2.0 2015-09-08 17:49:57 -0600 2016-09-13 16:35:43 -0600 ECMDB24184 M2MDB006301 2,3-Dihydroxybenzoic acid 2-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-Dihydroxybenzoate 2-carboxy-6-hydroxybenzen-1-olate 2-carboxy-6-hydroxybenzenolate logp 0.53 ALOGPS logs -0.77 ALOGPS solubility 2.91e+01 g/l ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 2.56 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 2-carboxy-6-hydroxybenzen-1-olate ChemAxon polar_surface_area 80.59 ChemAxon refractivity 47.83 ChemAxon polarizability 13.39 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Biosynthesis of siderophore group nonribosomal peptides 2,3-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. PW000760 ec01053 Metabolic Enterobactin Biosynthesis Enterobactin is a catecholate siderophore produced almost exclusively by enterobacteria, although it has been reported in some Streptomyces species. It is a cyclic compound made of three units of 2,3-dihydroxybenzoylserine joined in a cyclic structure by lactone linkages (only the δ-cis isomer of the ferric chelate is biologically active). Not only the cyclic molecule, but also the biosynthetic precursor 2,3-dihydroxy-N-benzoylserine and its linear dimer and trimer condensation products are able to transport iron into enterobacteria. Enterobactin is synthesized under iron-deficient conditions and excreted into the environment where it binds Fe(III) with high affinity and specificity. The ferrisiderophore complexes are taken up into the cell by specific transport components. Enterobactin synthesis is divided into two parts: 1) the conversion of chorismate to 2,3-dihydroxybenzoate 2) the synthesis of enterobactin from 2,3-dihydroxybenzoate and L-serine. (EcoCyc) PW002048 Metabolic Specdb::MsMs 24965 Specdb::MsMs 24966 Specdb::MsMs 24967 Specdb::MsMs 31523 Specdb::MsMs 31524 Specdb::MsMs 31525 Isochorismatase P0ADI4 ENTB_ECOLI entB http://ecmdb.ca/proteins/P0ADI4.xml Enterobactin synthase component E P10378 ENTE_ECOLI entE http://ecmdb.ca/proteins/P10378.xml Enterobactin synthase component F P11454 ENTF_ECOLI entF http://ecmdb.ca/proteins/P11454.xml 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase P15047 ENTA_ECOLI entA http://ecmdb.ca/proteins/P15047.xml 4'-phosphopantetheinyl transferase entD P19925 ENTD_ECOLI entD http://ecmdb.ca/proteins/P19925.xml 2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2,3-Dihydroxybenzoic acid + NADH + Hydrogen ion PW_R002454 6 Adenosine triphosphate + 3 L-Serine + 3 2,3-Dihydroxybenzoic acid + 3 L-Serine >6 Adenosine monophosphate + enterobactin +6 Pyrophosphate +3 Hydrogen ion PW_R003389 Adenosine triphosphate + 2,3-Dihydroxybenzoic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acid PW_R005259 Adenosine triphosphate + 2,3-Dihydroxybenzoic acid <> (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate PW_R005260 2,3-Dihydroxybenzoic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate PW_R005979