1-Pyrroline-5-carboxylic acid

changed 477199125 Delta-1-pyrroline-5-carboxylic acid.svg 3,4-Dihydro-2H-pyrrole-2-carboxylic acid 1-Pyrroline-5-carboxylic acidδ-1-Pyrroline-5-carboxylic acidP5C correct chemspider correct EBI 1372 1159 correct kegg C04322 1/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8) DWAKNKKXGALPNW-UHFFFAOYAB O=C(O)C1/N=C\CC1 correct EBI 1161508 correct chemspider 1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8) correct chemspider DWAKNKKXGALPNW-UHFFFAOYSA-N changed ?? 2906-39-0 correct FDA 52TNU46DHL 1196 C1CC(N=C1)C(=O)O Delta-1-pyrroline-5-carboxylate C5H7NO2 113.115 g/mol 1.82/6.07 https://chemicalize.com/app/calculation/pyrroline-5-carboxylate computed by Chemicalize from ChemAxon 1-Pyrroline-5-carboxylic acid (systematic name 3,4-dihydro-2H-pyrrole-2-carboxylic acidhttps://pubchem.ncbi.nlm.nih.gov/compound/1196 3,4-Dihydro-2H-pyrrole-2-carboxylic acid PubChem pubchem.ncbi.nlm.nih.gov en 2020-01-23) is a cyclic imino acid. Its conjugate base and anion is 1-pyrroline-5-carboxylate (P5C). In solution, P5C is in spontaneous equilibrium with glutamate-5-semialdehyde (GSA).Heacock Anne M. Williams Irene H. Frank Leonard H. Adams Elijah 1975-04-01 Δ1-Pyrroline-5-carboxylate and Δ1-pyrroline-3-hydroxy-5-carboxylate: Chromatography on the amino acid analyzer Analytical Biochemistry en 64 2 593–600 10.1016/0003-2697(75)90472-8 236687 0003-2697 Biochemistry The stereoisomer (S)-1-pyrroline-5-carboxylate (also referred to as L-P5C) is an intermediate metabolite in the biosynthesis and degradation of proline and arginine.Bertolo Robert F. Burrin Douglas G. 2008-10-01 Comparative Aspects of Tissue Glutamine and Proline Metabolism The Journal of Nutrition en 138 10 2032S–2039S 10.1093/jn/138.10.2032S 18806120 0022-3166 freeQamar Aarzoo Mysore Kirankumar Senthil-Kumar Muthappa 2015 Role of proline and pyrroline-5-carboxylate metabolism in plant defense against invading pathogens Frontiers in Plant Science en 6 503 10.3389/fpls.2015.00503 4491715 26217357 2015FrPS....6..503Q 1664-462X freeWinter Gudrun Todd Christopher D. Trovato Maurizio Forlani Giuseppe Funck Dietmar 2015 Physiological implications of arginine metabolism in plants Frontiers in Plant Science en 6 534 10.3389/fpls.2015.00534 26284079 4520006 2015FrPS....6..534W 1664-462X free In prokaryotic proline biosynthesis, GSA is synthesized from γ-glutamyl phosphate by the enzyme γ-glutamyl phosphate reductase. Baich A The biosynthesis of proline in Escherichia coli: phosphate-dependent glutamate -semialdehyde dehydrogenase (NADP), the second enzyme in the pathway Biochimica et Biophysica Acta 244 1 129–34 July 1971 4399189 10.1016/0304-4165(71)90129-2 55% Q27102623 L-γ-glutamyl phosphate + NADPH reversible Pi H+ H+ Pi Q2823261 L-glutamate-5-semialdehyde + NADP+ In most eukaryotes, GSA is synthesised from the amino acid glutamate by the bifunctional enzyme 1-pyrroline-5-carboxylate synthase (P5CS). The human P5CS is encoded by the ALDH18A1 gene.Liu G, Maunoury C, Kamoun P, Aral B Oct 1996 Assignment of the human gene encoding the delta 1-pyrroline-5-carboxylate synthetase (P5CS) to 10q24.3 by in situ hybridization Genomics 37 1 145–6 10.1006/geno.1996.0535 8921385https://www.ncbi.nlm.nih.gov/gene?Db=gene&Cmd=ShowDetailView&TermToSearch=5832 Entrez Gene: ALDH18A1 aldehyde dehydrogenase 18 family, member A1 The enzyme pyrroline-5-carboxylate reductase converts L-P5C into proline. Smith ME Greenberg DM Characterization of an enzyme reducing pyrroline-5-carboxylate to proline Nature 1956 177 4520 1130 10.1038/1771130a0 13334497 1956Natur.177.1130S 4298013 free 45% Q27105294 L-P5C + NADH reversible H+ H+ Q20035886 L-proline + NAD+ In proline degradation, the enzyme proline dehydrogenase produces P5C from proline, and the enzyme 1-pyrroline-5-carboxylate dehydrogenase converts GSA to glutamate. In many prokaryotes, proline dehydrogenase and P5C dehydrogenase form a bifunctional enzyme that prevents the release of P5C during proline degradation.Liu Li-Kai Becker Donald F. Tanner John J. 2017-10-15 Structure, function, and mechanism of proline utilization A (PutA) Archives of Biochemistry and Biophysics Flavoproteins: Beyond the Classical Paradigms en 632 142–157 10.1016/j.abb.2017.07.005 28712849 5650515 0003-9861 A reciprocal regulation of delta 1-pyrroline-5-carboxylate synthetase (P5CS) and proline dehydrogenase genes controls proline levels during and after osmotic stress in plants proportional to the level of proline.Verma D.P.S December 1996 Reciprocal regulation of delta 1-pyrroline-5-carboxylate synthetase and proline dehydrogenase genes controls proline levels during and after osmotic stress in plants Molecular Genetics 253 3 334–341 10.1007/pl00008600 9003320 This allows an optimum level of proline to be produced from reduced nitrogen to control osmotic stress. References Category:Pyrrolines Category:Carboxylic acids