2.0 2012-05-31 14:30:22 -0600 2015-06-03 17:19:25 -0600 ECMDB20155 M2MDB001002 Glutathionylspermidine Glutathionylspermidine 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). Glutathionylspermidine (Gsp) is a metabolite common to Escherichia coli and protozoal parasites of the Trypanosoma family. (PMID 9398217) Glutathionylspermidine is an intermediate formed in the biosynthesis of trypanothione, an essential metabolite in defence against chemical and oxidative stress in the Kinetoplastida. (PMID 18959765) Glutathionylspermidine is formed as end product and the enzyme lacks TryS activity. (PMID 12049631) GSH-spermidine N1-(&gamma;-L-glutamyl-L-cysteinyl-glycyl)-spermidine N1-(g-L-Glutamyl-L-cysteinyl-glycyl)-spermidine N1-(gamma-L-Glutamyl-L-cysteinyl-glycyl)-spermidine N1-(γ-L-Glutamyl-L-cysteinyl-glycyl)-spermidine C17H34N6O5S 434.554 434.231138918 (2S)-2-amino-4-{[(1R)-1-{[({3-[(4-aminobutyl)amino]propyl}-C-hydroxycarbonimidoyl)methyl]-C-hydroxycarbonimidoyl}-2-sulfanylethyl]-C-hydroxycarbonimidoyl}butanoic acid glutathionylspermidine 33932-35-3 [H][C@](N)(CCC(O)=N[C@@]([H])(CS)C(O)=NCC(O)=NCCCNCCCCN)C(O)=O InChI=1S/C17H34N6O5S/c18-6-1-2-7-20-8-3-9-21-15(25)10-22-16(26)13(11-29)23-14(24)5-4-12(19)17(27)28/h12-13,20,29H,1-11,18-19H2,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t12-,13-/m0/s1 NEDQLXHBVHSKNV-STQMWFEESA-N Cytosol logp -1.59 ALOGPS logs -3.63 ALOGPS solubility 1.01e-01 g/l ALOGPS logp -8.3 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 10.89 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-{[({3-[(4-aminobutyl)amino]propyl}-C-hydroxycarbonimidoyl)methyl]-C-hydroxycarbonimidoyl}-2-sulfanylethyl]-C-hydroxycarbonimidoyl}butanoic acid ChemAxon average_mass 434.554 ChemAxon mono_mass 434.231138918 ChemAxon smiles [H][C@](N)(CCC(O)=N[C@@]([H])(CS)C(O)=NCC(O)=NCCCNCCCCN)C(O)=O ChemAxon formula C17H34N6O5S ChemAxon inchi InChI=1S/C17H34N6O5S/c18-6-1-2-7-20-8-3-9-21-15(25)10-22-16(26)13(11-29)23-14(24)5-4-12(19)17(27)28/h12-13,20,29H,1-11,18-19H2,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t12-,13-/m0/s1 ChemAxon inchikey NEDQLXHBVHSKNV-STQMWFEESA-N ChemAxon polar_surface_area 199.14 ChemAxon refractivity 112.45 ChemAxon polarizability 47.62 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 3 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW000833 ec00480 Metabolic Metabolic pathways eco01100 Specdb::CMs 1083364 Specdb::NmrOneD 301685 Specdb::NmrOneD 301686 Specdb::NmrOneD 301687 Specdb::NmrOneD 301688 Specdb::NmrOneD 301689 Specdb::NmrOneD 301690 Specdb::NmrOneD 301691 Specdb::NmrOneD 301692 Specdb::NmrOneD 301693 Specdb::NmrOneD 301694 Specdb::NmrOneD 301695 Specdb::NmrOneD 301696 Specdb::NmrOneD 301697 Specdb::NmrOneD 301698 Specdb::NmrOneD 301699 Specdb::NmrOneD 301700 Specdb::NmrOneD 301701 Specdb::NmrOneD 301702 Specdb::NmrOneD 301703 Specdb::NmrOneD 301704 Specdb::MsMs 25853 Specdb::MsMs 25854 Specdb::MsMs 25855 Specdb::MsMs 32411 Specdb::MsMs 32412 Specdb::MsMs 32413 440772 142094 C05730 16613 GLUTATHIONYLSPERMIDINE TS5 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 van 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. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Lin, C. H., Kwon, D. S., Bollinger, J. M. Jr, Walsh, C. T. (1997). "Evidence for a glutathionyl-enzyme intermediate in the amidase activity of the bifunctional glutathionylspermidine synthetase/amidase from Escherichia coli." Biochemistry 36:14930-14938. 9398217 Oza, S. L., Ariyanayagam, M. R., Fairlamb, A. H. (2002). "Characterization of recombinant glutathionylspermidine synthetase/amidase from Crithidia fasciculata." Biochem J 364:679-686. 12049631 Oza, S. L., Chen, S., Wyllie, S., Coward, J. K., Fairlamb, A. H. (2008). "ATP-dependent ligases in trypanothione biosynthesis--kinetics of catalysis and inhibition by phosphinic acid pseudopeptides." FEBS J 275:5408-5421. 18959765 Bifunctional glutathionylspermidine synthetase/amidase P0AES0 GSP_ECOLI gsp http://ecmdb.ca/proteins/P0AES0.xml Adenosine triphosphate + Glutathione + Spermidine <> ADP + Glutathionylspermidine + Hydrogen ion + Phosphate R01917 GSPSYN-RXN Glutathionylspermidine + Water <> Glutathione + Spermidine R01918 GSPAMID-RXN Adenosine triphosphate + Glutathione + Spermidine <> ADP + Phosphate + Glutathionylspermidine R01917 Glutathionylspermidine + Water > Glutathione + Spermidine GSPAMID-RXN Spermidine + Glutathione + Adenosine triphosphate > Hydrogen ion + Glutathionylspermidine + ADP + Phosphate GSPSYN-RXN Glutathione + Spermidine + Adenosine triphosphate > Glutathionylspermidine + ADP + Inorganic phosphate