2.0 2015-09-08 17:49:56 -0600 2015-09-14 16:46:07 -0600 ECMDB24182 M2MDB006299 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-Deoxy-D-arabino-heptulosonate-7-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. DAHPS is involved in the biosynthesis of aromatic amino acids. Maritima DAHP synthase is a metalloenzyme. This report is the first description of a thermophilic eubacterial DAHP synthase. (PMID 12743122) DAHPS(Phe) is a metal-catalyzed oxidation system wherein bound substrate protects active-site residues from oxidative attack catalyzed by bound redox metal cofactor. (PMID 10049398) The first regulatory step in the synthesis of aromatic amino acids is catalyzed by 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAHPS). (PMID 15378531) While several similarities exist between the two enzymatic reactions, classic studies on the Escherichia coli enzymes have established that DAHPS is a metalloenzyme, whereas KDO8PS has no metal requirement. aeolicus KDO8PS is a metalloenzyme in vivo and point to a previously unrecognized relationship between the KDO8PS and DAHPS families. (PMID 10811802) 3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid C7H10O10P 285.122 285.00280426 (4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate (4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate [H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)[C@]([H])(O)CC(=O)C([O-])=O InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/p-3/t3-,5-,6+/m1/s1 PJWIPEXIFFQAQZ-PUFIMZNGSA-K logp -1.59 ALOGPS logs -0.82 ALOGPS solubility 5.11e+01 g/l ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 1.47 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate ChemAxon average_mass 285.122 ChemAxon mono_mass 285.00280426 ChemAxon smiles [H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)[C@]([H])(O)CC(=O)C([O-])=O ChemAxon formula C7H10O10P ChemAxon inchi InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/p-3/t3-,5-,6+/m1/s1 ChemAxon inchikey PJWIPEXIFFQAQZ-PUFIMZNGSA-K ChemAxon polar_surface_area 190.31 ChemAxon refractivity 61.75 ChemAxon polarizability 21.76 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 ChemAxon Chorismate biosynthesis Chorismate is an intermediate in the synthesis of three amino acids: tyrosine, phenylalanine and tryptophan. In addition it is a precursor of folic acid, ubiquinone, menaquinone, and enterochelin. The first reaction in the chorismate pathway is catalyzed by three separate enzymes, all involved in the biosynthesis of Shikimic acid, each of which is subject to feedback inhibition by one of the three amino acids. However, even in the presence of all three amino acids, sufficient enzymatic activity is present to permit synthesis of the other four metabolites synthesized from chorismate because the enzyme subject to regulation by tryptophan cannot be inhibited more than 60 percent. The biosynthesis of chorismate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving Quinate/shikimate dehydrogenase and shikimate dehydrogenase 2. Shikimic acid is phosphorylated by Shikimate kinase 2 into shikimate 3-phosphate. Shikimate 3- phophate and a phosphoenolpyruvic acid are then joined through a 3-phosphoshikimate 1-carboxyvinyltransferase to produce a 5-enoylpyruvyl-shikimate 3-phosphate while releasing a phosphate. This in turns produces our final product Chorismate through a chorismate synthase. PW000816 Metabolic Secondary Metabolites: Shikimate Pathway The biosynthesis of shikimate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving an NADPH driven Quinate/shikimate dehydrogenase or a NADPH driven shikimate dehydrogenase 2. Shikimate can also be transported through a shikimate:H+ symporter. PW000985 Metabolic Specdb::MsMs 25337 Specdb::MsMs 25338 Specdb::MsMs 25339 Specdb::MsMs 31895 Specdb::MsMs 31896 Specdb::MsMs 31897 Phospho-2-dehydro-3-deoxyheptonate aldolase, Trp-sensitive P00887 AROH_ECOLI aroH http://ecmdb.ca/proteins/P00887.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Tyr-sensitive P00888 AROF_ECOLI aroF http://ecmdb.ca/proteins/P00888.xml 3-dehydroquinate synthase P07639 AROB_ECOLI aroB http://ecmdb.ca/proteins/P07639.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive P0AB91 AROG_ECOLI aroG http://ecmdb.ca/proteins/P0AB91.xml D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphate PW_R002910 3-deoxy-D-arabino-heptulosonate-7-phosphate > Phosphate + 3-Dehydroquinate PW_R002911