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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:48 UTC
NP-MRD IDNP0001115
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Fucose
DescriptionFucose is a hexose deoxy sugar with the chemical formula C6H12O5. L-fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental sub-unit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: The lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. 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. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers (PMID: 2311216 ) (PMID: 8488966 ). Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics
Structure
Thumb
Synonyms
ValueSource
(-)-L-FucoseChEBI
(3S,4R,5R,6S)-6-Methyloxane-2,3,4,5-tetrolChEBI
(3S,4R,5R,6S)-6-Methyltetrahydropyran-2,3,4,5-tetrolChEBI
(3S,4R,5S,6S)-6-Methyloxane-2,3,4,5-tetrolChEBI
6-Deoxy-L-galactoseChEBI
WURCS=2.0/1,1,0/[a1221m-1x_1-5]/1/ChEBI
(-)-FucoseHMDB
6-Deoxy-L-galactopyranoseHMDB
6-DesoxygalactoseHMDB
6-Methyloxane-2,3,4,5-tetrolHMDB
6-Methyltetrahydropyran-2,3,4,5-tetraolHMDB
FucoseHMDB, MeSH
IsodulcitHMDB
L-(-)-FucoseHMDB
L-FucopyranoseHMDB
L-GalactomethyloseHMDB
RhodeoseHMDB
alpha FucoseMeSH, HMDB
alpha-FucoseMeSH, HMDB
DeoxygalactoseMeSH, HMDB
Chemical FormulaC6H12O5
Average Mass164.1565 Da
Monoisotopic Mass164.06847 Da
IUPAC Name(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional NameL-fucose
CAS Registry Number2438-80-4
SMILES
C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1
InChI KeySHZGCJCMOBCMKK-DHVFOXMCSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Averrhoa carambolaKNApSAcK Database
Prunus aviumKNApSAcK Database
Solanum lycopersicum L.KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling Point323.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility985 mg/mLNot Available
LogP-0.340 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility827 g/LALOGPS
logP-1.9ChemAxon
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020543
KNApSAcK IDC00035100
Chemspider ID16190
KEGG Compound IDC01019
BioCyc IDL-FUCOSE
BiGG IDNot Available
Wikipedia LinkL-Fucose
METLIN IDNot Available
PubChem Compound17106
PDB IDNot Available
ChEBI ID2181
Good Scents IDrw1687501
References
General References
  1. Nicholson 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. [PubMed:7762816 ]
  2. Nakagawa 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. [PubMed:3757018 ]
  3. Condaminet 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. [PubMed:9842897 ]
  4. Havenaar 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. [PubMed:9613826 ]
  5. Roelfzema 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. [PubMed:6184420 ]
  6. Wiese 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. [PubMed:9133643 ]
  7. Isnard 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. [PubMed:15082343 ]
  8. Rizzi 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. [PubMed:9817848 ]
  9. Gheri 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. [PubMed:15481156 ]
  10. Fediv 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. [PubMed:11692712 ]
  11. Hutchinson 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. [PubMed:1849114 ]
  12. Fleischer M, Przondo-Mordarska A: [Adhesins of Acinetobacter strains]. Med Dosw Mikrobiol. 1998;50(3-4):229-37. [PubMed:10222738 ]
  13. Gohlke 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. [PubMed:8631761 ]
  14. Chien 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. [PubMed:15465338 ]
  15. Hanisch 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. [PubMed:8364932 ]
  16. Tonetti 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. [PubMed:9893952 ]
  17. Sato 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 beta1,3-glucosyltransferase, which is localized at the endoplasmic reticulum and glucosylates O-linked fucosylglycan on thrombospondin type 1 repeat domain. Glycobiology. 2006 Dec;16(12):1194-206. Epub 2006 Aug 9. [PubMed:16899492 ]
  18. Coyne 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. [PubMed:15774760 ]
  19. Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63. [PubMed:16086588 ]
  20. Bathi 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. [PubMed:11665403 ]
  21. Sakai 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. [PubMed:2311216 ]
  22. Yamauchi 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. [PubMed:8488966 ]