2.02012-05-31 10:22:56 -06002015-09-13 12:56:06 -0600ECMDB00174M2MDB000072L-FucoseFucose is a hexose sugar with the chemical formula C6H12O5. Alpha1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. (Wikipedia)α-L-fucopyranose(-)-Fucose(-)-L-Fucose6-Deoxy-b-galactose6-Deoxy-beta-galactose6-Deoxy-D-galactopyranose6-Deoxy-delta-galactopyranose6-Deoxy-L-b-galactose6-Deoxy-L-beta-galactose6-Deoxy-L-galactopyranose6-Deoxy-L-galactose6-Deoxy-L-β-galactose6-Deoxy-β-galactose6-Deoxy-δ-galactopyranose6-Desoxygalactose6-Methyloxane-2,3,4,5-tetrol6-Methyltetrahydropyran-2,3,4,5-tetraola-L-FucopyranoseAlpha-L-FucopyranoseD-Threo-AldoseFucoseIsodulcitL-(-)-FucoseL-FucopyranoseL-FucoseL-GalactomethyloseRhodeoseα-L-FucopyranoseC6H12O5164.1565164.068473494(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrolL-fucose2438-80-4C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1OInChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1SHZGCJCMOBCMKK-DHVFOXMCSA-NSolidCytosolExtra-organismPeriplasmmelting_point140 oClogp-1.9ChemAxonpka_strongest_acidic11.3ChemAxonpka_strongest_basic-3.6ChemAxoniupac(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrolChemAxonaverage_mass164.1565ChemAxonmono_mass164.068473494ChemAxonsmilesC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1OChemAxonformulaC6H12O5ChemAxoninchiInChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1ChemAxoninchikeySHZGCJCMOBCMKK-DHVFOXMCSA-NChemAxonpolar_surface_area90.15ChemAxonrefractivity34.38ChemAxonpolarizability15.35ChemAxonrotatable_bond_count0ChemAxonacceptor_count5ChemAxondonor_count4ChemAxonphysiological_charge0ChemAxonformal_charge0ChemAxonFructose and mannose metabolismec00051Amino sugar and nucleotide sugar metabolismec00520Microbial metabolism in diverse environmentsec01120Specdb::CMs9738Specdb::CMs31911Specdb::CMs31912Specdb::CMs37337Specdb::CMs99539Specdb::CMs99540Specdb::NmrOneD1139Specdb::NmrOneD1191Specdb::NmrOneD166520Specdb::MsMs274Specdb::MsMs275Specdb::MsMs276Specdb::MsMs287509Specdb::MsMs287510Specdb::MsMs287511Specdb::MsMs326374Specdb::MsMs326375Specdb::MsMs326376Specdb::NmrTwoD982Specdb::NmrTwoD1186HMDB001741710616190C0101918287CPD-10329AFLL-FucoseKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811.7762816Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89.3757018Condaminet B, Peguet-Navarro J, Stahl PD, Dalbiez-Gauthier C, Schmitt D, Berthier-Vergnes O: Human epidermal Langerhans cells express the mannose-fucose binding receptor. Eur J Immunol. 1998 Nov;28(11):3541-51.9842897Havenaar EC, Hoff RC, van den Eijnden DH, van Dijk W: Sialyl Lewis(x) epitopes do not occur on acute phase proteins in mice: relationship to the absence of alpha3-fucosyltransferase in the liver. Glycoconj J. 1998 Apr;15(4):389-95.9613826Roelfzema H, van Erp PE: Studies on the plasma membrane of normal and psoriatic keratinocytes. 6. Cell surface and shed glycoproteins. J Invest Dermatol. 1983 Jan;80(1):24-6.6184420Wiese TJ, Dunlap JA, Yorek MA: Effect of L-fucose and D-glucose concentration on L-fucoprotein metabolism in human Hep G2 cells and changes in fucosyltransferase and alpha-L-fucosidase activity in liver of diabetic rats. Biochim Biophys Acta. 1997 Apr 17;1335(1-2):61-72.9133643Isnard N, Fodil-Bourahla I, Robert AM, Robert L: Pharmacology of skin aging. Stimulation of glycosaminoglycan biosynthesis by L-fucose and fucose-rich polysaccharides, effect of in vitro aging of fibroblasts. Biomed Pharmacother. 2004 Apr;58(3):202-4.15082343Rizzi M, Tonetti M, Vigevani P, Sturla L, Bisso A, Flora AD, Bordo D, Bolognesi M: 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. Structure. 1998 Nov 15;6(11):1453-65.9817848Gheri G, Sgambati E, Thyrion GD, Vichi D, Orlandini GE: The oligosaccharidic content of the glycoconjugates of the prepubertal descended and undescended testis: lectin histochemical study. Ital J Anat Embryol. 2004 Apr-Jun;109(2):69-84.15481156Fediv OI, Kolomoiets' MIu: [Role of cytokines in the metabolism of the extracellular matrix carbohydrate-protein components in patients of various ages with gastroduodenal ulcer] Lik Sprava. 2001 Jul-Aug;(4):181-2.11692712Hutchinson WL, Du MQ, Johnson PJ, Williams R: Fucosyltransferases: differential plasma and tissue alterations in hepatocellular carcinoma and cirrhosis. Hepatology. 1991 Apr;13(4):683-8.1849114Fleischer M, Przondo-Mordarska A: [Adhesins of Acinetobacter strains] Med Dosw Mikrobiol. 1998;50(3-4):229-37.10222738Gohlke M, Baude G, Nuck R, Grunow D, Kannicht C, Bringmann P, Donner P, Reutter W: O-linked L-fucose is present in Desmodus rotundus salivary plasminogen activator. J Biol Chem. 1996 Mar 29;271(13):7381-6.8631761Chien CM, Cheng JL, Chang WT, Tien MH, Tsao CM, Chang YH, Chang HY, Hsieh JF, Wong CH, Chen ST: Polysaccharides of Ganoderma lucidum alter cell immunophenotypic expression and enhance CD56+ NK-cell cytotoxicity in cord blood. Bioorg Med Chem. 2004 Nov 1;12(21):5603-9.15465338Hanisch FG, Heimbuchel G, Baldus SE, Uhlenbruck G, Schmits R, Pfreundschuh M, Schwonzen M, Vierbuchen M, Bara J, Peter-Katalinic J: Monoclonal antibody FW6 defines an epitope on alpha 3/4-monofucosylated polylactosaminoglycans expressed by fetal and colon carcinoma-associated mucins. Cancer Res. 1993 Sep 15;53(18):4367-75.8364932Tonetti M, Sturla L, Bisso A, Zanardi D, Benatti U, De Flora A: The metabolism of 6-deoxyhexoses in bacterial and animal cells. Biochimie. 1998 Nov;80(11):923-31.9893952Sato T, Sato M, Kiyohara K, Sogabe M, Shikanai T, Kikuchi N, Togayachi A, Ishida H, Ito H, Kameyama A, Gotoh M, Narimatsu H: Molecular cloning and characterization of a novel human {beta}1,3-glucosyltransferase, which is localized at the endoplasmic reticulum and glucosylates O-linked fucosylglycan on thrombospondin type 1 repeat domain. Glycobiology. 2006 Dec;16(12):1194-1206. Epub 2006 Aug 9.16899492Coyne MJ, Reinap B, Lee MM, Comstock LE: Human symbionts use a host-like pathway for surface fucosylation. Science. 2005 Mar 18;307(5716):1778-81.15774760Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63.16086588Bathi RJ, Nandimath K, Kannan N, Shetty P: Evaluation of glycoproteins as prognosticators in head and neck malignancy. Indian J Dent Res. 2001 Apr-Jun;12(2):93-9.11665403Sakai T, Yamamoto K, Yokota H, Hakozaki-Usui K, Hino F, Kato I: Rapid, simple enzymatic assay of free L-fucose in serum and urine, and its use as a marker for cancer, cirrhosis, and gastric ulcers. Clin Chem. 1990 Mar;36(3):474-6.2311216Yamauchi M, Kimura K, Maezawa Y, Ohata M, Mizuhara Y, Hirakawa J, Nakajima H, Toda G: Urinary level of L-fucose as a marker of alcoholic liver disease. Alcohol Clin Exp Res. 1993 Apr;17(2):268-71.8488966Xu, Zuhong; Zhao, Zengqin; Zhang, Quanbin; Niu, Xizhen; Zhang, Hong; Li, Zhien. Method for preparing L-fucose from laminaria japonica. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp. http://hmdb.ca/system/metabolites/msds/000/000/123/original/HMDB00174.pdf?1358462447L-fucose-proton symporterP11551FUCP_ECOLIfucPhttp://ecmdb.ca/proteins/P11551.xmlL-fucose isomeraseP69922FUCI_ECOLIfucIhttp://ecmdb.ca/proteins/P69922.xmlL-fucose-proton symporterP11551FUCP_ECOLIfucPhttp://ecmdb.ca/proteins/P11551.xmlSugar efflux transporter CP31436SETC_ECOLIsetChttp://ecmdb.ca/proteins/P31436.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlL-Fucose <> L-FuculoseR03163L-Fucose <> beta-L-fucoseRXN0-5298L-Fucose > L-Fuculose