2.02015-09-08 17:49:56 -06002015-09-14 16:46:07 -0600ECMDB24182M2MDB0062993-deoxy-D-arabino-heptulosonate-7-phosphate3-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 acidC7H10O10P285.122285.00280426(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-])=OInChI=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/s1PJWIPEXIFFQAQZ-PUFIMZNGSA-Klogp-1.59logs-0.82solubility5.11e+01 g/llogp-2.5pka_strongest_acidic1.47pka_strongest_basic-3.3iupac(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoateaverage_mass285.122mono_mass285.00280426smiles[H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)[C@]([H])(O)CC(=O)C([O-])=OformulaC7H10O10PinchiInChI=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/s1inchikeyPJWIPEXIFFQAQZ-PUFIMZNGSA-Kpolar_surface_area190.31refractivity61.75polarizability21.76rotatable_bond_count8acceptor_count9donor_count3physiological_charge-3formal_charge-3Chorismate biosynthesisChorismate 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. PW000816MetabolicSecondary Metabolites: Shikimate PathwayThe 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.PW000985MetabolicSpecdb::MsMs25337Specdb::MsMs25338Specdb::MsMs25339Specdb::MsMs31895Specdb::MsMs31896Specdb::MsMs31897Phospho-2-dehydro-3-deoxyheptonate aldolase, Trp-sensitiveP00887AROH_ECOLIaroHhttp://ecmdb.ca/proteins/P00887.xmlPhospho-2-dehydro-3-deoxyheptonate aldolase, Tyr-sensitiveP00888AROF_ECOLIaroFhttp://ecmdb.ca/proteins/P00888.xml3-dehydroquinate synthaseP07639AROB_ECOLIaroBhttp://ecmdb.ca/proteins/P07639.xmlPhospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitiveP0AB91AROG_ECOLIaroGhttp://ecmdb.ca/proteins/P0AB91.xmlD-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphatePW_R0029103-deoxy-D-arabino-heptulosonate-7-phosphate > Phosphate + 3-DehydroquinatePW_R002911