2.0 2012-05-31 13:44:25 -0600 2015-06-03 15:53:41 -0600 ECMDB01066 M2MDB000239 S-Lactoylglutathione S-Lactoylglutathione is a substrate of lactoylglutathione lyase [EC 4.4.1.5] in pyruvate metabolism (KEGG). Another enzyme, glyoxalase I, synthesizes this compound by converting methylglyoxal and reduced glutathione to S-lactoylglutathione. S-D-lactoylglutathione can be hydrolysed by thiolesterases to reduced glutathione and D-lactate but also converted to N-D-lactoylcysteinylglycine and N-D-lactoylcysteine by gamma-glutamyl transferase and dipeptidase (PMID: 8632674). S-lactoylglutathione has also been shown to modulate microtubule assembly (PMID: 690442). (R)-S-lactoylglutathione D-Lactoylglutathione Delta-Lactoylglutathione N-(N-L-g-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine N-(N-L-gamma-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine N-(N-L-γ-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine S-D-Lactoyl-glutathione S-D-Lactoylglutathione S-delta-Lactoyl-glutathione S-delta-Lactoylglutathione S-Lactate glutathione S-Lactateglutathione S-Lactic acid glutathione S-Lactoyl-glutathione S-Lactylglutathione S-[(2R)-2-Hydroxypropanoyl]-g-L-glutamyl-L-cysteinylglycine S-[(2R)-2-Hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine S-[(2R)-2-Hydroxypropanoyl]-γ-L-glutamyl-L-cysteinylglycine S-δ-Lactoyl-glutathione S-δ-Lactoylglutathione SL-GSH δ-Lactoylglutathione C13H21N3O8S 379.386 379.104935353 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid S-lactoylglutathione 25138-66-3 C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1 VDYDCVUWILIYQF-CSMHCCOUSA-N Solid Cytosol logp -2.88 ALOGPS logs -1.70 ALOGPS solubility 7.55e+00 g/l ALOGPS logp -5.4 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid ChemAxon average_mass 379.386 ChemAxon mono_mass 379.104935353 ChemAxon smiles C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O ChemAxon formula C13H21N3O8S ChemAxon inchi InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1 ChemAxon inchikey VDYDCVUWILIYQF-CSMHCCOUSA-N ChemAxon polar_surface_area 196.12 ChemAxon refractivity 84.78 ChemAxon polarizability 36.01 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pyruvate metabolism ec00620 methylglyoxal degradation I PWY-5386 Specdb::CMs 2679 Specdb::CMs 37913 Specdb::CMs 175347 Specdb::NmrOneD 146230 Specdb::NmrOneD 146231 Specdb::NmrOneD 146232 Specdb::NmrOneD 146233 Specdb::NmrOneD 146234 Specdb::NmrOneD 146235 Specdb::NmrOneD 146236 Specdb::NmrOneD 146237 Specdb::NmrOneD 146238 Specdb::NmrOneD 146239 Specdb::NmrOneD 146240 Specdb::NmrOneD 146241 Specdb::NmrOneD 146242 Specdb::NmrOneD 146243 Specdb::NmrOneD 146244 Specdb::NmrOneD 146245 Specdb::NmrOneD 146246 Specdb::NmrOneD 146247 Specdb::NmrOneD 146248 Specdb::NmrOneD 146249 Specdb::MsMs 27680 Specdb::MsMs 27681 Specdb::MsMs 27682 Specdb::MsMs 34238 Specdb::MsMs 34239 Specdb::MsMs 34240 Specdb::MsMs 438036 Specdb::MsMs 438037 Specdb::MsMs 438038 Specdb::MsMs 438039 Specdb::MsMs 438040 Specdb::MsMs 439186 Specdb::MsMs 446430 Specdb::MsMs 446431 Specdb::MsMs 446432 Specdb::MsMs 446433 Specdb::MsMs 446434 Specdb::MsMs 447237 Specdb::MsMs 448134 Specdb::MsMs 2832237 Specdb::MsMs 2832238 Specdb::MsMs 2832239 Specdb::MsMs 2850289 Specdb::MsMs 2850290 Specdb::MsMs 2850291 HMDB01066 119450 389032 C03451 15694 S-LACTOYL-GLUTATHIONE 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 Edwards, L. G., Adesida, A., Thornalley, P. J. (1996). "Inhibition of human leukaemia 60 cell growth by S-D-lactoylglutathione in vitro. Mediation by metabolism to N-D-lactoylcysteine and induction of apoptosis." Leuk Res 20:17-26. 8632674 Gillespie, E. (1978). "Concanavalin A increases glyoxalase enzyme activities in polymorphonuclear leukocytes and lymphocytes." J Immunol 121:923-925. 690442 Thornalley PJ: Advances in glyoxalase research. Glyoxalase expression in malignancy, anti-proliferative effects of methylglyoxal, glyoxalase I inhibitor diesters and S-D-lactoylglutathione, and methylglyoxal-modified protein binding and endocytosis by the advanced glycation endproduct receptor. Crit Rev Oncol Hematol. 1995 Aug;20(1-2):99-128. 7576201 Irsch T, Krauth-Siegel RL: Glyoxalase II of African trypanosomes is trypanothione-dependent. J Biol Chem. 2004 May 21;279(21):22209-17. Epub 2004 Feb 19. 14976196 Liu, Yan; Hama, Hideki; Fujita, Yasuya; Kondo, Akihiko; Inoue, Yoshiharu; Kimura, Akira; Fu Production of S-lactoylglutathione by high activity whole cell biocatalysts prepared by permeabilization of recombinant Saccharomyces cerevisiae with alcohols. Lactoylglutathione lyase P0AC81 LGUL_ECOLI gloA http://ecmdb.ca/proteins/P0AC81.xml Hydroxyacylglutathione hydrolase P0AC84 GLO2_ECOLI gloB http://ecmdb.ca/proteins/P0AC84.xml Oligopeptide transport system permease protein oppB P0AFH2 OPPB_ECOLI oppB http://ecmdb.ca/proteins/P0AFH2.xml Oligopeptide transport system permease protein oppC P0AFH6 OPPC_ECOLI oppC http://ecmdb.ca/proteins/P0AFH6.xml Oligopeptide transport system permease protein oppB P0AFH2 OPPB_ECOLI oppB http://ecmdb.ca/proteins/P0AFH2.xml Oligopeptide transport system permease protein oppC P0AFH6 OPPC_ECOLI oppC http://ecmdb.ca/proteins/P0AFH6.xml Water + S-Lactoylglutathione > Glutathione + Hydrogen ion + D-Lactic acid R01736 GLYOXII-RXN Glutathione + Pyruvaldehyde <> S-Lactoylglutathione R02530 GLYOXI-RXN S-Lactoylglutathione + Water <> Glutathione + D-Lactic acid R01736 GLYOXII-RXN S-Lactoylglutathione <> Glutathione + Pyruvaldehyde R02530 GLYOXI-RXN S-Lactoylglutathione < Pyruvaldehyde + Glutathione GLYOXI-RXN S-Lactoylglutathione > Glutathione + Pyruvaldehyde Pyruvaldehyde + Glutathione > S-Lactoylglutathione PW_R006149 S-Lactoylglutathione + Water > Glutathione + Hydrogen ion + L-Lactic acid PW_R006150 Glutathione + Pyruvaldehyde <> S-Lactoylglutathione