6-deoxymannose-3,5-epimerase-4-reductase with GDP-mannose-4,6-dehydratase stabilizes the enzyme activity for formation of GDP-fucose from GDP-mannose. Nakayama, K., Maeda, Y., Jigami, Y. Glycobiology (2003) [Pubmed]
  24. Identification and molecular cloning of a functional GDP-fucose transporter in Drosophila melanogaster. Lühn, K., Laskowska, A., Pielage, J., Klämbt, C., Ipe, U., Vestweber, D., Wild, M.K. Exp. Cell Res. (2004) [Pubmed]
  25. Acceptor specificity of different length constructs of human recombinant alpha 1,3/4-fucosyltransferases. Replacement of the stem region and the transmembrane domain of fucosyltransferase V by protein A results in an enzyme with GDP-fucose hydrolyzing activity. de Vries, T., Srnka, C.A., Palcic, M.M., Swiedler, S.J., van den Eijnden, D.H., Macher, B.A. J. Biol. Chem. (1995) [Pubmed]
  26. Sequence of Escherichia coli O128 antigen biosynthesis cluster and functional identification of an alpha-1,2-fucosyltransferase. Shao, J., Li, M., Jia, Q., Lu, Y., Wang, P.G. FEBS Lett. (2003) [Pubmed]
  27. Evaluation of two plasma fucosyltransferases as marker enzymes in non-Hodgkin's lymphoma. Khilanani, P., Chou, T.H., Ratanatharathorn, V., Kessel, D. Cancer (1978) [Pubmed]
  28. Inhibition kinetics of carba- and C-fucosyl analogues of GDP-fucose against fucosyltransferase V: implication for the reaction mechanism. Norris, A.J., Whitelegge, J.P., Strouse, M.J., Faull, K.F., Toyokuni, T. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
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