Record Information |
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Version | 1.0 |
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Creation date | 2011-04-11 17:01:44 UTC |
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Update date | 2019-11-26 03:20:54 UTC |
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Primary ID | FDB021816 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | GDP-L-fucose |
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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) [HMDB] |
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CAS Number | 15839-70-0 |
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Structure | |
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Synonyms | Synonym | Source |
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Diphosphate fucose, guanosine | MeSH | Fucose, guanosine diphosphate | MeSH | Fucose, GDP | MeSH | Guanosine diphosphate fucose | MeSH | Guanosine diphosphofucose | MeSH | Diphosphofucose, guanosine | MeSH | GDP Fucose | MeSH | (6-Deoxy-beta-L-galactopyranosyl) ester | HMDB | GDP-beta-L-Fucose | HMDB | Guanosine diate fucose | HMDB | Guanosine diofucose | HMDB |
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Predicted Properties | |
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Chemical Formula | C16H25N5O15P2 |
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IUPAC name | [({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phosphinic acid |
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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) |
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InChI Key | LQEBEXMHBLQMDB-UHFFFAOYSA-N |
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Isomeric SMILES | CC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O |
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Average Molecular Weight | 589.3417 |
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Monoisotopic Molecular Weight | 589.082238179 |
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Classification |
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Description | belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine nucleotide sugars |
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Direct Parent | Purine nucleotide sugars |
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Alternative Parents | |
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Substituents | - Purine nucleotide sugar
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Monosaccharide phosphate
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Pyrimidone
- Pyrimidine
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Alkyl phosphate
- Tetrahydrofuran
- Vinylogous amide
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Polyol
- Oxacycle
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organopnictogen compound
- Alcohol
- Primary amine
- Organonitrogen compound
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Not Available |
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External Links |
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ChemSpider ID | 388350 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00325 |
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Pubchem Compound ID | 439211 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB01095 |
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CRC / DFC (Dictionary of Food Compounds) ID | FOG76-Z:FOG76-Z |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 34623 |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Alpha-(1,3)-fucosyltransferase | FUT9 | Q9Y231 | Galactoside 2-alpha-L-fucosyltransferase 2 | FUT2 | Q10981 | Galactoside 2-alpha-L-fucosyltransferase 1 | FUT1 | P19526 | GDP-L-fucose synthase | TSTA3 | Q13630 | Alpha-(1,6)-fucosyltransferase | FUT8 | Q9BYC5 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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