2.0 2012-07-30 14:55:21 -0600 2015-06-03 17:21:11 -0600 ECMDB21337 M2MDB001737 gamma-Glutamyl-gamma-butyraldehyde Gamma-glutamyl-gamma-butyraldehyde is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Gamma-glutamyl-gamma-butyraldehyde is invovled in Arginine and proline metabolism. (KEGG) &gamma;-glutamyl-&gamma;-aminobutyraldehyde g-Glutamyl-g-aminobutyraldehyde g-Glutamyl-g-butyraldehyde Gamma-Glutamyl-gamma-aminobutyraldehyde Gamma-glutamyl-gamma-butyraldehyde γ-Glutamyl-γ-aminobutyraldehyde γ-Glutamyl-γ-butyraldehyde C9H16N2O4 216.2343 216.11100701 2-amino-5-oxo-7-[(2-oxoethyl)amino]heptanoic acid 2-amino-5-oxo-7-[(2-oxoethyl)amino]heptanoic acid NC(CCC(=O)CCNCC=O)C(O)=O InChI=1S/C9H16N2O4/c10-8(9(14)15)2-1-7(13)3-4-11-5-6-12/h6,8,11H,1-5,10H2,(H,14,15) SSNXXAXHQSXHKM-UHFFFAOYSA-N Cytosol logp -2.41 ALOGPS logs -1.33 ALOGPS solubility 1.00e+01 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 2.3 ChemAxon pka_strongest_basic 8.96 ChemAxon iupac 2-amino-5-oxo-7-[(2-oxoethyl)amino]heptanoic acid ChemAxon average_mass 216.2343 ChemAxon mono_mass 216.11100701 ChemAxon smiles NC(CCC(=O)CCNCC=O)C(O)=O ChemAxon formula C9H16N2O4 ChemAxon inchi InChI=1S/C9H16N2O4/c10-8(9(14)15)2-1-7(13)3-4-11-5-6-12/h6,8,11H,1-5,10H2,(H,14,15) ChemAxon inchikey SSNXXAXHQSXHKM-UHFFFAOYSA-N ChemAxon polar_surface_area 109.49 ChemAxon refractivity 52.83 ChemAxon polarizability 21.86 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon 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 1083507 Specdb::NmrOneD 252848 Specdb::NmrOneD 252849 Specdb::NmrOneD 252850 Specdb::NmrOneD 252851 Specdb::NmrOneD 252852 Specdb::NmrOneD 252853 Specdb::NmrOneD 252854 Specdb::NmrOneD 252855 Specdb::NmrOneD 252856 Specdb::NmrOneD 252857 Specdb::NmrOneD 252858 Specdb::NmrOneD 252859 Specdb::NmrOneD 252860 Specdb::NmrOneD 252861 Specdb::NmrOneD 252862 Specdb::NmrOneD 252863 Specdb::NmrOneD 252864 Specdb::NmrOneD 252865 Specdb::NmrOneD 252866 Specdb::NmrOneD 252867 Specdb::MsMs 26393 Specdb::MsMs 26394 Specdb::MsMs 26395 Specdb::MsMs 32951 Specdb::MsMs 32952 Specdb::MsMs 32953 45479698 C15700 61508 GAMMA-GLUTAMYL-GAMMA-AMINOBUTYRALDEH 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 Gamma-glutamyl-gamma-aminobutyraldehyde dehydrogenase P23883 PUUC_ECOLI puuC http://ecmdb.ca/proteins/P23883.xml Gamma-glutamylputrescine oxidoreductase P37906 PUUB_ECOLI puuB http://ecmdb.ca/proteins/P37906.xml gamma-Glutamyl-gamma-butyraldehyde + Water + NADP <> 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH R07418 gamma-Glutamyl-L-putrescine + Water + Oxygen > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + Ammonium RXN0-3921 gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxide R07415 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 gamma-Glutamyl-L-putrescine + Oxygen + Hydrogen ion > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + Ammonium PW_R005998 gamma-Glutamyl-gamma-butyraldehyde + NADP + Water > gamma-glutamyl-gamma-aminobutyrate + NADPH +2 Hydrogen ion PW_R006000 gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxide gamma-Glutamyl-gamma-butyraldehyde + Water + NADP <>4 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH