Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:44:25 -0600 |
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Update Date | 2015-06-03 15:53:41 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | S-Lactoylglutathione |
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Description | 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). |
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Structure | |
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Synonyms: | - (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
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Chemical Formula: | C13H21N3O8S |
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Weight: | Average: 379.386 Monoisotopic: 379.104935353 |
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InChI Key: | VDYDCVUWILIYQF-CSMHCCOUSA-N |
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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 |
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CAS number: | 25138-66-3 |
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IUPAC Name: | (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid |
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Traditional IUPAC Name: | S-lactoylglutathione |
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SMILES: | C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Oligopeptides |
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Alternative Parents | |
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Substituents | - Alpha-oligopeptide
- Gamma-glutamyl alpha peptide
- S-(2-hydroxyacyl)glutathione
- S-acylglutathione
- Glutamine or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Alpha-amino acid amide
- Cysteine or derivatives
- Alpha-amino acid
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- N-acyl-amine
- Fatty acyl
- Fatty amide
- Dicarboxylic acid or derivatives
- Fatty acid
- Secondary carboxylic acid amide
- Secondary alcohol
- Amino acid or derivatives
- Thiocarboxylic acid ester
- Amino acid
- Carboxamide group
- Carbothioic s-ester
- Sulfenyl compound
- Carboxylic acid
- Thiocarboxylic acid or derivatives
- Organosulfur compound
- Primary amine
- Organic nitrogen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary aliphatic amine
- Organooxygen compound
- Organonitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | |
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-022d-9025000000-e8442b76e42e68182070 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0f8c-6700390000-be9c9075535b7b68d56c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0109000000-a34d20761c4d6bee6ff4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-05dj-0769000000-125dd04c3309557ca71d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-02f1-2930000000-bab00ec3c9a62c353d98 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004l-2900000000-ed3b919674c5534985e4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-005c-9800000000-c037ad2006918e401b23 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-1935000000-5775999bbe10e3b4c9db | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-0019000000-99436ad12d519791de4e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001j-3693000000-a466eff4cff41d7086c7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0032-1930000000-18d451bef69e367a6364 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-003s-8900000000-15e831c7f610fbcdf31c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-003r-9300000000-c6405af72f8eaaf2cb11 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-001i-0290000000-ef71ecf2559bf8a8090d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-9873000000-760e0e4073de1137832e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-1149000000-62e5724126eead68b1cc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-003r-6494000000-e3b7d776638d1bad4552 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fba-3970000000-ead14f990fca59e626ed | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a70-0059000000-93c2a2c66ec470d5e065 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-5398000000-b0a25646cfd9bdbb68e1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9200000000-d10281b62f65d09c7238 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0019000000-738e521a28b7b76a5117 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08ml-0960000000-6303aeec8244b3481bcd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-4910000000-35e994483e5244ab5642 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0019000000-a681d82646af48a3b592 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000t-4965000000-c35d5adc9f5c770c3706 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03gi-1950000000-cb8ea7b94c227704fc5a | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - 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. Pubmed: 8632674
- Gillespie, E. (1978). "Concanavalin A increases glyoxalase enzyme activities in polymorphonuclear leukocytes and lymphocytes." J Immunol 121:923-925. Pubmed: 690442
- 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. Pubmed: 14976196
- 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. Pubmed: 22080510
- 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. Pubmed: 21097882
- 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. Pubmed: 7576201
- 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. Pubmed: 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. Pubmed: 18331064
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Synthesis Reference: | 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. |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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