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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:24 UTC
HMDB IDHMDB01095
Secondary Accession NumbersNone
Metabolite Identification
Common NameGDP-L-fucose
DescriptionGDP-L-fucose is a sugar nucleotide and a readily available source of fucose. Fucose is a deoxyhexose that is found in nearly all plant and animal species. The monosaccharide plays several important metabolic roles in complex carbohydrates and in glycoproteins. Fucosylated oligosaccharides are involved in cell-cell recognition, selectin-mediated leukocyte-endothelial adhesion, and mouse embryogenesis. They form the basis of the Lewis-type blood group antigens, are involved in the formation of atherosclerosis, and mediate host-bacterial interactions. A decrease in the availability of fucose is associated with leukocyte adhesion deficiency type-II disorder, and fucosylated glycoproteins have been implicated in memory processes. Fucose is made available during the synthesis of fucosylated glycolipids, oligosaccharides, and glycoproteins via a sugar nucleotide intermediate, specifically GDP-L-fucose. GTP-L-fucose pyrophosphorylase (GFPP, E. C. 2.7.7.30) catalyzes the reversible condensation of guanosine triphosphate and beta-L-fucose-1-phosphate to form the nucleotide-sugar GDP-L-fucose. The enzyme functions primarily in the mammalian liver and kidney to salvage free L-fucose during the breakdown of glycolipids and glycoproteins. (PMID: 16086588 ).
Structure
Thumb
Synonyms
  1. (6-deoxy-beta-L-galactopyranosyl) ester
  2. GDP Fucose
  3. GDP-beta-L-Fucose
  4. Guanosine diphosphate fucose
  5. Guanosine diphosphofucose
Chemical FormulaC16H25N5O15P2
Average Molecular Weight589.3417
Monoisotopic Molecular Weight589.082238179
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl}oxy)phosphinic acid
CAS Registry Number15839-70-0
SMILES
C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1
InChI KeyLQEBEXMHBLQMDB-QIXZNPMTSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Nucleotide Sugars
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Purine Ribonucleoside Diphosphates
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Mixed Pentose/Hexose Disaccharide
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxane
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Nucleotide Sugars
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
ApplicationNot Available
Cellular locations
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility7.04 g/LALOGPS
logP-1.7ALOGPS
logP-4.5ChemAxon
logS-1.9ALOGPS
pKa (strongest acidic)1.93ChemAxon
pKa (strongest basic)1.31ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count15ChemAxon
hydrogen donor count9ChemAxon
polar surface area307.2ChemAxon
rotatable bond count8ChemAxon
refractivity116.97ChemAxon
polarizability47.87ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Golgi apparatus
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Skin
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021816
KNApSAcK IDNot Available
Chemspider ID388350
KEGG Compound IDC00325
BioCyc IDGUANOSINE_DIPHOSPHATE_FUCOSE
BiGG ID34623
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01095
Metagene LinkHMDB01095
METLIN ID6001
PubChem Compound439211
PDB IDNot Available
ChEBI ID17009
References
Synthesis ReferenceYamamoto, Kenji; Maruyama, Takashi; Kumagai, Hidehiko; Tochikura, Tatsurokuro; Seno, Taiko; Yamaguchi, Hideo. Preparation of GDP-L-fucose by using microbial enzymes. Agricultural and Biological Chemistry (1984), 48(3), 823-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Qi H, Fournier A, Grenier J, Fillion C, Labrie Y, Labrie C: Isolation of the novel human guanine nucleotide exchange factor Src homology 3 domain-containing guanine nucleotide exchange factor (SGEF) and of C-terminal SGEF, an N-terminally truncated form of SGEF, the expression of which is regulated by androgen in prostate cancer cells. Endocrinology. 2003 May;144(5):1742-52. Pubmed: 12697679
  2. Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63. Pubmed: 16086588
  3. Sawamura D, Abe R, Goto M, Akiyama M, Hemmi H, Akira S, Shimizu H: Direct injection of plasmid DNA into the skin induces dermatitis by activation of monocytes through toll-like receptor 9. J Gene Med. 2005 May;7(5):664-71. Pubmed: 15655803
  4. Sales ME, Sterin-Borda L, de Bracco MM, Rodriguez M, Narbaitz M, Borda E: IgA from HIV+ haemophilic patients triggers intracellular signals coupled to the cholinergic system of the intestine. Clin Exp Immunol. 1997 Nov;110(2):189-95. Pubmed: 9367401
  5. Palma AS, Morais VA, Coelho AV, Costa J: Effect of the manganese ion on human alpha3/4 fucosyltransferase III activity. Biometals. 2004 Feb;17(1):35-43. Pubmed: 14977360
  6. Yegorov YE, Kazimirchuk EV, Terekhov SM, Karachentsev DN, Shirokova EA, Khandazhinskaya AL, Meshcheryakova JA, Corey DR, Zelenin AV: Telomerase-dependent reactivation of DNA synthesis in macrophages implies alteration of telomeres. Cell Biol Int. 2002;26(12):1019-27. Pubmed: 12468377
  7. Coates SW Jr, Hogenauer C, Santa Ana CA, Rosenblatt RL, Emmett M, Fordtran JS: Inhibition of neutral sodium absorption by a prostaglandin analogue in patients with cystic fibrosis. Gastroenterology. 2004 Jul;127(1):65-72. Pubmed: 15236173
  8. Galiegue S, Mary S, Marchand J, Dussossoy D, Carriere D, Carayon P, Bouaboula M, Shire D, Le Fur G, Casellas P: Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem. 1995 Aug 15;232(1):54-61. Pubmed: 7556170
  9. Anfossi G, Russo I, Massucco P, Mattiello L, Doronzo G, De Salve A, Trovati M: Impaired synthesis and action of antiaggregating cyclic nucleotides in platelets from obese subjects: possible role in platelet hyperactivation in obesity. Eur J Clin Invest. 2004 Jul;34(7):482-9. Pubmed: 15255785
  10. Rastaldi MP, Armelloni S, Berra S, Li M, Pesaresi M, Poczewski H, Langer B, Kerjaschki D, Henger A, Blattner SM, Kretzler M, Wanke R, D'Amico G: Glomerular podocytes possess the synaptic vesicle molecule Rab3A and its specific effector rabphilin-3a. Am J Pathol. 2003 Sep;163(3):889-99. Pubmed: 12937130
  11. Sibley CP, Hochberg A, Boime I: Bromo-adenosine stimulates choriogonadotropin production in JAr and cytotrophoblast cells: evidence for effects on two stages of differentiation. Mol Endocrinol. 1991 Apr;5(4):582-6. Pubmed: 1922090
  12. Rosenfeldt HM, Hobson JP, Milstien S, Spiegel S: The sphingosine-1-phosphate receptor EDG-1 is essential for platelet-derived growth factor-induced cell motility. Biochem Soc Trans. 2001 Nov;29(Pt 6):836-9. Pubmed: 11709084
  13. Huopaniemi L, Kolmer M, Niittymaki J, Pelto-Huikko M, Renkonen R: Inflammation-induced transcriptional regulation of Golgi transporters required for the synthesis of sulfo sLex glycan epitopes. Glycobiology. 2004 Dec;14(12):1285-94. Epub 2004 Jul 21. Pubmed: 15269183
  14. Noda K, Miyoshi E, Gu J, Gao CX, Nakahara S, Kitada T, Honke K, Suzuki K, Yoshihara H, Yoshikawa K, Kawano K, Tonetti M, Kasahara A, Hori M, Hayashi N, Taniguchi N: Relationship between elevated FX expression and increased production of GDP-L-fucose, a common donor substrate for fucosylation in human hepatocellular carcinoma and hepatoma cell lines. Cancer Res. 2003 Oct 1;63(19):6282-9. Pubmed: 14559815
  15. Jakob G, Mair J, Vorderwinkler KP, Judmaier G, Konig P, Zwierzina H, Pichler M, Puschendorf B: Clinical significance of urinary cyclic guanosine monophosphate in diagnosis of heart failure. Clin Chem. 1994 Jan;40(1):96-100. Pubmed: 8287551
  16. da Silva CD, Brunini TM, Reis PF, Moss MB, Santos SF, Roberts NB, Ellory JC, Mann GE, Mendes-Ribeiro AC: Effects of nutritional status on the L-arginine-nitric oxide pathway in platelets from hemodialysis patients. Kidney Int. 2005 Nov;68(5):2173-9. Pubmed: 16221216
  17. Andre M, Latado H, Felley-Bosco E: Inducible nitric oxide synthase-dependent stimulation of PKGI and phosphorylation of VASP in human embryonic kidney cells. Biochem Pharmacol. 2005 Feb 15;69(4):595-602. Epub 2004 Dec 22. Pubmed: 15670578
  18. Benitah SA, Frye M, Glogauer M, Watt FM: Stem cell depletion through epidermal deletion of Rac1. Science. 2005 Aug 5;309(5736):933-5. Pubmed: 16081735

Enzymes

General function:
Involved in fucose-1-phosphate guanylyltransferase acti
Specific function:
Catalyzes the formation of GDP-L-fucose from GTP and L-fucose-1-phosphate. Functions as a salvage pathway to reutilize L-fucose arising from the turnover of glycoproteins and glycolipids.
Gene Name:
FPGT
Uniprot ID:
O14772
Molecular weight:
37630.405
Reactions
Guanosine triphosphate + Fucose 1-phosphate → Pyrophosphate + GDP-L-fucosedetails
General function:
Involved in galactoside 2-alpha-L-fucosyltransferase activity
Specific function:
Creates a soluble precursor oligosaccharide FuC-alpha ((1,2)Galbeta-) called the H antigen which is an essential substrate for the final step in the soluble A and B antigen synthesis pathway. H and Se enzymes fucosylate the same acceptor substrates but exhibit different Km values.
Gene Name:
FUT2
Uniprot ID:
Q10981
Molecular weight:
39016.84
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Guanosine diphosphate + alpha-L-fucosyl-(1->2)-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
General function:
Involved in galactoside 2-alpha-L-fucosyltransferase activity
Specific function:
Creates a soluble precursor oligosaccharide FuC-alpha ((1,2)Galbeta-) called the H antigen which is an essential substrate for the final step in the soluble A and B antigen synthesis pathway. H and Se enzymes fucosylate the same acceptor substrates but exhibit different Km values.
Gene Name:
FUT1
Uniprot ID:
P19526
Molecular weight:
41251.11
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Guanosine diphosphate + alpha-L-fucosyl-(1->2)-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
General function:
Involved in catalytic activity
Specific function:
Two step NADP-dependent conversion of GDP-4-dehydro-6-deoxy-D-mannose to GDP-fucose, involving an epimerase and a reductase reaction.
Gene Name:
TSTA3
Uniprot ID:
Q13630
Molecular weight:
35892.46
Reactions
GDP-L-fucose + NADP → GDP-4-Dehydro-6-deoxy-D-mannose + NADPHdetails
GDP-L-fucose + NADP → GDP-4-Dehydro-6-deoxy-D-mannose + NADPH + Hydrogen Iondetails
General function:
Involved in fucosyltransferase activity
Specific function:
May catalyze alpha-1,3 glycosidic linkages involved in the expression of VIM-2, Lewis X/SSEA-1 and sialyl Lewis X antigens.
Gene Name:
FUT5
Uniprot ID:
Q11128
Molecular weight:
42988.655
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R → Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-Rdetails
General function:
Involved in fucosyltransferase activity
Specific function:
Transfers a fucose to lacto-N-neotetraose but not to either alpha2,3-sialyl lacto-N-neotetraose or lacto-N-tetraose. Can catalyze the last step in the biosynthesis of Lewis antigen, the addition of a fucose to precursor polysaccharides
Gene Name:
FUT9
Uniprot ID:
Q9Y231
Molecular weight:
42040.7
General function:
Involved in glycoprotein 6-alpha-L-fucosyltransferase activity
Specific function:
Catalyzes the addition of fucose in alpha 1-6 linkage to the first GlcNAc residue, next to the peptide chains in N-glycans.
Gene Name:
FUT8
Uniprot ID:
Q9BYC5
Molecular weight:
66515.32
Reactions
GDP-L-fucose + N(4)-(N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->3)-(N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->6))-beta-D-mannosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-beta-D-glucosaminyl)asparagine → Guanosine diphosphate + N(4)-(N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->3)-(N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->6))-beta-D-mannosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->4)-(alpha-L-fucosyl-(1->6))-N-acetyl-beta-D-glucosaminyl)asparaginedetails
General function:
Involved in fucosyltransferase activity
Specific function:
Enzyme involved in the biosynthesis of the E-Selectin ligand, sialyl-Lewis X. Catalyzes the transfer of fucose from GDP-beta-fucose to alpha-2,3 sialylated substrates.
Gene Name:
FUT6
Uniprot ID:
P51993
Molecular weight:
41859.42
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R → Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-Rdetails
General function:
Involved in fucosyltransferase activity
Specific function:
May catalyze alpha-1,3 glycosidic linkages involved in the expression of sialyl Lewis X antigens.
Gene Name:
FUT7
Uniprot ID:
Q11130
Molecular weight:
39238.495
Reactions
GDP-L-fucose + alpha-2,3-Neu-N-acetyl-1,4-beta-D-galactosyl-N-acetyl-D-glucosaminyl-R → Guanosine diphosphate + alpha-2,3-Neu-N-acetyl-1,4-beta-D-galactosyl-(alpha-1,3-L-fucosyl)-N-acetyl-D-glucosaminyl-Rdetails
General function:
Not Available
Specific function:
May catalyze alpha-1,3 and alpha-1,4 glycosidic linkages involved in the expression of Vim-2, Lewis A, Lewis B, sialyl Lewis X and Lewis X/SSEA-1 antigens. May be involved in blood group Lewis determination; Lewis-positive (Le(+)) individuals have an active enzyme while Lewis-negative (Le(-)) individuals have an inactive enzyme. Also acts on the corresponding 1,4-galactosyl derivative, forming 1,3-L-fucosyl links.
Gene Name:
FUT3
Uniprot ID:
P21217
Molecular weight:
42116.69
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R → Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-Rdetails