2.02012-05-31 14:22:38 -06002015-06-03 17:19:07 -0600ECMDB20009M2MDB000858(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate is a member of the chemical class known as Beta Hydroxy Acids and Derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. It is involved in siderophore biosynthesis and enterobactin biosynthesis.(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoic acid2,3-Dihydro-2,3-dihydroxybenzoate2,3-Dihydro-2,3-dihydroxybenzoic acid2,3-Dihydroxy-2,3-dihydrobenzoate2,3-Dihydroxy-2,3-dihydrobenzoic acid5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylate5,6-Dihydroxycyclohexa-1,3-diene-1-carboxylic acidDihydro-dioh-benzoateDihydro-dioh-benzoic acidC7H8O4156.136156.042258744(5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid(5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid[H][C@]1(O)C=CC=C(C(O)=O)[C@]1([H])OInChI=1S/C7H8O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,5-6,8-9H,(H,10,11)/t5-,6-/m0/s1INCSWYKICIYAHB-WDSKDSINSA-NCytoplasmPeriplasmlogp-0.33logs-0.23solubility9.20e+01 g/llogp-0.77pka_strongest_acidic4.12pka_strongest_basic-3.4iupac(5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acidaverage_mass156.136mono_mass156.042258744smiles[H][C@]1(O)C=CC=C(C(O)=O)[C@]1([H])OformulaC7H8O4inchiInChI=1S/C7H8O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,5-6,8-9H,(H,10,11)/t5-,6-/m0/s1inchikeyINCSWYKICIYAHB-WDSKDSINSA-Npolar_surface_area77.76refractivity38.56polarizability14.15rotatable_bond_count1acceptor_count4donor_count3physiological_charge-1formal_charge0Biosynthesis of siderophore group nonribosomal peptides2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate.
The biosynthesis of 2,3-dihydroxybenzoate starts from chorismate being synthesized into isochorismate through isochorismate synthase entC. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.This compound then interacts with L-serine and ATP through enterobactin synthase protein complex resulting in the production of enterobactin. Enterobactin is exported into the periplasmic space through the enterobactin exporter entS. The compound is the export to the environment through the outer membrane protein TolC. In the environment enterobactin reacts with iron to produce Ferric enterobactin. This compound is imported into the periplasmic space through a ferric enterobactin outermembrane transport complex. The compound then enters the cytoplasm through a ferric enterobactin ABC transporter.Once inside the cytoplasm, ferric enterobactin spontaneously releases the iron ion from the enterobactin.
PW000760ec01053Metabolic2,3-dihydroxybenzoate biosynthesisPWY-5901Specdb::CMs1087674Specdb::NmrOneD345268Specdb::NmrOneD345269Specdb::NmrOneD345270Specdb::NmrOneD345271Specdb::NmrOneD345272Specdb::NmrOneD345273Specdb::NmrOneD345274Specdb::NmrOneD345275Specdb::NmrOneD345276Specdb::NmrOneD345277Specdb::NmrOneD345278Specdb::NmrOneD345279Specdb::NmrOneD345280Specdb::NmrOneD345281Specdb::NmrOneD345282Specdb::NmrOneD345283Specdb::NmrOneD345284Specdb::NmrOneD345285Specdb::NmrOneD345286Specdb::NmrOneD345287Specdb::MsMs27368Specdb::MsMs27369Specdb::MsMs27370Specdb::MsMs33926Specdb::MsMs33927Specdb::MsMs3392838139753C0417115941DIHYDRO-DIOH-BENZOATEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510IsochorismataseP0ADI4ENTB_ECOLIentBhttp://ecmdb.ca/proteins/P0ADI4.xml2,3-dihydro-2,3-dihydroxybenzoate dehydrogenaseP15047ENTA_ECOLIentAhttp://ecmdb.ca/proteins/P15047.xmlWater + Isochorismate <> (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + Pyruvic acidR03037ISOCHORMAT-RXN(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD + 2,3-Dihydro-2,3-dihydroxybenzoic acid <> 2-Pyrocatechuic acid + Hydrogen ion + NADHR01505DHBDEHYD-RXN(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD <> 2-Pyrocatechuic acid + NADH + Hydrogen ionR01505NAD + (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate > Hydrogen ion + NADH + 2-Pyrocatechuic acidDHBDEHYD-RXN