2.0 2012-07-30 14:54:57 -0600 2015-06-03 17:20:53 -0600 ECMDB21211 M2MDB001619 E-3-Carboxy-2-pentenedioate 6-methyl ester E-3-carboxy-2-pentenedioate 6-methyl ester is catalyzed by trans-aconitate methyltransferase. The trans-aconitate methyltransferase from the bacterium Escherichia coli catalyzes the monomethyl esterification of trans-aconitate and related compounds. Using two-dimensional (1)H/(13)C nuclear magnetic resonance spectroscopy, we show that the methylation is specific to one of the three carboxyl groups and further demonstrate that the product is the 6-methyl ester of trans-aconitate (E-3-carboxy-2-pentenedioate 6-methyl ester). (PMID 11329290) E-3-carboxy-2-pentenedioate 6-methyl ester E-3-Carboxy-2-pentenedioic acid 6-methyl ester Monomethyl-ester-of-trans-aconitate Monomethyl-ester-of-trans-aconitic acid C7H6O6 186.1189 186.016437924 (2E)-3-(methoxycarbonyl)pent-2-enedioate (2E)-3-(methoxycarbonyl)pent-2-enedioate [H]\C(C([O-])=O)=C(\CC([O-])=O)C(=O)OC InChI=1S/C7H8O6/c1-13-7(12)4(2-5(8)9)3-6(10)11/h2H,3H2,1H3,(H,8,9)(H,10,11)/p-2/b4-2+ BRYKYSQCLNCYQW-DUXPYHPUSA-L Cytosol logp 0.21 ALOGPS logs -1.23 ALOGPS solubility 1.30e+01 g/l ALOGPS logp -0.14 ChemAxon pka_strongest_acidic 3.01 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac (2E)-3-(methoxycarbonyl)pent-2-enedioate ChemAxon average_mass 186.1189 ChemAxon mono_mass 186.016437924 ChemAxon smiles [H]\C(C([O-])=O)=C(\CC([O-])=O)C(=O)OC ChemAxon formula C7H6O6 ChemAxon inchi InChI=1S/C7H8O6/c1-13-7(12)4(2-5(8)9)3-6(10)11/h2H,3H2,1H3,(H,8,9)(H,10,11)/p-2/b4-2+ ChemAxon inchikey BRYKYSQCLNCYQW-DUXPYHPUSA-L ChemAxon polar_surface_area 106.56 ChemAxon refractivity 61.67 ChemAxon polarizability 15.55 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 300605 Specdb::NmrOneD 300606 Specdb::NmrOneD 300607 Specdb::NmrOneD 300608 Specdb::NmrOneD 300609 Specdb::NmrOneD 300610 Specdb::NmrOneD 300611 Specdb::NmrOneD 300612 Specdb::NmrOneD 300613 Specdb::NmrOneD 300614 Specdb::NmrOneD 300615 Specdb::NmrOneD 300616 Specdb::NmrOneD 300617 Specdb::NmrOneD 300618 Specdb::NmrOneD 300619 Specdb::NmrOneD 300620 Specdb::NmrOneD 300621 Specdb::NmrOneD 300622 Specdb::NmrOneD 300623 Specdb::NmrOneD 300624 Specdb::MsMs 25478 Specdb::MsMs 25479 Specdb::MsMs 25480 Specdb::MsMs 32036 Specdb::MsMs 32037 Specdb::MsMs 32038 23615417 19951451 C11514 57470 MONOMETHYL-ESTER-OF-TRANS-ACONITATE van 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. 17765195 Cai, H., Strouse, J., Dumlao, D., Jung, M. E., Clarke, S. (2001). "Distinct reactions catalyzed by bacterial and yeast trans-aconitate methyltransferases." Biochemistry 40:2210-2219. 11329290 Trans-aconitate 2-methyltransferase P76145 TAM_ECOLI tam http://ecmdb.ca/proteins/P76145.xml trans-Aconitic acid + S-Adenosylmethionine > E-3-Carboxy-2-pentenedioate 6-methyl ester + S-Adenosylhomocysteine RXN0-2441 S-Adenosylmethionine + trans-Aconitic acid <> S-Adenosylhomocysteine + E-3-Carboxy-2-pentenedioate 6-methyl ester R05763