2.0 2012-05-31 13:01:16 -0600 2015-10-15 16:13:37 -0600 ECMDB00805 M2MDB000187 Pyrrolidonecarboxylic acid Pyrrolidonecarboxylic acid is a member of the chemical class known as Pyrrolidine Carboxylic Acids and Derivatives. These are compounds containing a pyrrolidine ring which bears a carboxylic acid or a derivative thereof. 2-Pyrrolidone-5-carboxylic acid (PCA) is a cyclic derivative of glutamic acid, and has been found in E. coli beta-galactosidase. It is produced by gamma-glutamyl phosphate reductase (glutamate semialdehyde dehydrogenase) via glutamic acid 5-semidaldehyde [PMID: 7034716]. (+)-2-Pyrrolidone-5-carboxylate (+)-2-Pyrrolidone-5-carboxylic acid (+)-Pyroglutamate (+)-Pyroglutamic acid (2R)-2-Carboxy-5-pyrrolidinone (R)-(+)-2-Pyrrolidone-5-carboxylate (R)-(+)-2-Pyrrolidone-5-carboxylic acid (R)-2-Pyrrolidone-5-carboxylate (R)-2-Pyrrolidone-5-carboxylic acid (R)-5-Oxopyrrolidine-2-carboxylate (R)-5-Oxopyrrolidine-2-carboxylic acid 5-Oxo-D-proline D-2-Pyrrolidone-5-carboxylic D-5-Pyrrolidone-2-carboxylate D-5-Pyrrolidone-2-carboxylic acid D-Pyroglutamate D-Pyroglutamic acid Pyrrolidonecarboxylate C5H7NO3 129.114 129.042593095 (2R)-5-oxopyrrolidine-2-carboxylic acid 5-oxo-D-proline 4042-36-8 OC(=O)[C@@H]1CCC(=O)N1 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 ODHCTXKNWHHXJC-VKHMYHEASA-N Solid Cytoplasm Periplasm logp -1.01 ALOGPS logs 0.07 ALOGPS solubility 1.51e+02 g/l ALOGPS melting_point 155 - 162 oC logp -0.89 ChemAxon pka_strongest_acidic 3.61 ChemAxon pka_strongest_basic -1.8 ChemAxon iupac (2R)-5-oxopyrrolidine-2-carboxylic acid ChemAxon average_mass 129.114 ChemAxon mono_mass 129.042593095 ChemAxon smiles OC(=O)[C@@H]1CCC(=O)N1 ChemAxon formula C5H7NO3 ChemAxon inchi InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 ChemAxon inchikey ODHCTXKNWHHXJC-VKHMYHEASA-N ChemAxon polar_surface_area 66.4 ChemAxon refractivity 28.09 ChemAxon polarizability 11.42 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon D-Glutamine and D-glutamate metabolism L-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine. L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter. L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase. D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase. PW000769 ec00471 Metabolic Specdb::MsMs 28877 Specdb::MsMs 28878 Specdb::MsMs 28879 Specdb::MsMs 35435 Specdb::MsMs 35436 Specdb::MsMs 35437 HMDB00805 388752 C02237 16924 CPD-656 Keseler, 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). 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"Proline biosynthesis in Escherichia coli. Stoichiometry and end-product identification of the reaction catalysed by glutamate semialdehyde dehydrogenase." Biochem J 197:269-274. 7034716 Gamma-glutamyl phosphate reductase P07004 PROA_ECOLI proA http://ecmdb.ca/proteins/P07004.xml 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 197.0 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 788000 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776