S-lactoylglutathione
glycine, N-[S-(2-hydroxy-1-oxopropyl)-N-L-gamma-glutamyl]-L-cysteinyl-
 
Notes:
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). [HMDB]
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CAS Number: 54398-03-7Picture of molecule3D/inchi
FDA UNII: JLC76XF39H
MDL: MFCD06858227
XlogP3-AA: -4.50 (est)
Molecular Weight: 377.37403000
Formula: C13 H19 N3 O8 S
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin conditioning
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
Sigma-Aldrich: Sigma
For experimental / research use only.
S-Lactoylglutathione ≥90% (TLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: cosmetic ingredient for skin conditioning
Recommendation for S-lactoylglutathione usage levels up to:
 not for fragrance use.
 
Recommendation for S-lactoylglutathione flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 20841753
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(2-oxopropanoylsulfanyl)propan-2-yl]amino]-5-oxopentanoic acid
Chemidplus: 0054398037
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References:
 (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(2-oxopropanoylsulfanyl)propan-2-yl]amino]-5-oxopentanoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 20841753
Pubchem (sid): 135250671
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C03451
HMDB (The Human Metabolome Database): HMDB01066
FooDB: FDB022405
YMDB (Yeast Metabolome Database): YMDB00246
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(2-oxopropanoylsulfanyl)propan-2-yl]amino]-5-oxopentanoic acid
 glycine, N-[S-(2-hydroxy-1-oxopropyl)-N-L-gamma-glutamyl]-L-cysteinyl-
S-lactoyl glutathione
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Articles:
PubMed: Promiscuous metallo-β-lactamases: MIM-1 and MIM-2 may play an essential role in quorum sensing networks.
PubMed: Defence against methylglyoxal in Group A Streptococcus: a role for Glyoxylase I in bacterial virulence and survival in neutrophils?
PubMed: Deciphering the role of the type II glyoxalase isoenzyme YcbL (GlxII-2) in Escherichia coli.
PubMed: Lactoylglutathione lyase, a critical enzyme in methylglyoxal detoxification, contributes to survival of Salmonella in the nutrient rich environment.
PubMed: A glutathione responsive rice glyoxalase II, OsGLYII-2, functions in salinity adaptation by maintaining better photosynthesis efficiency and anti-oxidant pool.
PubMed: Understanding the structural requirements for activators of the Kef bacterial potassium efflux system.
PubMed: A metabolomic analysis of omega-3 fatty acid-mediated attenuation of western diet-induced nonalcoholic steatohepatitis in LDLR-/- mice.
PubMed: S-D-Lactoylglutathione can be an alternative supply of mitochondrial glutathione.
PubMed: The roles of sphingosine kinases 1 and 2 in regulating the Warburg effect in prostate cancer cells.
PubMed: A quick, convenient and economical method for the reliable determination of methylglyoxal in millimolar concentrations: the N-acetyl-L-cysteine assay.
PubMed: Optimization of time-course experiments for kinetic model discrimination.
PubMed: S-D-lactoylglutathione as a potential state marker for hemolysis.
PubMed: The critical role of S-lactoylglutathione formation during methylglyoxal detoxification in Escherichia coli.
PubMed: Converting GLX2-1 into an active glyoxalase II.
PubMed: Metabolic engineering of glyoxalase pathway for enhancing stress tolerance in plants.
PubMed: Characterization of the glyoxalase I gene from the vascular wilt fungus Verticillium dahliae.
PubMed: Determination of rat blood S-D-lactoylglutathione by a column-switching high-performance liquid chromatography with precolumn fluorescence derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiazole.
PubMed: The binding of iron and zinc to glyoxalase II occurs exclusively as di-metal centers and is unique within the metallo-beta-lactamase family.
PubMed: Glyoxalase II of African trypanosomes is trypanothione-dependent.
PubMed: In situ kinetic analysis of glyoxalase I and glyoxalase II in Saccharomyces cerevisiae.
PubMed: An XAS investigation of product and inhibitor complexes of Ni-containing GlxI from Escherichia coli: mechanistic implications.
PubMed: A 33-kDa allergen from rice (Oryza sativa L. Japonica). cDNA cloning, expression, and identification as a novel glyoxalase I.
PubMed: Production of S-lactoylglutathione by high activity whole cell biocatalysts prepared by permeabilization of recombinant saccharomyces cerevisiae with alcohols
PubMed: Glyoxalase I from Brassica juncea is a calmodulin stimulated protein.
PubMed: Glyoxalase II in Saccharomyces cerevisiae: in situ kinetics using the 5,5'-dithiobis(2-nitrobenzoic acid) assay.
PubMed: Biochemical and immunochemical characterization of Brassica juncea glyoxalase I.
PubMed: The role of glyoxalase I in the detoxification of methylglyoxal and in the activation of the KefB K+ efflux system in Escherichia coli.
PubMed: Crystal structure of herbicide-detoxifying maize glutathione S-transferase-I in complex with lactoylglutathione: evidence for an induced-fit mechanism.
PubMed: Inhibition of human leukaemia 60 cell growth by S-D-lactoylglutathione in vitro. Mediation by metabolism to N-D-lactoylcysteine and induction of apoptosis.
PubMed: 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.
PubMed: Methylglyoxal and regulation of its metabolism in microorganisms.
PubMed: Prevention of S-D-lactoylglutathione-induced inhibition of human leukaemia 60 cell growth by uridine.
PubMed: Glyoxalase system in clinical diabetes mellitus and correlation with diabetic complications.
PubMed: Thrombin induces S-D-lactoylglutathione accumulation by enhancing platelet glycolytic pathway.
PubMed: S-D-lactoylglutathione accumulation in activated human platelets.
PubMed: Human glyoxalase I. cDNA cloning, expression, and sequence similarity to glyoxalase I from Pseudomonas putida.
PubMed: The assay of S-D-lactoylglutathione in biological systems.
PubMed: Glyoxalase I in micro-organisms: molecular characteristics, genetics and biochemical regulation.
PubMed: The hydrolysis of S-D-lactoylglutathione.
PubMed: Mechanism of the inhibition of growth of human leukaemia 60 cells by S-D-lactoylglutathione.
PubMed: Inhibition of growth of human leukaemia 60 cells by S-2-hydroxyacylglutathione derivatives.
PubMed: The assay of S-D-lactoylglutathione in biological systems.
PubMed: The effect of S-D-lactoylglutathione on the movement of neutrophils.
PubMed: The potentiation of GTP-dependent assembly of microtubules by S-D-lactoylglutathione.
PubMed: Characteristics of the inhibition of human promyelocytic leukaemia HL60 cell growth by S-D-lactoylglutathione in vitro.
PubMed: Physiological and biochemical characterization of glyoxalase I, a general marker for cell proliferation, from a soybean cell suspension.
PubMed: Inhibition of growth of human leukaemia 60 cells by S-2-hydroxyacylglutathiones and monoethyl ester derivatives.
PubMed: Accumulation of S-D-lactoylglutathione and transient decrease of glutathione level caused by methylglyoxal load in isolated hepatocytes.
PubMed: Glyoxalase 2 deficiency in the erythrocytes of a horse: 1H NMR studies of enzyme kinetics and transport of S-lactoylglutathione.
PubMed: The glyoxalase system: new developments towards functional characterization of a metabolic pathway fundamental to biological life.
PubMed: Erythrocyte glyoxalase activity in genetically obese (ob/ob) and streptozotocin diabetic mice.
PubMed: Modification of the glyoxalase system in human red blood cells by glucose in vitro.
PubMed: Modification of the glyoxalase system in human HL60 promyelocytic leukaemia cells during differentiation to neutrophils in vitro.
PubMed: [Glyoxalase I and its application to production of S-lactoylglutathione].
PubMed: Inhibition of proliferation of human promyelocytic leukaemia HL60 cells by S-D-lactoylglutathione in vitro.
PubMed: Metabolism of 2-ketoaldehydes in mold: purification and characterization of glyoxalase I from Aspergillus niger.
PubMed: Purification and active site modification studies on glyoxalase I from monkey intestinal mucosa.
PubMed: S-D-lactoylglutathione in resting and activated human neutrophils.
PubMed: Inhibition of mammalian glyoxalase I (lactoylglutathione lyase) by N-acylated S-blocked glutathione derivatives as a probe for the role of the N-site of glutathione in glyoxalase I mechanism.
PubMed: Platelet glyoxalases in thrombocytosis.
PubMed: 13C NMR studies of the product complex of glyoxalase I.
PubMed: The glutathione-dependent glyoxalase pathway in the yeast Saccharomyces cerevisiae.
PubMed: Involvement of arginine residues in glutathione binding to yeast glyoxalase I.
PubMed: Fluorescence and nuclear relaxation enhancement studies of the binding of glutathione derivatives to manganese-reconstituted glyoxalase I from human erythrocytes. A model for the catalytic mechanism of the enzyme involving a hydrated metal ion.
PubMed: 13-Hydroperoxylinoleic acid inhibits rat liver glyoxalase II.
PubMed: S-2-hydroxyacylglutathione hydrolase (glyoxalase II): active-site mapping of a nonserine thiolesterase.
PubMed: Glutathione thiol esterases of human red blood cells. Fractionation by gel electrophoresis and isoelectric focusing.
PubMed: Effects of S-lactoylglutathione and inhibitors of glyoxalase I on histamine release from human leukocytes.
PubMed: Separation of the isoenzymes of glyoxalase I from human red blood cells by electrophoresis and isoelectric focusing on polyacrylamide gel and by ion exchange chromatography.
PubMed: Concanavalin A increases glyoxalase enzyme activities in polymorphonuclear leukocytes and lymphocytes.
PubMed: gamma,delta-Dioxovalerate as a substrate for the glyoxalase enzyme system.
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