2.0 2012-05-31 14:20:49 -0600 2015-06-03 17:19:02 -0600 ECMDB12161 M2MDB000824 4-(Glutamylamino) butanoate 4-(Glutamylamino) butanoate is a polyamine that is an intermediate in putrescine degradation . Polyamines (the most common of which are putrescine , spermidine , and spermine ), a group of positively charged small molecules present in virtually all living organisms, have been implicated in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. Although polyamines are clearly necessary for optimal cell growth, a surplus of polyamines can cause inhibition of growth and protein synthesis, and thus a balance is desired between the production and breakdown of polyamines. In putrescine degradation , 4-(Glutamylamino) butanoate is a substrate for gamma-glutamyl-gamma-aminobutyrate hydrolase (puuD) and can be generated from the hydrolysis of gamma-glutamyl-gamma-aminobutyraldehyde. &gamma;-glu-GABA &gamma;-glutamyl-&gamma;-aminobutanoate &gamma;-glutamyl-&gamma;-aminobutanoic acid &gamma;-glutamyl-&gamma;-aminobutyrate &gamma;-glutamyl-&gamma;-aminobutyric acid 4-(Glutamylamino) butanoic acid 4-(Glutamylamino)butanoate 4-(Glutamylamino)butanoic acid 4-(L-g-glutamylamino)Butanoate 4-(L-g-glutamylamino)Butanoic acid 4-(L-gamma-Glutamylamino)butanoate 4-(L-gamma-Glutamylamino)butanoic acid 4-(L-Glutam-5-ylamino)butanoate 4-(L-Glutam-5-ylamino)butanoic acid 4-(L-γ-glutamylamino)Butanoate 4-(L-γ-glutamylamino)Butanoic acid g Glutamyl gaba g-Glu-gaba g-Glutamyl-g aminobutyrate g-Glutamyl-g aminobutyric acid g-Glutamyl-g-aminobutanoate g-Glutamyl-g-aminobutanoic acid g-Glutamyl-g-aminobutyrate g-Glutamyl-g-aminobutyric acid g-Glutamyl-gaba g-L-Glu-g-abu g-L-Glutamyl-g-aminobutyrate g-L-Glutamyl-g-aminobutyric acid Gamma Glutamyl gaba Gamma-Glu-gaba Gamma-Glutamyl-gaba Gamma-Glutamyl-gamma aminobutyrate Gamma-Glutamyl-gamma aminobutyric acid Gamma-Glutamyl-gamma-aminobutanoate Gamma-Glutamyl-gamma-aminobutanoic acid Gamma-Glutamyl-gamma-aminobutyrate Gamma-Glutamyl-gamma-aminobutyric acid Gamma-L-Glu-gamma-abu Gamma-L-Glutamyl-gamma-aminobutyrate Gamma-L-Glutamyl-gamma-aminobutyric acid Glugaba Glutamylgaba N(5)-(3-Carboxypropyl)-L-glutamine γ Glutamyl gaba γ-Glu-gaba γ-Glutamyl-gaba γ-Glutamyl-γ aminobutyrate γ-Glutamyl-γ aminobutyric acid γ-Glutamyl-γ-aminobutanoate γ-Glutamyl-γ-aminobutanoic acid γ-Glutamyl-γ-aminobutyrate γ-Glutamyl-γ-aminobutyric acid γ-L-Glu-γ-abu γ-L-Glutamyl-γ-aminobutyrate γ-L-Glutamyl-γ-aminobutyric acid C9H16N2O5 232.2337 232.105921632 (2S)-2-amino-4-[(3-carboxypropyl)carbamoyl]butanoic acid glugaba 5105-96-4 N[C@@H](CCC(=O)NCCCC(O)=O)C(O)=O InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1 MKYPKZSGLSOGLL-LURJTMIESA-N Solid Cytosol logp -3.37 ALOGPS logs -1.28 ALOGPS solubility 1.21e+01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 2.3 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-[(3-carboxypropyl)carbamoyl]butanoic acid ChemAxon average_mass 232.2337 ChemAxon mono_mass 232.105921632 ChemAxon smiles N[C@@H](CCC(=O)NCCCC(O)=O)C(O)=O ChemAxon formula C9H16N2O5 ChemAxon inchi InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1 ChemAxon inchikey MKYPKZSGLSOGLL-LURJTMIESA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 53.55 ChemAxon polarizability 23.13 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 L-glutamate metabolism There are various ways by which glutamate enters the cytoplasm in E.coli. through a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. There are various ways by which E. coli synthesizes glutamate from L-glutamine or oxoglutaric acid. L-glutamine, introduced into the cytoplasm by glutamine ABC transporter, can either interact with glutaminase resulting in ammonia and L-glutamic acid, or react with oxoglutaric acid, and hydrogen ion through an NADPH driven glutamate synthase resulting in L-glutamic acid. L-glutamic acid is metabolized into L-glutamine by reacting with ammonium through a ATP driven glutamine synthase. L-glutamic acid can also be metabolized into L-aspartic acid by reacting with oxalacetic acid through an aspartate transaminase resulting in n oxoglutaric acid and L-aspartic acid. L-aspartic acid is metabolized into fumaric acid through an aspartate ammonia-lyase. Fumaric acid can be introduced into the cytoplasm through 3 methods: dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, and C4 dicarboxylate / orotate:H+ symporter PW000789 Metabolic arginine metabolism The 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 cycle PW000790 Metabolic ornithine 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. PW000791 Metabolic putrescine degradation II PWY0-1221 Specdb::CMs 2849 Specdb::CMs 39841 Specdb::CMs 175409 Specdb::NmrOneD 95578 Specdb::NmrOneD 95579 Specdb::NmrOneD 95580 Specdb::NmrOneD 95581 Specdb::NmrOneD 95582 Specdb::NmrOneD 95583 Specdb::NmrOneD 95584 Specdb::NmrOneD 95585 Specdb::NmrOneD 95586 Specdb::NmrOneD 95587 Specdb::NmrOneD 95588 Specdb::NmrOneD 95589 Specdb::NmrOneD 95590 Specdb::NmrOneD 95591 Specdb::NmrOneD 95592 Specdb::NmrOneD 95593 Specdb::NmrOneD 95594 Specdb::NmrOneD 95595 Specdb::NmrOneD 95596 Specdb::NmrOneD 95597 Specdb::MsMs 27572 Specdb::MsMs 27573 Specdb::MsMs 27574 Specdb::MsMs 34130 Specdb::MsMs 34131 Specdb::MsMs 34132 Specdb::MsMs 2735708 Specdb::MsMs 2735709 Specdb::MsMs 2735710 Specdb::MsMs 2973396 Specdb::MsMs 2973397 Specdb::MsMs 2973398 HMDB12161 23724570 21865667 C15767 49260 CPD-9000 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). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, 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. 22080510 Gamma-glutamyl-gamma-aminobutyraldehyde dehydrogenase P23883 PUUC_ECOLI puuC http://ecmdb.ca/proteins/P23883.xml Glutamate decarboxylase alpha P69908 DCEA_ECOLI gadA http://ecmdb.ca/proteins/P69908.xml Glutamate decarboxylase beta P69910 DCEB_ECOLI gadB http://ecmdb.ca/proteins/P69910.xml Gamma-glutamyl-gamma-aminobutyrate hydrolase P76038 PUUD_ECOLI puuD http://ecmdb.ca/proteins/P76038.xml 4-(Glutamylamino) butanoate + Water <> gamma-Aminobutyric acid + L-Glutamate R07419 RXN0-3942 gamma-Glutamyl-gamma-butyraldehyde + Water + NADP <> 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH R07418 gamma-Glutamyl-gamma-butyraldehyde + NAD + Water <> 4-(Glutamylamino) butanoate + NADH + Hydrogen ion R07417 gamma-Glutamyl-gamma-butyraldehyde + NADP + Water <> 4-(Glutamylamino) butanoate + NADPH + Hydrogen ion R07418 NAD(P)⁺ + gamma-Glutamyl-gamma-butyraldehyde + Water > 4-(Glutamylamino) butanoate + NAD(P)H + Hydrogen ion RXN0-3922 4-(Glutamylamino) butanoate + Water > gamma-Aminobutyric acid + L-Glutamate RXN0-3942 Gamma-glutamyl-gamma-aminobutyraldehyde + NAD + Water > 4-(Glutamylamino) butanoate + NADH L-Glutamic acid + Hydrogen ion + L-Glutamate > Carbon dioxide + 4-(Glutamylamino) butanoate PW_R005146 4-(γ-glutamylamino)butanal + Water + NADP > 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH + NADPH PW_R002687 4-(Glutamylamino) butanoate + Water > L-Glutamic acid + gamma-Aminobutyric acid + L-Glutamate PW_R002688 gamma-Glutamyl-gamma-butyraldehyde + Water + NADP <>4 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH