2.02012-08-09 09:16:13 -06002015-09-13 15:15:33 -0600ECMDB21429M2MDB001824N-Acetylglutamic acidN-acetylglutamic acid is an acetylated amino acid. It is involved in arginine biosynthesis and is a substrate for both ArgA and ArgB in E. coli. 2-acetamido-L-Glutaraldehydate2-acetamido-L-Glutaraldehydic acidAc-Glu-OHAcetyl-glutamateAcetyl-glutamic acidAcetyl-L-glutamateAcetyl-L-glutamic acidAcetylglutamateAcetylglutamic acidDL-AcetylglutamateDL-Acetylglutamic acidN-Ac-Glu-OHN-acetyl L-glutamateN-acetyl L-glutamic acidN-Acetyl-DL-glutamateN-Acetyl-DL-glutamic acidN-acetyl-GlutamateN-acetyl-Glutamic acidN-Acetyl-L-glutamateN-Acetyl-L-glutamate-g-semialdehydeN-Acetyl-L-glutamate-gamma-semialdehydeN-Acetyl-L-glutamate-γ-semialdehydeN-Acetyl-L-glutamic acidN-Acetyl-L-glutamic acid-g-semialdehydeN-Acetyl-L-glutamic acid-gamma-semialdehydeN-Acetyl-L-glutamic acid-γ-semialdehydeN-AcetylglutamateN-Acetylglutamic g-semialdehydeN-Acetylglutamic gamma-semialdehydeN-Acetylglutamic γ-semialdehydeN-AcGluC7H11NO5189.1659189.063722467(2S)-2-acetamidopentanedioic acidN-acetyl-L-glutamate1188-37-0CC(=O)NC(CCC(O)=O)C(O)=OInChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)RFMMMVDNIPUKGG-UHFFFAOYSA-NSolidCytoplasmlogp-0.67logs-1.01solubility1.86e+01 g/lmelting_point199 - 201 oClogp-1.1pka_strongest_acidic3.43pka_strongest_basic-1.8iupac(2S)-2-acetamidopentanedioic acidaverage_mass189.1659mono_mass189.063722467smilesCC(=O)NC(CCC(O)=O)C(O)=OformulaC7H11NO5inchiInChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)inchikeyRFMMMVDNIPUKGG-UHFFFAOYSA-Npolar_surface_area103.7refractivity40.73polarizability17.44rotatable_bond_count5acceptor_count5donor_count3physiological_charge-2formal_charge0Arginine and proline metabolismec00330Metabolic pathwayseco01100L-glutamate metabolism IIPW001886Metabolicarginine 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 cyclePW000790Metabolicornithine metabolism
In the ornithine biosynthesis pathway of E. coli, L-glutamate is acetylated to N-acetylglutamate by the enzyme N-acetylglutamate synthase, encoded by the argA gene. The acetyl donor for this reaction is acetyl-CoA. 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 NADPH 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. Ornithine interacts with hydrogen ion through a Ornithine decarboxylase resulting in a carbon dioxide release and a putrescine
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.
PW000791MetabolicSpecdb::CMs1432Specdb::CMs1433Specdb::CMs2636Specdb::CMs30636Specdb::CMs30637Specdb::CMs31710Specdb::CMs31711Specdb::CMs31712Specdb::CMs135578Specdb::CMs143312Specdb::NmrOneD4750Specdb::NmrOneD4751Specdb::NmrOneD146590Specdb::NmrOneD146591Specdb::NmrOneD146592Specdb::NmrOneD146593Specdb::NmrOneD146594Specdb::NmrOneD146595Specdb::NmrOneD146596Specdb::NmrOneD146597Specdb::NmrOneD146598Specdb::NmrOneD146599Specdb::NmrOneD146600Specdb::NmrOneD146601Specdb::NmrOneD146602Specdb::NmrOneD146603Specdb::NmrOneD146604Specdb::NmrOneD146605Specdb::NmrOneD146606Specdb::NmrOneD146607Specdb::NmrOneD146608Specdb::NmrOneD146609Specdb::MsMs46128Specdb::MsMs46129Specdb::MsMs46130Specdb::MsMs146340Specdb::MsMs146341Specdb::MsMs146342Specdb::MsMs437122Specdb::MsMs437123Specdb::MsMs437124Specdb::MsMs437125Specdb::MsMs437126Specdb::MsMs440105Specdb::MsMs445551Specdb::MsMs445552Specdb::MsMs445553Specdb::MsMs445554Specdb::MsMs445555Specdb::MsMs451941Specdb::MsMs2236646Specdb::MsMs2236742Specdb::MsMs2238767Specdb::MsMs2238802Specdb::MsMs2240784Specdb::MsMs2240927Specdb::MsMs2242807Specdb::NmrTwoD2036HMDB01138185180C0062412575N-Acetylglutamic acidvan 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.ASugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21.7952062Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8.2208834Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1.16139832Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12.2342831Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46.1562355hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.http://hmdb.ca/system/metabolites/msds/000/001/023/original/HMDB01138.pdf?1358463345Amino-acid acetyltransferaseP0A6C5ARGA_ECOLIargAhttp://ecmdb.ca/proteins/P0A6C5.xmlAcetylglutamate kinaseP0A6C8ARGB_ECOLIargBhttp://ecmdb.ca/proteins/P0A6C8.xmlN-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADPR02649Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acidR00259L-Glutamic acid + Acetyl-CoA + L-Glutamate > Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetylglutamic acidPW_R002670N-Acetylglutamic acid + Adenosine triphosphate + N-Acetylglutamic acid > Adenosine diphosphate + N-Acetyl-L-glutamyl 5-phosphate + ADPPW_R002671Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acidPW_R005149Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acidN-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP