1.02011-04-11 17:01:44 UTC2019-11-26 03:20:54 UTCFDB021816GDP-L-fucoseGDP-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](6-Deoxy-beta-L-galactopyranosyl) esterGDP FucoseGDP-beta-L-FucoseGuanosine diate fucoseGuanosine diofucoseC16H25N5O15P2589.3417589.082238179[({[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{[3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)phosphinic acid15839-70-0CC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1OInChI=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)LQEBEXMHBLQMDB-UHFFFAOYSA-N 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.Purine nucleotide sugarsOrganic compoundsNucleosides, nucleotides, and analoguesPurine nucleotidesPurine nucleotide sugarsAromatic heteropolycyclic compounds6-oxopurinesAminopyrimidines and derivativesAzacyclic compoundsGlycosylaminesHeteroaromatic compoundsHydrocarbon derivativesHypoxanthinesMonoalkyl phosphatesMonosaccharide phosphatesN-substituted imidazolesOrganic oxidesOrganic pyrophosphatesOrganopnictogen compoundsOxacyclic compoundsOxanesPentose phosphatesPolyolsPrimary aminesPurine ribonucleoside diphosphatesPurine ribonucleoside monophosphatesPyrimidonesSecondary alcoholsTetrahydrofuransVinylogous amides6-oxopurineAlcoholAlkyl phosphateAmineAminopyrimidineAromatic heteropolycyclic compoundAzacycleAzoleGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeHypoxanthineImidazoleImidazopyrimidineMonoalkyl phosphateMonosaccharideMonosaccharide phosphateN-glycosyl compoundN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic pyrophosphateOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacycleOxanePentose phosphatePentose-5-phosphatePhosphoric acid esterPolyolPrimary aminePurinePurine nucleotide sugarPurine ribonucleoside diphosphatePurine ribonucleoside monophosphatePyrimidinePyrimidoneSecondary alcoholTetrahydrofuranVinylogous amideSolidlogp-1.45logs-1.92solubility7.02e+00 g/llogp-4.7pka_strongest_acidic1.71pka_strongest_basic3.38iupac[({[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 acidaverage_mass589.3417mono_mass589.082238179smilesCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1OformulaC16H25N5O15P2inchiInChI=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)inchikeyLQEBEXMHBLQMDB-UHFFFAOYSA-Npolar_surface_area308.19refractivity127.55polarizability50.36rotatable_bond_count8acceptor_count16donor_count10physiological_charge-2formal_charge0Fructose and Mannose DegradationSMP00064map00051Specdb::CMs892731Specdb::CMs892732Specdb::CMs892733Specdb::CMs892734Specdb::CMs892735Specdb::CMs892736Specdb::CMs892737Specdb::CMs892738Specdb::CMs892739Specdb::CMs892740Specdb::CMs892741Specdb::CMs892742Specdb::CMs892743Specdb::CMs892744Specdb::CMs892745Specdb::CMs892746Specdb::CMs892747Specdb::CMs892748Specdb::CMs892749Specdb::CMs892750Specdb::CMs892751Specdb::CMs892752Specdb::CMs892753Specdb::CMs892754Specdb::CMs892755Specdb::MsMs3436010Specdb::MsMs3436011Specdb::MsMs3436012Specdb::MsMs3436879Specdb::MsMs3436880Specdb::MsMs3436881Specdb::NmrOneD187601Specdb::NmrOneD187602Specdb::NmrOneD187603Specdb::NmrOneD187604Specdb::NmrOneD187605Specdb::NmrOneD187606Specdb::NmrOneD187607Specdb::NmrOneD187608Specdb::NmrOneD187609Specdb::NmrOneD187610Specdb::NmrOneD187611Specdb::NmrOneD187612Specdb::NmrOneD187613Specdb::NmrOneD187614Specdb::NmrOneD187615Specdb::NmrOneD187616Specdb::NmrOneD187617Specdb::NmrOneD187618Specdb::NmrOneD187619Specdb::NmrOneD187620HMDB01095#<Reference:0x00005556762ddda0>#<Reference:0x00005556762ddad0>#<Reference:0x00005556762dd648>#<Reference:0x00005556762dd3a0>#<Reference:0x00005556762dd0f8>#<Reference:0x00005556762dcea0>#<Reference:0x00005556762dccc0>#<Reference:0x00005556762dc9a0>#<Reference:0x00005556762dc798>#<Reference:0x00005556762dc450>#<Reference:0x00005556762dc158>#<Reference:0x00005556762dbde8>#<Reference:0x00005556762db8e8>#<Reference:0x00005556762db618>#<Reference:0x00005556762db370>#<Reference:0x00005556762db190>#<Reference:0x00005556762daf88>#<Reference:0x00005556762dacb8>Milk (Cow)Type 2specific33.733.733.7uMAlpha-(1,3)-fucosyltransferaseQ9Y231FUT9Alpha-(1,6)-fucosyltransferaseQ9BYC5FUT8Galactoside 2-alpha-L-fucosyltransferase 1P19526FUT1Galactoside 2-alpha-L-fucosyltransferase 2Q10981FUT2GDP-L-fucose synthaseQ13630TSTA3