1.0 2011-04-11 17:01:44 UTC 2019-11-26 03:20:54 UTC FDB021816 GDP-L-fucose 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] (6-Deoxy-beta-L-galactopyranosyl) ester GDP Fucose GDP-beta-L-Fucose Guanosine diate fucose Guanosine diofucose C16H25N5O15P2 589.3417 589.082238179 [({[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 acid 15839-70-0 CC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O 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) 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 sugars Organic compounds Nucleosides, nucleotides, and analogues Purine nucleotides Purine nucleotide sugars Aromatic heteropolycyclic compounds 6-oxopurines Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hypoxanthines Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Oxanes Pentose phosphates Polyols Primary amines Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Pyrimidones Secondary alcohols Tetrahydrofurans Vinylogous amides 6-oxopurine Alcohol Alkyl phosphate Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hypoxanthine Imidazole Imidazopyrimidine Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Polyol Primary amine Purine Purine nucleotide sugar Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Pyrimidine Pyrimidone Secondary alcohol Tetrahydrofuran Vinylogous amide Solid logp -1.45 ALOGPS logs -1.92 ALOGPS solubility 7.02e+00 g/l ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 1.71 ChemAxon pka_strongest_basic 3.38 ChemAxon iupac [({[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 ChemAxon average_mass 589.3417 ChemAxon mono_mass 589.082238179 ChemAxon smiles CC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(=N)N=C3O)C(O)C(O)C1O ChemAxon formula C16H25N5O15P2 ChemAxon inchi 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) ChemAxon inchikey LQEBEXMHBLQMDB-UHFFFAOYSA-N ChemAxon polar_surface_area 308.19 ChemAxon refractivity 127.55 ChemAxon polarizability 50.36 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 16 ChemAxon donor_count 10 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Fructose and Mannose Degradation SMP00064 map00051 Specdb::NmrOneD 187601 Specdb::NmrOneD 187602 Specdb::NmrOneD 187603 Specdb::NmrOneD 187604 Specdb::NmrOneD 187605 Specdb::NmrOneD 187606 Specdb::NmrOneD 187607 Specdb::NmrOneD 187608 Specdb::NmrOneD 187609 Specdb::NmrOneD 187610 Specdb::NmrOneD 187611 Specdb::NmrOneD 187612 Specdb::NmrOneD 187613 Specdb::NmrOneD 187614 Specdb::NmrOneD 187615 Specdb::NmrOneD 187616 Specdb::NmrOneD 187617 Specdb::NmrOneD 187618 Specdb::NmrOneD 187619 Specdb::NmrOneD 187620 Specdb::CMs 892731 Specdb::CMs 892732 Specdb::CMs 892733 Specdb::CMs 892734 Specdb::CMs 892735 Specdb::CMs 892736 Specdb::CMs 892737 Specdb::CMs 892738 Specdb::CMs 892739 Specdb::CMs 892740 Specdb::CMs 892741 Specdb::CMs 892742 Specdb::CMs 892743 Specdb::CMs 892744 Specdb::CMs 892745 Specdb::CMs 892746 Specdb::CMs 892747 Specdb::CMs 892748 Specdb::CMs 892749 Specdb::CMs 892750 Specdb::CMs 892751 Specdb::CMs 892752 Specdb::CMs 892753 Specdb::CMs 892754 Specdb::CMs 892755 Specdb::MsMs 3436010 Specdb::MsMs 3436011 Specdb::MsMs 3436012 Specdb::MsMs 3436879 Specdb::MsMs 3436880 Specdb::MsMs 3436881 HMDB01095 #<Reference:0x000055ce31f235c8> #<Reference:0x000055ce31f23410> #<Reference:0x000055ce31f23258> #<Reference:0x000055ce31f230a0> #<Reference:0x000055ce31f22ee8> #<Reference:0x000055ce31f22d30> #<Reference:0x000055ce31f22b78> #<Reference:0x000055ce31f229c0> #<Reference:0x000055ce31f22808> #<Reference:0x000055ce31f22650> #<Reference:0x000055ce31f22498> #<Reference:0x000055ce31f222e0> #<Reference:0x000055ce31f22100> #<Reference:0x000055ce31f21f48> #<Reference:0x000055ce31f21d90> #<Reference:0x000055ce31f21bd8> #<Reference:0x000055ce31f21a20> #<Reference:0x000055ce31f21868> Milk (Cow) Type 2 specific 33.7 33.7 33.7 uM Alpha-(1,3)-fucosyltransferase Q9Y231 FUT9 Alpha-(1,6)-fucosyltransferase Q9BYC5 FUT8 Galactoside 2-alpha-L-fucosyltransferase 1 P19526 FUT1 Galactoside 2-alpha-L-fucosyltransferase 2 Q10981 FUT2 GDP-L-fucose synthase Q13630 TSTA3