2.0 2012-05-31 14:24:15 -0600 2015-06-03 17:19:10 -0600 ECMDB20039 M2MDB000888 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate 2-dehydro-3-deoxy-D-arabino-heptonate 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) 2-Dahp 2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate 2-Dehydro-3-deoxy-D-arabino-heptonic acid 7-phosphate 2-dehydro-3-Deoxy-D-arabino-heptonic acid 7-phosphoric acid 2-Dehydro-3-deoxy-D-arabino-heptulosonate-7-phosphate 2-Dehydro-3-deoxy-D-arabino-heptulosonic acid-7-phosphate 2-dehydro-3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid 3-Deoxy-7-O-phosphono-D-arabino-hept-2-ulosonate 3-Deoxy-7-O-phosphono-D-arabino-hept-2-ulosonic acid 3-Deoxy-arabino-heptulonate 7-phosphate 3-Deoxy-arabino-heptulonic acid 7-phosphate 3-Deoxy-arabino-heptulonic acid 7-phosphoric acid 3-Deoxy-arabino-heptulosonate 7-phosphate 3-Deoxy-arabino-heptulosonate-7-P 3-Deoxy-arabino-heptulosonic acid 7-phosphate 3-Deoxy-arabino-heptulosonic acid 7-phosphoric acid 3-Deoxy-arabino-heptulosonic acid-7-P 3-Deoxy-D-arabino-hept-2-ulosonate 7-phosphate 3-Deoxy-D-arabino-hept-2-ulosonate-7-phosphate 3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphate 3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphoric acid 3-Deoxy-D-arabino-hept-2-ulosonic acid-7-phosphoric acid 3-Deoxy-D-arabino-heptulosonate 7-phosphate 3-Deoxy-D-arabino-heptulosonate-7-P 3-Deoxy-D-arabino-heptulosonate-7-phosphate 3-Deoxy-D-arabino-heptulosonic acid 7-phosphate 3-Deoxy-D-arabino-heptulosonic acid 7-phosphoric acid 3-Deoxy-D-arabino-heptulosonic acid-7-P 3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid 3-Deoxyarabinoheptulosonate-7-phosphate 3-Deoxyarabinoheptulosonic acid-7-phosphoric acid 3DAH7P 7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonate 7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid 7-Phospho-2-keto-3-deoxy-D-arabinoheptonate 7-Phospho-2-keto-3-deoxy-D-arabinoheptonic acid DAHP C7H13O10P 288.1459 288.024633148 (4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid DAHP 2627-73-8 O[C@H](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)/t3-,5-,6+/m1/s1 PJWIPEXIFFQAQZ-PUFIMZNGSA-N Cytosol logp -2.47 ALOGPS logs -1.31 ALOGPS solubility 1.41e+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-(phosphonooxy)heptanoic acid ChemAxon average_mass 288.1459 ChemAxon mono_mass 288.024633148 ChemAxon smiles O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)CC(=O)C(O)=O ChemAxon formula C7H13O10P 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)/t3-,5-,6+/m1/s1 ChemAxon inchikey PJWIPEXIFFQAQZ-PUFIMZNGSA-N ChemAxon polar_surface_area 181.82 ChemAxon refractivity 53.15 ChemAxon polarizability 22.37 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Metabolic pathways eco01100 3-dehydroquinate biosynthesis I PWY-6164 Specdb::CMs 3125 Specdb::NmrOneD 272258 Specdb::NmrOneD 272259 Specdb::NmrOneD 272260 Specdb::NmrOneD 272261 Specdb::NmrOneD 272262 Specdb::NmrOneD 272263 Specdb::NmrOneD 272264 Specdb::NmrOneD 272265 Specdb::NmrOneD 272266 Specdb::NmrOneD 272267 Specdb::NmrOneD 272268 Specdb::NmrOneD 272269 Specdb::NmrOneD 272270 Specdb::NmrOneD 272271 Specdb::NmrOneD 272272 Specdb::NmrOneD 272273 Specdb::NmrOneD 272274 Specdb::NmrOneD 272275 Specdb::NmrOneD 272276 Specdb::NmrOneD 272277 Specdb::MsMs 24995 Specdb::MsMs 24996 Specdb::MsMs 24997 Specdb::MsMs 31553 Specdb::MsMs 31554 Specdb::MsMs 31555 Specdb::MsMs 3608011 Specdb::MsMs 3608012 Specdb::MsMs 3608013 Specdb::MsMs 3608014 Specdb::MsMs 3608015 Specdb::MsMs 3608016 160647 80 C04691 18150 3-DEOXY-D-ARABINO-HEPTULOSONATE-7-P Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Duewel, H. S., Woodard, R. W. (2000). "A metal bridge between two enzyme families. 3-deoxy-D-manno-octulosonate-8-phosphate synthase from Aquifex aeolicus requires a divalent metal for activity." J Biol Chem 275:22824-22831. 10811802 Park, O. K., Bauerle, R. (1999). "Metal-catalyzed oxidation of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli: inactivation and destabilization by oxidation of active-site cysteines." J Bacteriol 181:1636-1642. 10049398 Wu, J., Howe, D. L., Woodard, R. W. (2003). "Thermotoga maritima 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthase: the ancestral eubacterial DAHP synthase?" J Biol Chem 278:27525-27531. 12743122 Xu, J., Hu, C., Shen, S., Wang, W., Jiang, P., Huang, W. (2004). "Requirement of the N-terminus for dimer formation of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate synthase AroG of Escherichia coli." J Basic Microbiol 44:400-406. 15378531 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 <> 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate R01826 DAHPSYN-RXN 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <> 3-Dehydroquinate + Phosphate R03083 3-DEHYDROQUINATE-SYNTHASE-RXN 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > Phosphate + 3-Dehydroquinate 3-DEHYDROQUINATE-SYNTHASE-RXN 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > 3-Dehydroquinate + Inorganic phosphate Phosphoenolpyruvic acid + D-Erythrose 4-phosphate + Water > 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Inorganic phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate