Human Metabolome Database Version 3.5

Showing metabocard for GDP-L-fucose (HMDB01095)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:24 -0600
HMDB ID HMDB01095
Secondary Accession Numbers None
Metabolite Identification
Common Name GDP-L-fucose
Description GDP-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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (6-deoxy-beta-L-galactopyranosyl) ester
  2. GDP Fucose
  3. GDP-beta-L-Fucose
  4. Guanosine diphosphate fucose
  5. Guanosine diphosphofucose
Chemical Formula C16H25N5O15P2
Average Molecular Weight 589.3417
Monoisotopic Molecular Weight 589.082238179
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 Number 15839-70-0
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 Key LQEBEXMHBLQMDB-QIXZNPMTSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine 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 Parent Purine Nucleotide Sugars
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
Application Not Available
Cellular locations
  • Golgi apparatus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 7.04 g/L ALOGPS
LogP -1.69 ALOGPS
LogP -4.5 ChemAxon
LogS -1.92 ALOGPS
pKa (strongest acidic) 1.93 ChemAxon
pKa (strongest basic) 1.31 ChemAxon
Hydrogen Acceptor Count 15 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 307.2 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 116.97 ChemAxon
Polarizability 47.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Golgi apparatus
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Kidney
  • Prostate
  • Skin
  • Platelet
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021816
KNApSAcK ID Not Available
Chemspider ID 388350 Link_out
KEGG Compound ID C00325 Link_out
BioCyc ID GUANOSINE_DIPHOSPHATE_FUCOSE Link_out
BiGG ID 34623 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01095 Link_out
Metagene Link HMDB01095 Link_out
METLIN ID 6001 Link_out
PubChem Compound 439211 Link_out
PDB ID Not Available
ChEBI ID 17009 Link_out
References
Synthesis Reference Yamamoto, 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. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. 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 Link_out
  16. 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 Link_out
  17. 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 Link_out
  18. Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63. Pubmed: 16086588 Link_out

Enzymes
Name: Fucose-1-phosphate guanylyltransferase
Reactions:
Guanosine triphosphate + Fucose 1-phosphate unknown Pyrophosphate + GDP-L-fucose details
Gene Name: FPGT
Uniprot ID: O14772 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactoside 2-alpha-L-fucosyltransferase 2
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 unknown 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)-ceramide details
Gene Name: FUT2
Uniprot ID: Q10981 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactoside 2-alpha-L-fucosyltransferase 1
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 unknown 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)-ceramide details
Gene Name: FUT1
Uniprot ID: P19526 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GDP-L-fucose synthase
Reactions:
GDP-L-fucose + NADP unknown GDP-4-Dehydro-6-deoxy-D-mannose + NADPH details
GDP-L-fucose + NADP unknown GDP-4-Dehydro-6-deoxy-D-mannose + NADPH + Hydrogen Ion details
Gene Name: TSTA3
Uniprot ID: Q13630 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-(1,3)-fucosyltransferase
Reactions:
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R unknown Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-R details
Gene Name: FUT5
Uniprot ID: Q11128 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-(1,3)-fucosyltransferase
Reactions: Not Available
Gene Name: FUT9
Uniprot ID: Q9Y231 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-(1,6)-fucosyltransferase
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 unknown 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)asparagine details
Gene Name: FUT8
Uniprot ID: Q9BYC5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-(1,3)-fucosyltransferase
Reactions:
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R unknown Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-R details
Gene Name: FUT6
Uniprot ID: P51993 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-(1,3)-fucosyltransferase
Reactions:
GDP-L-fucose + alpha-2,3-Neu-N-acetyl-1,4-beta-D-galactosyl-N-acetyl-D-glucosaminyl-R unknown Guanosine diphosphate + alpha-2,3-Neu-N-acetyl-1,4-beta-D-galactosyl-(alpha-1,3-L-fucosyl)-N-acetyl-D-glucosaminyl-R details
Gene Name: FUT7
Uniprot ID: Q11130 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactoside 3(4)-L-fucosyltransferase
Reactions:
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R unknown Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-R details
Gene Name: FUT3
Uniprot ID: P21217 Link_out
Protein Sequence: FASTA