2.0 2015-09-08 17:50:22 -0600 2015-09-14 16:46:02 -0600 ECMDB24243 M2MDB006360 GDP-β-L-fucose GDP-beta-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-beta-L-fucose.GDP-beta-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-beta-L-fucose. C16H23N5O15P2 587.329 587.067686216 [5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(3,4,5-trihydroxy-6-methyloxan-2-yl phosphonato)oxy]phosphonate [5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (3,4,5-trihydroxy-6-methyloxan-2-yl phosphonato)oxyphosphonate CC1OC(OP([O-])(=O)OP([O-])(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(N)=NC3=O)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)/p-2 LQEBEXMHBLQMDB-UHFFFAOYSA-L logp -1.15 ALOGPS logs -1.87 ALOGPS solubility 8.49e+00 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac [5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(3,4,5-trihydroxy-6-methyloxan-2-yl phosphonato)oxy]phosphonate ChemAxon average_mass 587.329 ChemAxon mono_mass 587.067686216 ChemAxon smiles CC1OC(OP([O-])(=O)OP([O-])(=O)OCC2OC(C(O)C2O)N2C=NC3=C2NC(N)=NC3=O)C(O)C(O)C1O ChemAxon formula C16H23N5O15P2 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)/p-2 ChemAxon inchikey LQEBEXMHBLQMDB-UHFFFAOYSA-L ChemAxon polar_surface_area 312.86 ChemAxon refractivity 114.29 ChemAxon polarizability 50 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 16 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge -2 ChemAxon Amino sugar and nucleotide sugar metabolism II The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. The beta-D-fructofuranose 6 -phosphate is isomerized in a reversible reaction into an alpha-D-mannose 6-phosphate. This compound can also be introduced into the cell from the periplasmic space through a mannose PTS permease that phosphorylates an alpha-D-mannose. Alpha-D-mannose 6-phosphate undergoes a reversible reaction through a phosphomannomutase to produce an alpha-D-mannose 1-phosphate. The alpha-D-mannose 1-phosphate enters the nucleotide sugar metabolism through a reaction with GTP producing a GDP-mannose and releasing a pyrophosphate, all through a mannose-1-phosphate guanylyltransferase. GDP-mannose is then dehydrated to produce GDP-4-dehydro-6-deoxy-alpha-D-mannose through a GDP-mannose 4,6-dehydratase. This compound is then used to synthesize GDP-Beta-L-fucose through a NADPH dependent GDP-L-fucose synthase. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000887 Metabolic Specdb::NmrOneD 276878 Specdb::NmrOneD 276879 Specdb::NmrOneD 276880 Specdb::NmrOneD 276881 Specdb::NmrOneD 276882 Specdb::NmrOneD 276883 Specdb::NmrOneD 276884 Specdb::NmrOneD 276885 Specdb::NmrOneD 276886 Specdb::NmrOneD 276887 Specdb::NmrOneD 276888 Specdb::NmrOneD 276889 Specdb::NmrOneD 276890 Specdb::NmrOneD 276891 Specdb::NmrOneD 276892 Specdb::NmrOneD 276893 Specdb::NmrOneD 276894 Specdb::NmrOneD 276895 Specdb::NmrOneD 276896 Specdb::NmrOneD 276897 Specdb::MsMs 25562 Specdb::MsMs 25563 Specdb::MsMs 25564 Specdb::MsMs 32120 Specdb::MsMs 32121 Specdb::MsMs 32122 GDP-L-fucose synthase P32055 FCL_ECOLI fcl http://ecmdb.ca/proteins/P32055.xml GDP-4-dehydro-6-deoxy-α-D-mannose + NADPH + Hydrogen ion + NADPH > NADP + GDP-β-L-fucose PW_R003363