2.02012-05-31 13:01:16 -06002015-10-15 16:13:37 -0600ECMDB00805M2MDB000187Pyrrolidonecarboxylic acidPyrrolidonecarboxylic 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 acid5-Oxo-D-prolineD-2-Pyrrolidone-5-carboxylicD-5-Pyrrolidone-2-carboxylateD-5-Pyrrolidone-2-carboxylic acidD-PyroglutamateD-Pyroglutamic acidPyrrolidonecarboxylateC5H7NO3129.114129.042593095(2R)-5-oxopyrrolidine-2-carboxylic acid5-oxo-D-proline4042-36-8OC(=O)[C@@H]1CCC(=O)N1InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1ODHCTXKNWHHXJC-VKHMYHEASA-NSolidCytoplasmPeriplasmlogp-1.01logs0.07solubility1.51e+02 g/lmelting_point155 - 162 oClogp-0.89pka_strongest_acidic3.61pka_strongest_basic-1.8iupac(2R)-5-oxopyrrolidine-2-carboxylic acidaverage_mass129.114mono_mass129.042593095smilesOC(=O)[C@@H]1CCC(=O)N1formulaC5H7NO3inchiInChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1inchikeyODHCTXKNWHHXJC-VKHMYHEASA-Npolar_surface_area66.4refractivity28.09polarizability11.42rotatable_bond_count1acceptor_count3donor_count2physiological_charge-1formal_charge0D-Glutamine and D-glutamate metabolismL-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.
PW000769ec00471MetabolicSpecdb::MsMs28877Specdb::MsMs28878Specdb::MsMs28879Specdb::MsMs35435Specdb::MsMs35436Specdb::MsMs35437HMDB00805388752C0223716924CPD-656Keseler, 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). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van 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 370:17-25.17765195Ishii, 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 316:593-597.17379776Hayzer, D. J., Leisinger, T. (1981). "Proline biosynthesis in Escherichia coli. Stoichiometry and end-product identification of the reaction catalysed by glutamate semialdehyde dehydrogenase." Biochem J 197:269-274.7034716Gamma-glutamyl phosphate reductaseP07004PROA_ECOLIproAhttp://ecmdb.ca/proteins/P07004.xml48 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h197.0uM0.037 oCBW25113Stationary Phase, glucose limited7880000Ishii, 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