2.0 2012-05-31 13:45:07 -0600 2015-06-03 15:53:43 -0600 ECMDB01095 M2MDB000252 GDP-L-Fucose GDP-L-fucose is a sugar nucleotide and a readily available source of fucose. 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. 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. (6-Deoxy-b-L-galactopyranosyl) ester (6-deoxy-beta-L-galactopyranosyl) ester (6-Deoxy-β-L-galactopyranosyl) ester 2-amino-9-[3,4-dihydroxy-5-[[hydroxy-[hydroxy-(3,4,5-trihydroxy- 6-methyl-tetrahydropyran-2-yl)oxy-phosphinoyl]oxy-phosphinoyl] oxymethyl]tetrahydrofuran-2-yl]-1,9-dihydropurin-6-one GDP Fucose GDP-b-L-Fucose GDP-beta-L-Fucose GDP-fucose GDP-β-L-Fucose Guanosine 5'-(trihydrogen diphosphate), P'-(6-deoxy-&beta;-L- galactopyranosyl) ester Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-&beta;-L- galactopyranosyl) ester Guanosine diphosphate fucose Guanosine diphosphofucose Guanosine diphosphoric acid fucose C16H25N5O15P2 589.3417 589.082238179 [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid gdp-L-fucose 15839-70-0 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=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 LQEBEXMHBLQMDB-QIXZNPMTSA-N Solid Cytosol logp -1.69 ALOGPS logs -1.92 ALOGPS solubility 7.04e+00 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 589.3417 ChemAxon mono_mass 589.082238179 ChemAxon 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 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)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1 ChemAxon inchikey LQEBEXMHBLQMDB-QIXZNPMTSA-N ChemAxon polar_surface_area 307.2 ChemAxon refractivity 116.97 ChemAxon polarizability 48.22 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Amino sugar and nucleotide sugar metabolism ec00520 Metabolic pathways eco01100 Mannose Metabolism D-mannose can serve as a total source of carbon and energy for growth of E. coli. Alpha-D-mannose is introduced into the cytoplasm through a mannose PTS permease. Because mannose is taken up via a phosphotransferase system (PTS), the first intracellular species is D-mannose-6-phosphate. mannose-6-phosphate isomerase converts D-mannose-6-phosphate to D-fructose-6-phosphate, an intermediate of glycolysis, and hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. The first two enzymes in the pathway (SEE VERTICAL SECTION) catalyze isomerizations that interconvert phosphorylated aldohexoses (β-D-glucose-6-phosphate, D-mannose-6-phosphate) and phosphorylated ketohexoses (D-fructose-6-phosphate). The reaction catalyzed by mannose-6-phosphate isomerase that produces D-mannose-6-phosphate is the first committed step in the biosynthesis of the activated mannose donor GDP-α-D-mannose. D-mannose-6-phosphate is then converted to GDP-D-mannose by the interaction of phosphomannomutase and mannose-1-phosphate guanylyltransferase . As for the bottom part L-fucose is biosynthesized as the sugar nucleotide GDP-L-fucose. Its biosynthesis from GDP-D-mannose begins with dehydration of this compound to GDP-4-dehydro-6-deoxy-D-mannose by the product of gene gmd. Then the bifunctional GDP-fucose synthase catalyzes the two-step (epimerase/reductase) synthesis of GDP-fucose from GDP-4-dehydro-6-deoxy-D-mannose via a GDP-4-dehydro-6-L-deoxygalactose intermediate. L-fucose is then incorporated into the colanic acid building blocks biosynthesis pathway. PW000822 Metabolic colanic acid building blocks biosynthesis The colonic acid building blocks biosynthesis starts with a Beta-D-Glucose undergoing a transport reaction mediated by a glucose PTS permease. The permease phosphorylates the Beta-D-Glucose, producing a Beta-D-Glucose 6-phosphate. This compound can either change to an Alpha-D-Glucose 6-phosphate spontaneously or into a fructose 6-phosphate through a glucose-6-phosphate isomerase. The latter compound can also be present in E.coli through the interaction of D-fructose and a mannose PTS permease which phosphorylate the D-fructose. Fructose 6-phosphate interacts in a reversible reaction with mannose-6-phosphate isomerase in order to produce a Alpha-D-mannose 6-phosphate. This compound can also be present in E.coli through the interaction of Alpha-D-mannose and a mannose PTS permease which phosphorylates the alpha-D-mannose. Alpha-D-mannose 6-phosphate interacts in a reversible reaction with a phosphomannomutase to produce a alpha-D-mannose 1-phosphate. This compound in turn with a hydrogen ion and gtp undergoes a reaction with a mannose-1-phosphate guanylyltransferase, releasing a pyrophosphate and producing a guanosine diphosphate mannose. Guanosine diphosphate mannose interacts with gdp-mannose 4,6-dehydratase releasing a water, and gdp-4-dehydro-6-deoxy-D-mannose. This compound in turn with hydrogen ion and NADPH interact with GDP-L-fucose synthase releasing NADP and producing a GDP-L-fucose. The Alpha-D-Glucose 6-phosphate interacts in a reversible reaction with phosphoglucomutase-1 to produce a alpha-D-glucose 1-phosphate. This in turn with UTP and hydrogen ion interact with UTP--glucose-1-phosphate uridyleltransferase releasing a pyrophosphate and UDP-glucose. UDP-glucose can either interact with galactose-1-phosphate uridylyltransferase to produce a UDP-galactose or in turn with NAD and water interact with UDP-glucose 6-dehydrogenase releasing a NADH and a hydrogen ion and producing a UDP-glucuronate. GDP-L-fucose, UDP-glucose, UDP-galactose and UDP-glucuronate are sugars that need to be activated in the form of nucleotide sugar prior to their assembly into colanic acid, also known as M antigen. Colanic acid is an extracellular polysaccharide which has been linked to a cluster of 19 genes(wca). PW000951 Metabolic GDP-L-fucose biosynthesis I (from GDP-D-mannose) PWY-66 Specdb::CMs 20842 Specdb::CMs 37924 Specdb::CMs 282849 Specdb::CMs 414401 Specdb::CMs 414402 Specdb::CMs 414403 Specdb::CMs 414404 Specdb::CMs 414405 Specdb::CMs 414406 Specdb::CMs 414407 Specdb::CMs 414408 Specdb::CMs 414409 Specdb::CMs 414410 Specdb::CMs 414411 Specdb::CMs 414412 Specdb::CMs 414413 Specdb::CMs 414414 Specdb::CMs 414415 Specdb::CMs 414416 Specdb::CMs 414417 Specdb::CMs 414418 Specdb::CMs 414419 Specdb::CMs 414420 Specdb::CMs 414421 Specdb::CMs 414422 Specdb::NmrOneD 146390 Specdb::NmrOneD 146391 Specdb::NmrOneD 146392 Specdb::NmrOneD 146393 Specdb::NmrOneD 146394 Specdb::NmrOneD 146395 Specdb::NmrOneD 146396 Specdb::NmrOneD 146397 Specdb::NmrOneD 146398 Specdb::NmrOneD 146399 Specdb::NmrOneD 146400 Specdb::NmrOneD 146401 Specdb::NmrOneD 146402 Specdb::NmrOneD 146403 Specdb::NmrOneD 146404 Specdb::NmrOneD 146405 Specdb::NmrOneD 146406 Specdb::NmrOneD 146407 Specdb::NmrOneD 146408 Specdb::NmrOneD 146409 Specdb::MsMs 27491 Specdb::MsMs 27492 Specdb::MsMs 27493 Specdb::MsMs 34049 Specdb::MsMs 34050 Specdb::MsMs 34051 Specdb::MsMs 2308263 Specdb::MsMs 2308264 Specdb::MsMs 2308265 Specdb::MsMs 2653589 Specdb::MsMs 2653590 Specdb::MsMs 2653591 HMDB01095 27505 388350 C00325 17009 GUANOSINE_DIPHOSPHATE_FUCOSE Keseler, I. 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GDP-L-fucose synthase P32055 FCL_ECOLI fcl http://ecmdb.ca/proteins/P32055.xml GDP-4-Oxo-L-fucose + Hydrogen ion + NADPH > GDP-L-Fucose + NADP GDP-L-Fucose + NADP <> GDP-4-Dehydro-6-deoxy-D-mannose + NADPH + Hydrogen ion R05692 1.1.1.271-RXN GDP-L-Fucose + UDP-Glucose + Uridine diphosphate glucuronic acid + Uridine diphosphategalactose colanic acid RXN0-5377 GDP-L-Fucose + NADP < Hydrogen ion + NADPH + GDP-4-Dehydro-6-deoxy-D-mannose 1.1.1.271-RXN GDP-L-Fucose + NADP > GDP-4-Dehydro-6-deoxy-D-mannose + NADPH R05692 1.1.1.271-RXN GDP-4-Dehydro-6-deoxy-D-mannose + NADPH + Hydrogen ion + NADPH > GDP-L-Fucose + NADP PW_R002963