2.02012-05-31 13:47:03 -06002015-06-03 15:53:49 -0600ECMDB01180M2MDB000287N2-Succinyl-L-glutamic acid 5-semialdehydeN2-Succinyl-L-glutamic acid 5-semialdehyde is a substrate for Succinate semialdehyde dehydrogenase (mitochondrial) and Ornithine aminotransferase (mitochondrial).N2-Succinyl-L-glutamate 5-semialdehydeN2-succinylglutamate semialdehydeN2-succinylglutamic acid semialdehydeN2-succinylglutamic semialdehydeN2-succinylglutamic-semialdehydeN2SucGluSAN<sup>2</sup>-succinylglutamate semialdehydeN<sup>2</sup>-succinylglutamic semialdehydeN<sup>2</sup>-succinylglutamic-semialdehydeC9H13NO6231.2026231.074287153(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acidOC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=OInChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1XTOKIEIBKARFSZ-LURJTMIESA-NSolidCytosollogp-0.81logs-1.62solubility5.57e+00 g/llogp-1.4pka_strongest_acidic3.38pka_strongest_basic-1.5iupac(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acidaverage_mass231.2026mono_mass231.074287153smilesOC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=OformulaC9H13NO6inchiInChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1inchikeyXTOKIEIBKARFSZ-LURJTMIESA-Npolar_surface_area120.77refractivity50.7polarizability21.38rotatable_bond_count8acceptor_count6donor_count3physiological_charge-2formal_charge0Arginine and proline metabolismec00330arginine metabolismThe metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine.
L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion.
Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid.
L-arginine can be metabolized into succinic acid by two different sets of reactions:
1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and
a succinic acid. The succinic acid is then incorporated in the TCA cycle
2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cyclePW000790Metabolicarginine degradation II (AST pathway)AST-PWYSpecdb::CMs24304Specdb::CMs37961Specdb::CMs147690Specdb::NmrOneD146670Specdb::NmrOneD146671Specdb::NmrOneD146672Specdb::NmrOneD146673Specdb::NmrOneD146674Specdb::NmrOneD146675Specdb::NmrOneD146676Specdb::NmrOneD146677Specdb::NmrOneD146678Specdb::NmrOneD146679Specdb::NmrOneD146680Specdb::NmrOneD146681Specdb::NmrOneD146682Specdb::NmrOneD146683Specdb::NmrOneD146684Specdb::NmrOneD146685Specdb::NmrOneD146686Specdb::NmrOneD146687Specdb::NmrOneD146688Specdb::NmrOneD146689Specdb::MsMs27332Specdb::MsMs27333Specdb::MsMs27334Specdb::MsMs33890Specdb::MsMs33891Specdb::MsMs33892Specdb::MsMs2777396Specdb::MsMs2777397Specdb::MsMs2777398Specdb::MsMs2900673Specdb::MsMs2900674Specdb::MsMs2900675HMDB01180556389690C05932CPD-822Keseler, 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 370:17-25.17765195Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.AN-succinylglutamate 5-semialdehyde dehydrogenaseP76217ASTD_ECOLIastDhttp://ecmdb.ca/proteins/P76217.xmlSuccinylornithine transaminaseP77581ASTC_ECOLIastChttp://ecmdb.ca/proteins/P77581.xmlWater + NAD + N2-Succinyl-L-glutamic acid 5-semialdehyde <>2 Hydrogen ion + NADH + N-Succinyl-L-glutamateR05049alpha-Ketoglutarate + N2-Succinyl-L-ornithine <> L-Glutamate + N2-Succinyl-L-glutamic acid 5-semialdehydeR04217N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water <> N-Succinyl-L-glutamate + NADH + Hydrogen ionR05049N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water > N<SUP>2</SUP>-succinylglutamate + NADH + Hydrogen ionSUCCGLUALDDEHYD-RXNN2-Succinyl-L-ornithine + Oxoglutaric acid > N2-Succinyl-L-glutamic acid 5-semialdehyde + L-GlutamateSUCCORNTRANSAM-RXNN2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water > N-Succinyl-L-glutamate + NADHN2-Succinyl-L-ornithine + Oxoglutaric acid > L-Glutamic acid + N2-Succinyl-L-glutamic acid 5-semialdehyde + L-GlutamatePW_R002680N2-Succinyl-L-glutamic acid 5-semialdehyde + Water + NAD >2 Hydrogen ion + NADH + N2-succinylglutamate + N2-succinylglutamatePW_R002681Water + NAD + N2-Succinyl-L-glutamic acid 5-semialdehyde <>2 Hydrogen ion + NADH + N-Succinyl-L-glutamate