2.0 2012-05-31 14:21:08 -0600 2015-06-03 17:19:03 -0600 ECMDB12230 M2MDB000830 gamma-Glutamyl-L-putrescine Gamma-glutamyl-L-putrescine is involved in the putrescine degradation pathway. &gamma;-Glu-Put &gamma;-glutamylputrescine g-Glu-put g-Glutamyl-L-putrescine g-Glutamyl-putrescine g-Glutamylputrescine g-L Glutamylputrescine g-L-Glutamylputrescine Gamma-Glu-put Gamma-Glutamyl-putrescine Gamma-Glutamylputrescine Gamma-L Glutamylputrescine Gamma-L-Glutamylputrescine N-(4-Aminobutyl)-L-glutamine γ-Glu-put γ-Glutamyl-L-putrescine γ-Glutamyl-putrescine γ-Glutamylputrescine γ-L Glutamylputrescine γ-L-Glutamylputrescine C9H19N3O3 217.2655 217.142641489 (2S)-2-amino-4-[(4-aminobutyl)carbamoyl]butanoic acid gamma-L-glutamylputrescine NCCCCNC(=O)CC[C@H](N)C(O)=O InChI=1S/C9H19N3O3/c10-5-1-2-6-12-8(13)4-3-7(11)9(14)15/h7H,1-6,10-11H2,(H,12,13)(H,14,15)/t7-/m0/s1 WKGTVHGVLRCTCF-ZETCQYMHSA-N Solid Cytosol logp -3.42 ALOGPS logs -1.09 ALOGPS solubility 1.77e+01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 2.24 ChemAxon pka_strongest_basic 10 ChemAxon iupac (2S)-2-amino-4-[(4-aminobutyl)carbamoyl]butanoic acid ChemAxon average_mass 217.2655 ChemAxon mono_mass 217.142641489 ChemAxon smiles NCCCCNC(=O)CC[C@H](N)C(O)=O ChemAxon formula C9H19N3O3 ChemAxon inchi InChI=1S/C9H19N3O3/c10-5-1-2-6-12-8(13)4-3-7(11)9(14)15/h7H,1-6,10-11H2,(H,12,13)(H,14,15)/t7-/m0/s1 ChemAxon inchikey WKGTVHGVLRCTCF-ZETCQYMHSA-N ChemAxon polar_surface_area 118.44 ChemAxon refractivity 55.47 ChemAxon polarizability 23.61 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Metabolic pathways eco01100 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 Several metabolic pathways for putrescine degradation as a source of nitrogen for E. coli K-12 are known. The first putrescine degradation pathway was found in in 1985. That pathway is dedicated to the degradation of intracellular putrescine. A second pathway was found in E. coli K-12 twenty years later. This pathway seems to be dedicated to the degradation of extracellular putrescine. The pathway was discovered following the discovery of a cluster of seven unassigned genes on the E. coli K-12 chromosome. In addition to a putrescine transporter, encoded by the puuP gene, the cluster contains four genes that encode the enzymes involved in this pathway, and two additional genes (puuE and puuR) that encode an enzyme involved in the catabolism of GABA (see superpathway of 4-aminobutanoate degradation) and a regulator. In this pathway, putrescine is γ-glutamylated at the expense of an ATP molecule. The resulting γ-glutamyl-putrescine is oxidized to γ-glutamyl-γ-aminobutyraldehyde, which is then dehydrogenated into 4-(glutamylamino) butanoate. In the last step, the γ-glutamyl group is removed by hydrolysis, generating 4-aminobutyrate. The key difference between this pathway and putrescine degradation I is the γ-glutamylation of putrescine. In the other pathway, putrescine is degraded directly to 4-amino-butanal. Wild type E. coli cells are unable to utilize putrescine as the sole source of carbon at temperatures above 30°C. It is possible to select for mutants that possess this ability; these mutants contain elevated levels of the enzymes in this pathway. (EcoCyc) PW002054 Metabolic putrescine degradation II PWY0-1221 Specdb::CMs 39876 Specdb::CMs 64428 Specdb::CMs 132695 Specdb::CMs 140429 Specdb::NmrOneD 151550 Specdb::NmrOneD 151551 Specdb::NmrOneD 151552 Specdb::NmrOneD 151553 Specdb::NmrOneD 151554 Specdb::NmrOneD 151555 Specdb::NmrOneD 151556 Specdb::NmrOneD 151557 Specdb::NmrOneD 151558 Specdb::NmrOneD 151559 Specdb::NmrOneD 151560 Specdb::NmrOneD 151561 Specdb::NmrOneD 151562 Specdb::NmrOneD 151563 Specdb::NmrOneD 151564 Specdb::NmrOneD 151565 Specdb::NmrOneD 151566 Specdb::NmrOneD 151567 Specdb::NmrOneD 151568 Specdb::NmrOneD 151569 Specdb::MsMs 24974 Specdb::MsMs 24975 Specdb::MsMs 24976 Specdb::MsMs 31532 Specdb::MsMs 31533 Specdb::MsMs 31534 Specdb::MsMs 2828705 Specdb::MsMs 2828706 Specdb::MsMs 2828707 Specdb::MsMs 2853001 Specdb::MsMs 2853002 Specdb::MsMs 2853003 HMDB12230 20841830 20148392 C15699 GAMMA-GLUTAMYL-PUTRESCINE 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-glutamylputrescine oxidoreductase P37906 PUUB_ECOLI puuB http://ecmdb.ca/proteins/P37906.xml Gamma-glutamylputrescine synthetase P78061 PUUA_ECOLI puuA http://ecmdb.ca/proteins/P78061.xml Adenosine triphosphate + L-Glutamate + Putrescine + Ethylenediamine <> ADP + gamma-Glutamyl-L-putrescine + Hydrogen ion + Phosphate R07414 RXN0-3901 gamma-Glutamyl-L-putrescine + Water + Oxygen > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + Ammonium RXN0-3921 Adenosine triphosphate + L-Glutamate + Putrescine <> ADP + Phosphate + gamma-Glutamyl-L-putrescine R07414 gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxide R07415 Putrescine + L-Glutamate + Adenosine triphosphate > Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP + Phosphate RXN0-3901 Adenosine triphosphate + L-Glutamate + Putrescine > ADP + Inorganic phosphate + gamma-Glutamyl-L-putrescine gamma-Glutamyl-L-putrescine + Water + Oxygen > Gamma-glutamyl-gamma-aminobutyraldehyde + Ammonia + Hydrogen peroxide Putrescine + Adenosine triphosphate + L-Glutamic acid + L-Glutamate > Phosphate + Adenosine diphosphate + Hydrogen ion + gamma-Glutamyl-L-putrescine + ADP PW_R002685 gamma-Glutamyl-L-putrescine + Oxygen + Water > 4-(γ-glutamylamino)butanal + Ammonium + Hydrogen peroxide PW_R002686 gamma-Glutamyl-L-putrescine + Oxygen + Hydrogen ion > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + Ammonium PW_R005998 gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxide