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Chemical Compound Review

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

Synonyms: Rhodeose, L-fucose, L-fucopyranose, D-threo-Aldose, Fucose, L-, ...
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Disease relevance of fucose

  • Colonization of germ-free mice with Bacteroides thetaiotaomicron, a component of this flora, restored the fucosylation program, whereas an isogenic strain carrying a transposon insertion that disrupts its ability to use L-fucose as a carbon source did not [1].
  • Combinations of serum protein-bound carbohydrates, particularly L-fucose and sialic acid, and, in addition, CEA, appear to have promise as potential biomarkers for following the course of the disease in patients with metastatic breast cancer [2].
  • Therefore, colitose (3-deoxy-L-fucose), a unique sugar present in the O-antigen of E. coli O111:B4 with structural similarity to L-fucose, is the most probable candidate for a specific ligand of tachylectin-4 [3].
  • Streptomyces sp. 142, isolated from a soil sample, produced alpha-fucosidase when cultured in the presence of L-fucose [4].
  • The bacterium Ralstonia solanacearum, which is distributed worldwide and causes lethal wilt in many agricultural crops, was shown to produce a potent L-fucose-binding lectin, R. solanacearum lectin, a small protein of 90 amino acids with a tandem repeat in its amino acid sequence [5].

High impact information on fucose


Chemical compound and disease context of fucose


Biological context of fucose


Anatomical context of fucose

  • A series of neoglycoproteins, including L-fucose-albumin, were tested as inhibitors of uptake of 125I-labeled beta-glucuronidase into macrophages [16].
  • In vitro, 125I-labeled L-fucose-albumin is taken up into rat or rabbit alveolar macrophages by receptor-mediated pinocytosis [16].
  • The fucosylation defect in LAD II fibroblasts can be corrected by addition of L-fucose to the culture medium [20].
  • Administration of oral L-fucose to the patient produced molecular and clinical responses, as measured by the appearance of selectin ligands, normalization of neutrophil counts, and prevention of infectious recurrence [21].
  • The isolation and characterization of endogenous lectins with specificities for lactose, L-fucose, and D-mannose from U937 controls and TPA-differentiated U937 cells demonstrated marked differences in either the pattern and the distribution of these sugar-specific carbohydrate-binding proteins [22].

Associations of fucose with other chemical compounds

  • Here we investigate the effects of the naturally occurring threonine-linked L-fucose moiety on the structure, dynamics and stability of the proteinase inhibitor PMP-C (Pars intercerebralis major peptide C) [23].
  • Sera from H normal, secretors and nonsecretors (H/-, Se/- and H/-, se/se), as well as from H-deficient secretors (h/h, Se/- or Bombay secretors) contain enzyme(s) for the transfer of L-fucose in the alpha-configuration to the 2-position of suitable beta-D-galactopyranosyl units [24].
  • Reduced motor nerve conduction velocity and Na(+)-K(+)-ATPase activity in rats maintained on L-fucose diet. Reversal by myo-inositol supplementation [18].
  • We substituted different sugars for the glucuronic acids of glycyrrhizin and found the L-fucose derivative to be the most active in vitro and in vivo [25].
  • However, blastocyst formation was inhibited to various extents by high nonphysiological concentrations (50 mM) of D-glucose, D-mannose, L-fucose, D-arabinose, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, alpha-lactose, 25 mM-alpha-melibionic acid and by 2 mg/ml fucoidin, ovine mucin and desialylated ovine mucin [26].

Gene context of fucose

  • The mur1 mutant of Arabidopsis is deficient in L-fucose in the shoot and is rescued by growth in the presence of exogenously supplied L-fucose [27].
  • Based on sequence similarities to a bacterial gene involved in capsule synthesis we have cloned a gene from Arabidopsis, now designated GER1, which encodes a bifunctional 3, 5-epimerase-4-reductase in L-fucose synthesis [28].
  • Upon consideration of the transductional nature of these phage classes, we are proposing that the gene order for the L-fucose utilization system is dar, fucA, (lambda), fucC [29].
  • Stimulation of beta 2m mRNA by Cuprophan was stereospecifically diminished by 5 mM L-fucose [30].
  • Neither CEA nor L-fucose were found to be of value in screening for mammary cancer [31].

Analytical, diagnostic and therapeutic context of fucose


  1. A model of host-microbial interactions in an open mammalian ecosystem. Bry, L., Falk, P.G., Midtvedt, T., Gordon, J.I. Science (1996) [Pubmed]
  2. Serum protein-bound carbohydrates for following the course of disease in patients with metastatic breast carcinoma. Waalkes, T.P., Mrochek, J.E., Dinsmore, S.R., Tormey, D.C. J. Natl. Cancer Inst. (1978) [Pubmed]
  3. A newly identified horseshoe crab lectin with binding specificity to O-antigen of bacterial lipopolysaccharides. Saito, T., Hatada, M., Iwanaga, S., Kawabata, S. J. Biol. Chem. (1997) [Pubmed]
  4. Purification and characterization of alpha-L-fucosidase from Streptomyces species. Sano, M., Hayakawa, K., kato, I. J. Biol. Chem. (1992) [Pubmed]
  5. The fucose-binding lectin from Ralstonia solanacearum. A new type of beta-propeller architecture formed by oligomerization and interacting with fucoside, fucosyllactose, and plant xyloglucan. Kostlánová, N., Mitchell, E.P., Lortat-Jacob, H., Oscarson, S., Lahmann, M., Gilboa-Garber, N., Chambat, G., Wimmerová, M., Imberty, A. J. Biol. Chem. (2005) [Pubmed]
  6. 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]
  7. Inhibition of leukocyte rolling with polysaccharide fucoidin prevents pleocytosis in experimental meningitis in the rabbit. Granert, C., Raud, J., Xie, X., Lindquist, L., Lindbom, L. J. Clin. Invest. (1994) [Pubmed]
  8. Phosphomannosyl receptors may participate in the adhesive interaction between lymphocytes and high endothelial venules. Stoolman, L.M., Tenforde, T.S., Rosen, S.D. J. Cell Biol. (1984) [Pubmed]
  9. Possible role for cell-surface carbohydrate-binding molecules in lymphocyte recirculation. Stoolman, L.M., Rosen, S.D. J. Cell Biol. (1983) [Pubmed]
  10. A molecular sensor that allows a gut commensal to control its nutrient foundation in a competitive ecosystem. Hooper, L.V., Xu, J., Falk, P.G., Midtvedt, T., Gordon, J.I. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  11. Forskolin specifically inhibits the bacterial galactose-H+ transport protein, GalP. Martin, G.E., Seamon, K.B., Brown, F.M., Shanahan, M.F., Roberts, P.E., Henderson, P.J. J. Biol. Chem. (1994) [Pubmed]
  12. Supplemental myo-inositol prevents L-fucose-induced diabetic neuropathy. Sima, A.A., Dunlap, J.A., Davidson, E.P., Wiese, T.J., Lightle, R.L., Greene, D.A., Yorek, M.A. Diabetes (1997) [Pubmed]
  13. L-fucose is a potent inhibitor of myo-inositol transport and metabolism in cultured neuroblastoma cells. Yorek, M.A., Dunlap, J.A., Stefani, M.R., Davidson, E.P. J. Neurochem. (1992) [Pubmed]
  14. Suppression of allergic contact dermatitis by alpha-L-fucose. Hasegawa, S., Baba, T., Hori, Y. J. Invest. Dermatol. (1980) [Pubmed]
  15. Decreased myo-inositol uptake is associated with reduced bradykinin-stimulated phosphatidylinositol synthesis and diacylglycerol content in cultured neuroblastoma cells exposed to L-fucose. Yorek, M.A., Dunlap, J.A., Stefani, M.R., Davidson, E.P., Zhu, X., Eichberg, J. J. Neurochem. (1994) [Pubmed]
  16. L-Fucose-terminated glycoconjugates are recognized by pinocytosis receptors on macrophages. Shepherd, V.L., Lee, Y.C., Schlesinger, P.H., Stahl, P.D. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  17. Lectin-like activities associated with human and murine neoplastic cells. Raz, A., Lotan, R. Cancer Res. (1981) [Pubmed]
  18. Reduced motor nerve conduction velocity and Na(+)-K(+)-ATPase activity in rats maintained on L-fucose diet. Reversal by myo-inositol supplementation. Yorek, M.A., Wiese, T.J., Davidson, E.P., Dunlap, J.A., Stefani, M.R., Conner, C.E., Lattimer, S.A., Kamijo, M., Greene, D.A., Sima, A.A. Diabetes (1993) [Pubmed]
  19. L-fucose is accumulated via a specific transport system in eukaryotic cells. Wiese, T.J., Dunlap, J.A., Yorek, M.A. J. Biol. Chem. (1994) [Pubmed]
  20. Correction of leukocyte adhesion deficiency type II with oral fucose. Marquardt, T., Lühn, K., Srikrishna, G., Freeze, H.H., Harms, E., Vestweber, D. Blood (1999) [Pubmed]
  21. Insights into leukocyte adhesion deficiency type 2 from a novel mutation in the GDP-fucose transporter gene. Hidalgo, A., Ma, S., Peired, A.J., Weiss, L.A., Cunningham-Rundles, C., Frenette, P.S. Blood (2003) [Pubmed]
  22. Alterations in glycosylation and lectin pattern during phorbol ester-induced differentiation of U937 cells. Hass, R., Köhler, L., Rehfeldt, W., Lessmann, V., Müller, W., Resch, K., Goppelt-Struebe, M. Cancer Res. (1990) [Pubmed]
  23. Stabilization of proteins by glycosylation examined by NMR analysis of a fucosylated proteinase inhibitor. Mer, G., Hietter, H., Lefèvre, J.F. Nat. Struct. Biol. (1996) [Pubmed]
  24. The presence of at least two different H-blood-group-related beta-D-gal alpha-2-L-fucosyltransferases in human serum and the genetics of blood group H substances. Le Pendu, J., Cartron, J.P., Lemieux, R.U., Oriol, R. Am. J. Hum. Genet. (1985) [Pubmed]
  25. Sialyl Lewis X mimics derived from a pharmacophore search are selectin inhibitors with anti-inflammatory activity. Rao, B.N., Anderson, M.B., Musser, J.H., Gilbert, J.H., Schaefer, M.E., Foxall, C., Brandley, B.K. J. Biol. Chem. (1994) [Pubmed]
  26. Spreading of blastomeres from eight-cell mouse embryos on lectin-coated beads. Kimber, S.J., Surani, M.A. J. Cell. Sci. (1982) [Pubmed]
  27. 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]
  28. A bifunctional epimerase-reductase acts downstream of the MUR1 gene product and completes the de novo synthesis of GDP-L-fucose in Arabidopsis. Bonin, C.P., Reiter, W.D. Plant J. (2000) [Pubmed]
  29. Analysis of lambda insertions in the fucose utilization region of Escherichia coli K-12: use of lambda fuc and lambda argA transducing bacteriophages to partially order the fucose utilization genes. Skjold, A.C., Ezekiel, D.H. J. Bacteriol. (1982) [Pubmed]
  30. Stimulation of beta 2-microglobulin synthesis in lymphocytes after exposure to Cuprophan dialyzer membranes. Jahn, B., Betz, M., Deppisch, R., Janssen, O., Hänsch, G.M., Ritz, E. Kidney Int. (1991) [Pubmed]
  31. Carcinoembryonic antigen and L-fucose in malignant and benign mammary disease. Wilkinson, E.J., Hause, L.L., Sasse, E.A., Pattillo, R.A., Milbrath, J.R., Lewis, J.D. Am. J. Clin. Pathol. (1980) [Pubmed]
  32. L-fucose metabolism in mammals. Purification of pork liver 2-keto-3-deoxy-L-fuconate:NAD+ oxidoreductase by NAD+-Agarose affinity chromatography. Nwokoro, N.A., Schachter, H. J. Biol. Chem. (1975) [Pubmed]
  33. L-fucose, D-mannose, L-galactose, and their BSA conjugates stimulate macrophage migration. Takata, I., Chida, K., Gordon, M.R., Myrvik, Q.N., Ricardo, M.J., Kucera, L.S. J. Leukoc. Biol. (1987) [Pubmed]
  34. Conformational separation of monosaccharides of glycoproteins labeled with 2-aminoacrydone using microchip electrophoresis. Maeda, E., Hirano, K., Baba, Y., Nagata, H., Tabuchi, M. Electrophoresis (2006) [Pubmed]
  35. L-fucose labeling of brain tumors in rats. Harsh, G.R., Nishimura, R.N., Dwyer, B.E., Levin, V.A. Exp. Neurol. (1986) [Pubmed]
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