2.02012-05-31 10:26:32 -06002015-09-13 12:56:08 -0600ECMDB00397M2MDB0001342-Pyrocatechuic acid2-pyrocatechuic acid, also known as 2,3-Dihydroxybenzoic acid, is a member of the chemical class known as Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. 2,3-Dihydroxybenzoic acid is a colorless solid that occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine. (Wikipedia) In E. coli K-12, 2-pyrocatechuic acid is involved in biosynthesis of siderophore group nonribosomal peptides. (KEGG)2,3-Dihydroxybenzoate2,3-Dihydroxybenzoic acid2-Pyrocatechuate2-Pyrocatechuic acid3-Hydroxysalicylate3-Hydroxysalicylic acidCatechol-3-carboxylateCatechol-3-carboxylic acidCatecholcarboxylateCatecholcarboxylic acidDHBADOBKO-PyrocatechuateO-Pyrocatechuic acidPyrocatechuatePyrocatechuic acidC7H6O4154.1201154.026608682,3-dihydroxybenzoic acid2,3-dihydroxy-benzoic acid303-38-8OC(=O)C1=CC=CC(O)=C1OInChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)GLDQAMYCGOIJDV-UHFFFAOYSA-NCytosollogp1.42logs-1.35solubility6.88e+00 g/llogp1.67pka_strongest_acidic2.56pka_strongest_basic-6.3iupac2,3-dihydroxybenzoic acidaverage_mass154.1201mono_mass154.02660868smilesOC(=O)C1=CC=CC(O)=C1OformulaC7H6O4inchiInChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)inchikeyGLDQAMYCGOIJDV-UHFFFAOYSA-Npolar_surface_area77.76refractivity37.28polarizability13.71rotatable_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.
PW000760ec01053MetabolicBenzoate degradation via hydroxylationec003621,4-Dichlorobenzene degradationec00627Microbial metabolism in diverse environmentsec011202,3-dihydroxybenzoate biosynthesis2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. Chorismate is a key intermediate and branch point in the biosynthesis of many aromatic compounds.
The biosynthesis of 2,3-dihydroxybenzoate from chorismate is catalyzed by three enzymes EntC, EntB, and EntA. 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.
PW000751Metabolicenterobactin biosynthesisENTBACSYN-PWY2,3-dihydroxybenzoate biosynthesisPWY-5901Specdb::CMs546Specdb::CMs1391Specdb::CMs5646Specdb::CMs30417Specdb::CMs31139Specdb::CMs31798Specdb::CMs37497Specdb::CMs137174Specdb::CMs144908Specdb::CMs1060433Specdb::CMs1060435Specdb::CMs1060437Specdb::CMs1060438Specdb::CMs1060440Specdb::CMs1060442Specdb::CMs1060444Specdb::CMs1060445Specdb::CMs1060447Specdb::CMs1060449Specdb::CMs1060451Specdb::CMs1060452Specdb::CMs1060454Specdb::NmrOneD143710Specdb::NmrOneD143711Specdb::NmrOneD143712Specdb::NmrOneD143713Specdb::NmrOneD143714Specdb::NmrOneD143715Specdb::NmrOneD143716Specdb::NmrOneD143717Specdb::NmrOneD143718Specdb::NmrOneD143719Specdb::NmrOneD143720Specdb::NmrOneD143721Specdb::NmrOneD143722Specdb::NmrOneD143723Specdb::NmrOneD143724Specdb::NmrOneD143725Specdb::NmrOneD143726Specdb::NmrOneD143727Specdb::NmrOneD143728Specdb::NmrOneD143729Specdb::MsMs603Specdb::MsMs604Specdb::MsMs605Specdb::MsMs240037Specdb::MsMs240038Specdb::MsMs240039Specdb::MsMs242092Specdb::MsMs242093Specdb::MsMs242094Specdb::MsMs439732Specdb::MsMs440138Specdb::MsMs449821Specdb::MsMs449822Specdb::MsMs2255333Specdb::MsMs2257188Specdb::MsMs2257381Specdb::MsMs2259225Specdb::MsMs2259355Specdb::MsMs2365120Specdb::MsMs2365121Specdb::MsMs2365122Specdb::MsMs2597929Specdb::MsMs2597930Specdb::MsMs2597931Specdb::NmrTwoD1297HMDB0039718C00196180262-3-DIHYDROXYBENZOATEDBHKeseler, I. 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Bangladesh Med Res Counc Bull. 1994 Dec;20(3):104-16.7748148http://hmdb.ca/system/metabolites/msds/000/000/316/original/HMDB00397.pdf?1358461713Enterobactin synthase component EP10378ENTE_ECOLIentEhttp://ecmdb.ca/proteins/P10378.xml2,3-dihydro-2,3-dihydroxybenzoate dehydrogenaseP15047ENTA_ECOLIentAhttp://ecmdb.ca/proteins/P15047.xmlBlue copper oxidase cueOP36649CUEO_ECOLIcueOhttp://ecmdb.ca/proteins/P36649.xml2-Pyrocatechuic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + PyrophosphateDHBAMPLIG-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 ionR015052-Pyrocatechuic acid + Oxygen > Hydrogen ion + 2-CarboxymuconateRXN0-2943NAD + (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate > Hydrogen ion + NADH + 2-Pyrocatechuic acidDHBDEHYD-RXNAdenosine triphosphate + L-Serine + 2-Pyrocatechuic acid > Hydrogen ion + Pyrophosphate + Adenosine monophosphate + EnterochelinENTMULTI-RXN2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2-Pyrocatechuic acid + NADHAdenosine triphosphate + 2-Pyrocatechuic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acidAdenosine triphosphate + 2-Pyrocatechuic acid <> Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acidR01504 2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2-Pyrocatechuic acid + NADH + Hydrogen ionPW_R002423Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture138.0uM0.037 oCK12 NCM3722Mid-Log Phase5520000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolShake flask and filter culture414.0uM0.037 oCK12 NCM3722Mid-Log Phase16560000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateShake flask and filter culture274.0uM0.037 oCK12 NCM3722Mid-Log Phase10960000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621