2.02012-07-30 14:55:21 -06002015-06-03 17:21:11 -0600ECMDB21337M2MDB001737gamma-Glutamyl-gamma-butyraldehydeGamma-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)γ-glutamyl-γ-aminobutyraldehydeg-Glutamyl-g-aminobutyraldehydeg-Glutamyl-g-butyraldehydeGamma-Glutamyl-gamma-aminobutyraldehydeGamma-glutamyl-gamma-butyraldehydeγ-Glutamyl-γ-aminobutyraldehydeγ-Glutamyl-γ-butyraldehydeC9H16N2O4216.2343216.111007012-amino-5-oxo-7-[(2-oxoethyl)amino]heptanoic acid2-amino-5-oxo-7-[(2-oxoethyl)amino]heptanoic acidNC(CCC(=O)CCNCC=O)C(O)=OInChI=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-NCytosollogp-2.41logs-1.33solubility1.00e+01 g/llogp-4.1pka_strongest_acidic2.3pka_strongest_basic8.96iupac2-amino-5-oxo-7-[(2-oxoethyl)amino]heptanoic acidaverage_mass216.2343mono_mass216.11100701smilesNC(CCC(=O)CCNCC=O)C(O)=OformulaC9H16N2O4inchiInChI=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)inchikeySSNXXAXHQSXHKM-UHFFFAOYSA-Npolar_surface_area109.49refractivity52.83polarizability21.86rotatable_bond_count9acceptor_count6donor_count3physiological_charge1formal_charge0Putrescine Degradation IISeveral 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)PW002054Metabolicputrescine degradation IIPWY0-1221Specdb::CMs1083507Specdb::NmrOneD252848Specdb::NmrOneD252849Specdb::NmrOneD252850Specdb::NmrOneD252851Specdb::NmrOneD252852Specdb::NmrOneD252853Specdb::NmrOneD252854Specdb::NmrOneD252855Specdb::NmrOneD252856Specdb::NmrOneD252857Specdb::NmrOneD252858Specdb::NmrOneD252859Specdb::NmrOneD252860Specdb::NmrOneD252861Specdb::NmrOneD252862Specdb::NmrOneD252863Specdb::NmrOneD252864Specdb::NmrOneD252865Specdb::NmrOneD252866Specdb::NmrOneD252867Specdb::MsMs26393Specdb::MsMs26394Specdb::MsMs26395Specdb::MsMs32951Specdb::MsMs32952Specdb::MsMs3295345479698C1570061508GAMMA-GLUTAMYL-GAMMA-AMINOBUTYRALDEHKeseler, 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-D590.21097882Gamma-glutamyl-gamma-aminobutyraldehyde dehydrogenaseP23883PUUC_ECOLIpuuChttp://ecmdb.ca/proteins/P23883.xmlGamma-glutamylputrescine oxidoreductaseP37906PUUB_ECOLIpuuBhttp://ecmdb.ca/proteins/P37906.xmlgamma-Glutamyl-gamma-butyraldehyde + Water + NADP <> 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPHR07418gamma-Glutamyl-L-putrescine + Water + Oxygen > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + AmmoniumRXN0-3921gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxideR07415gamma-Glutamyl-gamma-butyraldehyde + NAD + Water <> 4-(Glutamylamino) butanoate + NADH + Hydrogen ionR07417gamma-Glutamyl-gamma-butyraldehyde + NADP + Water <> 4-(Glutamylamino) butanoate + NADPH + Hydrogen ionR07418NAD(P)<sup>+</sup> + gamma-Glutamyl-gamma-butyraldehyde + Water > 4-(Glutamylamino) butanoate + NAD(P)H + Hydrogen ionRXN0-3922gamma-Glutamyl-L-putrescine + Oxygen + Hydrogen ion > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + AmmoniumPW_R005998gamma-Glutamyl-gamma-butyraldehyde + NADP + Water > gamma-glutamyl-gamma-aminobutyrate + NADPH +2 Hydrogen ionPW_R006000gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxidegamma-Glutamyl-gamma-butyraldehyde + Water + NADP <>4 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH