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Chemical Compound Review

fucose     (2R,3S,4R,5S,6S)-6- methyloxane-2,3,4,5-tetrol

Synonyms: alpha-L-Fuc, alpha-L-Fucp, ALPHA-L-FUCOSE, SureCN348315, CHEBI:28349, ...
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Disease relevance of fucose


Psychiatry related information on fucose

  • If the electroshock was delayed by 10 min, the chicks showed recall for the task and fucose incorporation was increased by comparison with untrained but shocked or trained and immediate-shocked birds [6].
  • Developmental abnormalities (growth and mental retardation) constitute a prominent feature of LAD II and may be attributed to a general defect found in fucose metabolism in LAD II [7].

High impact information on fucose

  • Notch and its ligands are modified by a protein O-fucosyltransferase (OFUT1) that attaches fucose to a Serine or Threonine within EGF domains [8].
  • Using a fucose-specific, lectin-staining procedure for detection of fucosylated glycoproteins and a retroviral cDNA library, we isolated a cDNA complementing the fucosylation defect in the patient's fibroblasts [9].
  • Drosophila and mammalian Fringe proteins possess a fucose-specific beta1,3 N-acetylglucosaminyltransferase activity that initiates elongation of O-linked fucose residues attached to epidermal growth factor-like sequence repeats of Notch [10].
  • The survival of mur1 plants challenged the hypothesis that fucose is a required component of biologically active oligosaccharides derived from cell wall xyloglucan [11].
  • The crucial control oligosaccharides, sialyl lactosamines lacking fucose but being otherwise similar to the members of sLex family, had no effect on lymphocyte binding [12].

Chemical compound and disease context of fucose


Biological context of fucose


Anatomical context of fucose

  • Further evidence for the essential role of macrophage surface fucose was obtained by demonstrating that pretreatment of macrophages with either fucosidase or gorse lectin, a fucose-binding lectin, strikingly disabled the cells from responding to the lymphokine [18].
  • Labeling with fucose did not appear to result in any differences, thus suggesting that the glycopeptides characertistic of trophoblast contained glucosamine-derived metabolic products, including sialic acid, but excluding fucose [23].
  • These findings suggest that fucosylation of nonlymphoid endothelial cells does not play a major role in neutrophil rolling and that fucose is not a critical moiety on the L-selectin ligand(s) on endothelial cells of the systemic vasculature [24].
  • LAD II HUVEC lacking fucosylated glycoproteins supported leukocyte rolling to a similar degree as normal HUVEC or LAD II cells that were fucose-fed [24].
  • At low shear rates, an L-selectin antibody inhibited neutrophil rolling to a similar degree whether the LAD II cells had been fucose-fed or not [24].

Associations of fucose with other chemical compounds

  • The increased synthesis of C2, which appeared to be mediated by a lymphokine, was partially inhibited specifically by 0.025 M alpha-L(-) fucose, a sugar which has previously been shown in inhibit the response of macrophages to migration inhibitory factor [25].
  • The fact that the binding of alglucerase by macrophages was mediated principally by a receptor distinct from the classical mannose receptor that binds mannose-BSA was confirmed by differential inhibitors, viz., alpha-methyl-glucoside, fucose, and mannose-BSA, and by its independence on Ca2+ [26].
  • Because fucose is incorporated into secretory proteins almost exclusively in the Golgi complex, fucose-labeled proteins accumulated in the livers of the ethanol-treated rats mainly in the Golgi apparatus, with the remainder located in the cytosol [27].
  • Axons separated from cell bodies showed no incorporation of label from leucine or fucose, but did exhibit incorporation of glucosamine [28].
  • Contingent restoration of leukocyte and endothelial selectin ligand expression, general cellular fucosylation, and normal postnatal physiology is achieved by modulating dietary fucose to supply a salvage pathway for GDP-fucose synthesis [3].

Gene context of fucose

  • To investigate physiological functions of the core fucose, we generated alpha1,6-fucosyltransferase (Fut8)-null mice and found that disruption of Fut8 induces severe growth retardation and death during postnatal development [20].
  • Further, we show that neurotic is required for Fringe activity, which encodes a fucose-specific beta1, 3 N-acetylglucosaminyltransferase, previously shown to modulate Notch receptor activity [29].
  • By contrast, MCF-7, MDA-MB231, and ZR75-1 cells glycosylate the MUC1 repeat peptide preferentially with core 2-based glycans terminating mostly with alpha 3-linked sialic acid (MDA-MB231, ZR75-1) or alpha 2/3-linked fucose (MCF-7) [30].
  • We have found that the EGF-CFC family member human Cripto-1 (CR) is modified with fucose and through a combination of peptide mapping, mass spectrometry, and sequence analysis localized the site of attachment to Thr-88 [31].
  • Treatment of NCAM-Fc with Charonia lampas alpha-fucosidase, which is able to cleave alpha1,6-linked fucose, clearly reduced the polysialylation of NCAM-Fc by ST8Sia II [32].

Analytical, diagnostic and therapeutic context of fucose

  • Incorporation of fucose and galactose into purified carcinoembryonic antigen (CEA), used as an exogenous acceptor by colon glycosyltransferases, was demonstrated by immunoprecipitation with rabbit antiserum to human CEA [33].
  • Seven rounds of DNA shuffling and colony screening on chromogenic fucose substrates were performed, using 10,000 colonies per round [34].
  • Surface glycopeptides of the various myeloid cells were investigated by gel filtration analysis after metabolic labeling with radioactive fucose or after external labeling with periodate-borotritide under mild conditions [35].
  • Analysis of this material was accomplished by amino acid analyzer and by gas-liquid chromatography; fucose, glucosamine, and aspartic acid in molar ratios of approximately 1.0:1.0:1.0 were observed [36].
  • Further, we describe the identification by matrix-assisted laser desorption-ionization time-of-flight mass spectrometry and high performance liquid chromatography of two Drosophila N-glycans that, as already detected in other insects, carry both alpha1,3- and alpha1,6-linked fucose residues on the proximal core GlcNAc [37].


  1. NGF stimulates incorporation of fucose or glucosamine into an external glycoprotein in cultured rat PC12 pheochromocytoma cells. McGuire, J.C., Greene, L.A., Furano, A.V. Cell (1978) [Pubmed]
  2. The carbohydrate composition of mucin in colonic cancer. Boland, C.R., Deshmukh, G.D. Gastroenterology (1990) [Pubmed]
  3. 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]
  4. A route for fructose utilization by Escherichia coli involving the fucose regulon. Kornberg, H., Lourenco, C. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  5. Biosynthesis in vitro of fucose-containing glycosphingolipids in human neuroblastoma IMR-32 cells. Presper, K.A., Basu, M., Basu, S. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  6. Training increases [3H]fucose incorporation in chick brain only if followed by memory storage. Rose, S.P., Harding, S. Neuroscience (1984) [Pubmed]
  7. Adhesion molecule deficiencies and their clinical significance. Etzioni, A. Cell Adhes. Commun. (1994) [Pubmed]
  8. Regulation of notch signaling by o-linked fucose. Okajima, T., Irvine, K.D. Cell (2002) [Pubmed]
  9. 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]
  10. Fringe is a glycosyltransferase that modifies Notch. Moloney, D.J., Panin, V.M., Johnston, S.H., Chen, J., Shao, L., Wilson, R., Wang, Y., Stanley, P., Irvine, K.D., Haltiwanger, R.S., Vogt, T.F. Nature (2000) [Pubmed]
  11. Substitution of L-fucose by L-galactose in cell walls of Arabidopsis mur1. Zablackis, E., York, W.S., Pauly, M., Hantus, S., Reiter, W.D., Chapple, C.C., Albersheim, P., Darvill, A. Science (1996) [Pubmed]
  12. De novo expression of endothelial sialyl Lewis(a) and sialyl Lewis(x) during cardiac transplant rejection: superior capacity of a tetravalent sialyl Lewis(x) oligosaccharide in inhibiting L-selectin-dependent lymphocyte adhesion. Turunen, J.P., Majuri, M.L., Seppo, A., Tiisala, S., Paavonen, T., Miyasaka, M., Lemström, K., Penttilä, L., Renkonen, O., Renkonen, R. J. Exp. Med. (1995) [Pubmed]
  13. Urinary glycopeptides of fucosidosis. Yamashita, K., Tachibana, Y., Takada, S., Matsuda, I., Arashima, S., Kobata, A. J. Biol. Chem. (1979) [Pubmed]
  14. Structural characterization of the O-antigenic polysaccharide of the lipopolysaccharide from Rhizobium etli strain CE3. A unique O-acetylated glycan of discrete size, containing 3-O-methyl-6-deoxy-L-talose and 2,3,4-tri-O-,methyl-l fucose. Forsberg, L.S., Bhat, U.R., Carlson, R.W. J. Biol. Chem. (2000) [Pubmed]
  15. C-terminal amino acids of Helicobacter pylori alpha1,3/4 fucosyltransferases determine type I and type II transfer. Ma, B., Wang, G., Palcic, M.M., Hazes, B., Taylor, D.E. J. Biol. Chem. (2003) [Pubmed]
  16. 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]
  17. Characterization of the O-polysaccharide structure of lipopolysaccharide from Actinobacillus actinomycetemcomitans serotype b. Perry, M.B., MacLean, L.L., Gmür, R., Wilson, M.E. Infect. Immun. (1996) [Pubmed]
  18. Augmentation of macrophage complement receptor function in vitro. IV. The lymphokine that activates macrophage C3 receptors for phagocytosis binds to a fucose-bearing glycoprotein on the macrophage plasma membrane. Griffin, F.M., Mullinax, P.J. J. Exp. Med. (1984) [Pubmed]
  19. Polar zipper sequence in the high-affinity hemoglobin of Ascaris suum: amino acid sequence and structural interpretation. De Baere, I., Liu, L., Moens, L., Van Beeumen, J., Gielens, C., Richelle, J., Trotman, C., Finch, J., Gerstein, M., Perutz, M. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  20. Dysregulation of TGF-beta1 receptor activation leads to abnormal lung development and emphysema-like phenotype in core fucose-deficient mice. Wang, X., Inoue, S., Gu, J., Miyoshi, E., Noda, K., Li, W., Mizuno-Horikawa, Y., Nakano, M., Asahi, M., Takahashi, M., Uozumi, N., Ihara, S., Lee, S.H., Ikeda, Y., Yamaguchi, Y., Aze, Y., Tomiyama, Y., Fujii, J., Suzuki, K., Kondo, A., Shapiro, S.D., Lopez-Otin, C., Kuwaki, T., Okabe, M., Honke, K., Taniguchi, N. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  21. A novel fucose recognition fold involved in innate immunity. Bianchet, M.A., Odom, E.W., Vasta, G.R., Amzel, L.M. Nat. Struct. Biol. (2002) [Pubmed]
  22. Defucosylated chimeric anti-CC chemokine receptor 4 IgG1 with enhanced antibody-dependent cellular cytotoxicity shows potent therapeutic activity to T-cell leukemia and lymphoma. Niwa, R., Shoji-Hosaka, E., Sakurada, M., Shinkawa, T., Uchida, K., Nakamura, K., Matsushima, K., Ueda, R., Hanai, N., Shitara, K. Cancer Res. (2004) [Pubmed]
  23. Increased sialylation of surface glycopeptides of human trophoblast compared with fetal cells from the same conceptus. Whyte, A., Loke, Y.W. J. Exp. Med. (1978) [Pubmed]
  24. 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]
  25. Production of the second component of complement by human monocytes: stimulation by antigen-activated lymphocytes or lymphokines. Littman, B.H., Ruddy, S. J. Exp. Med. (1977) [Pubmed]
  26. Binding, internalization, and degradation of mannose-terminated glucocerebrosidase by macrophages. Sato, Y., Beutler, E. J. Clin. Invest. (1993) [Pubmed]
  27. Subcellular location of secretory proteins retained in the liver during the ethanol-induced inhibition of hepatic protein secretion in the rat. Volentine, G.D., Tuma, D.J., Sorrell, M.F. Gastroenterology (1986) [Pubmed]
  28. Compositional analysis of growing axons from rat sympathetic neurons. Estridge, M., Bunge, R. J. Cell Biol. (1978) [Pubmed]
  29. neurotic, a novel maternal neurogenic gene, encodes an O-fucosyltransferase that is essential for Notch-Delta interactions. Sasamura, T., Sasaki, N., Miyashita, F., Nakao, S., Ishikawa, H.O., Ito, M., Kitagawa, M., Harigaya, K., Spana, E., Bilder, D., Perrimon, N., Matsuno, K. Development (2003) [Pubmed]
  30. Recombinant MUC1 probe authentically reflects cell-specific O-glycosylation profiles of endogenous breast cancer mucin. High density and prevalent core 2-based glycosylation. Müller, S., Hanisch, F.G. J. Biol. Chem. (2002) [Pubmed]
  31. Fucosylation of Cripto is required for its ability to facilitate nodal signaling. Schiffer, S.G., Foley, S., Kaffashan, A., Hronowski, X., Zichittella, A.E., Yeo, C.Y., Miatkowski, K., Adkins, H.B., Damon, B., Whitman, M., Salomon, D., Sanicola, M., Williams, K.P. J. Biol. Chem. (2001) [Pubmed]
  32. Characterization of mouse ST8Sia II (STX) as a neural cell adhesion molecule-specific polysialic acid synthase. Requirement of core alpha1,6-linked fucose and a polypeptide chain for polysialylation. Kojima, N., Tachida, Y., Yoshida, Y., Tsuji, S. J. Biol. Chem. (1996) [Pubmed]
  33. Alterations in glycosyltransferase activity in human colon cancer. LaMont, J.T., Isselbacher, K.J. J. Natl. Cancer Inst. (1975) [Pubmed]
  34. Directed evolution of a fucosidase from a galactosidase by DNA shuffling and screening. Zhang, J.H., Dawes, G., Stemmer, W.P. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  35. Transient versus permanent expression of cancer-related glycopeptides on normal versus leukemic myeloid cells coinciding with marrow egress. van Beek, W., Tulp, A., Bolscher, J., Blanken, G., Roozendaal, K., Egbers, M. Blood (1984) [Pubmed]
  36. Characterization of an amino acid fucoside of normal and SV40-transformed human embryonic lung cells. Morton, P.A., Klinger, M.M., Steiner, S.M. Cancer Res. (1982) [Pubmed]
  37. Identification of core alpha 1,3-fucosylated glycans and cloning of the requisite fucosyltransferase cDNA from Drosophila melanogaster. Potential basis of the neural anti-horseadish peroxidase epitope. Fabini, G., Freilinger, A., Altmann, F., Wilson, I.B. J. Biol. Chem. (2001) [Pubmed]
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