2.02012-07-30 14:54:41 -06002015-06-03 17:20:43 -0600ECMDB21138M2MDB0015472,3-Dihydroxybenzoylserine2,3-dihydroxybenzoylserine is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 2,3-dihydroxybenzoylserine is invovled in Enterobactin degradation. It is a product of the enzyme 2,3-dihydroxybenzoate-serine ligase (EC 6.3.2.14) is an enzyme that catalyzes the chemical reaction ATP + 2,3-dihydroxybenzoate + L-serine
ightleftharpoons products of ATP breakdown + N-(2,3-dihydroxybenzoyl)-L-serine. (PMID 4966114).2,3-Dihydroxy-N-benzoyl-L-serine2,3-dihydroxybenzoylserine2,3DHBSer2-(2,3-Dihydroxybenzoyl)amino-3-hydroxy-propanoate2-(2,3-Dihydroxybenzoyl)amino-3-hydroxy-propanoic acidN-(2,3-Dihydroxybenzoyl)-L-serineC10H11NO6241.1974241.058637089(2S)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acid2,3,-dihydroxybenzoylserine127658-43-9[H][C@@](CO)(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=OInChI=1S/C10H11NO6/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17)/t6-/m0/s1VDTYHTVHFIIEIL-LURJTMIESA-NCytosollogp0.33logs-1.62solubility5.76e+00 g/llogp0.09pka_strongest_acidic2.98pka_strongest_basic-2iupac(2S)-2-[(2,3-dihydroxyphenyl)formamido]-3-hydroxypropanoic acidaverage_mass241.1974mono_mass241.058637089smiles[H][C@@](CO)(NC(=O)C1=C(O)C(O)=CC=C1)C(O)=OformulaC10H11NO6inchiInChI=1S/C10H11NO6/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17)/t6-/m0/s1inchikeyVDTYHTVHFIIEIL-LURJTMIESA-Npolar_surface_area127.09refractivity56.12polarizability22.06rotatable_bond_count4acceptor_count6donor_count5physiological_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.
PW000760ec01053MetabolicSpecdb::CMs1084538Specdb::MsMs25481Specdb::MsMs25482Specdb::MsMs25483Specdb::MsMs32039Specdb::MsMs32040Specdb::MsMs3204125244759133509C0420417455N-23-DIHYDROXYBENZOYL-L-SERINEDBSvan 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 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Enterochelin esteraseP13039FES_ECOLIfeshttp://ecmdb.ca/proteins/P13039.xmlEnterochelin + 3 Water >3 2,3-Dihydroxybenzoylserine +3 Hydrogen ionRXN0-1661Ferric enterobactin + 3 Water >3 2,3-Dihydroxybenzoylserine + Fe3+ +3 Hydrogen ionEnterochelin + Water > Hydrogen ion + 2,3-DihydroxybenzoylserineRXN0-1661(2,3-dihydroxybenzoylserine)<sub>3</sub> + Water 2,3-DihydroxybenzoylserineRXN0-6944