2.0 2015-09-08 17:50:22 -0600 2015-09-14 16:46:44 -0600 ECMDB24242 M2MDB006359 GDP-4-dehydro-6-deoxy-α-D-mannose GDP-4-dehydro-6-deoxy-alpha-D-mannose is an intermediate in GDP-L-fucose biosynthesis I (from GDP-D-mannose) in E.coli. It is a substrate for the enzyme GDP-fucose synthase which catalyzes the reaction GDP-4-dehydro-6-deoxy-alpha-D-mannose + NADPH + H+ -> GDP-beta-L-fucose + NADP+. It is also a product for enzyme GDP-mannose 4,6-dehydratase which catalyzes reaction GDP-alpha-D-mannose -> GDP-4-dehydro-6-deoxy-alpha-D-mannose + H2O (BioCYc compound: GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE). C16H21N5O15P2 585.313 585.052036152 9-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate 9-[(2R,3R,4S,5R)-5-[({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-imino-3H-purin-6-olate [H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)C(=O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O InChI=1S/C16H23N5O15P2/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/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1 PNHLMHWWFOPQLK-BKUUWRAGSA-L logp -1.36 ALOGPS logs -1.91 ALOGPS solubility 7.65e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 1.71 ChemAxon pka_strongest_basic 2.78 ChemAxon iupac 9-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate ChemAxon average_mass 585.313 ChemAxon mono_mass 585.052036152 ChemAxon smiles [H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)C(=O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3[O-])[C@]([H])(O)[C@]1([H])O ChemAxon formula C16H21N5O15P2 ChemAxon inchi InChI=1S/C16H23N5O15P2/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/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1 ChemAxon inchikey PNHLMHWWFOPQLK-BKUUWRAGSA-L ChemAxon polar_surface_area 310.69 ChemAxon refractivity 136.21 ChemAxon polarizability 48.47 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 16 ChemAxon donor_count 7 ChemAxon physiological_charge -2 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 281679 Specdb::NmrOneD 281680 Specdb::NmrOneD 281681 Specdb::NmrOneD 281682 Specdb::NmrOneD 281683 Specdb::NmrOneD 281684 Specdb::NmrOneD 281685 Specdb::NmrOneD 281686 Specdb::NmrOneD 281687 Specdb::NmrOneD 281688 Specdb::NmrOneD 281689 Specdb::NmrOneD 281690 Specdb::NmrOneD 281691 Specdb::NmrOneD 281692 Specdb::NmrOneD 281693 Specdb::NmrOneD 281694 Specdb::NmrOneD 281695 Specdb::NmrOneD 281696 Specdb::NmrOneD 281697 Specdb::NmrOneD 281698 Specdb::MsMs 25835 Specdb::MsMs 25836 Specdb::MsMs 25837 Specdb::MsMs 32393 Specdb::MsMs 32394 Specdb::MsMs 32395 GDP-mannose 4,6-dehydratase P0AC88 GM4D_ECOLI gmd http://ecmdb.ca/proteins/P0AC88.xml GDP-L-fucose synthase P32055 FCL_ECOLI fcl http://ecmdb.ca/proteins/P32055.xml Guanosine diphosphate mannose > Water + GDP-4-dehydro-6-deoxy-α-D-mannose PW_R003362 GDP-4-dehydro-6-deoxy-α-D-mannose + NADPH + Hydrogen ion + NADPH > NADP + GDP-β-L-fucose PW_R003363