S-Methylglutathione assumes a vital role in shielding cells against the detrimental effects of oxidative stress, consequently serving as an efficacious therapeutic agent for numerous ailments including hepatic dysfunctions, neurodegenerative pathologies, and malignant conditions. Moreover, S-Methylglutathione offers comprehensive health benefits while concurrently reinforcing cellular structure and function.
CAT No: R2063
CAS No:2922-56-7
Synonyms/Alias:S-Methylglutathione;S-Methyl glutathione;2922-56-7;Glutathione ester;S-METHYL-GLUTATHIONE;Glutathione S-methyl ester;S-Methyl GSH;L-gamma-Glutamyl-S-methyl-L-cysteinylglycine;Glycine, L-gamma-glutamyl-S-methyl-L-cysteinyl-;OOW3025SR1;S-METHYL-GSH;CHEBI:141472;DTXSID10183479;L-GAMMA-GLUTAMYL-S-METHYLCYSTEINYLGLYCINE;Glycine, N-(N-L-gamma-glutamyl-S-methyl-L-cysteinyl)-;(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-methylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;GLYCINE, L-.GAMMA.-GLUTAMYL-S-METHYL-L-CYSTEINYL-;N5-((R)-1-((carboxymethyl)amino)-3-(methylthio)-1-oxopropan-2-yl)-L-glutamine;(2S)-2-amino-5-[[(1R)-2-(carboxymethylamino)-1-(methylsulfanylmethyl)-2-oxo-ethyl]amino]-5-oxo-pentanoic acid;GSM;UNII-OOW3025SR1;gamma-L-glutamyl-(S-methyl)-L-cysteinyl-glycine;(2S)-2-amino-5-(((1R)-2-(carboxymethylamino)-1-(methylsulfanylmethyl)-2-oxo-ethyl)amino)-5-oxo-pentanoic acid;glutathione, S-methyl-;SCHEMBL1767370;CHEMBL1233129;DTXCID70105970;QTQDDTSVRVWHMO-BQBZGAKWSA-N;BDBM225232;AKOS040746355;CS-W009893;DB04701;FM45828;HY-W009177;1ST40004;AS-77779;DA-67641;NS00068559;Glycine, L-?-glutamyl-S-methyl-L-cysteinyl-;D95549;SR-01000884011;SR-01000884011-1;Q27095444;(S)-2-Amino-5-(((R)-1-((carboxymethyl)amino)-3-(methylthio)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid;(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-(methylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid;
Chemical Name:(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-methylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
S-Methylglutathione is a specialized glutathione derivative in which the sulfhydryl group of the cysteine residue has been methylated, resulting in a thioether moiety. As a tripeptide analog structurally related to reduced glutathione (GSH), it retains the core γ-glutamyl-cysteinyl-glycine backbone but exhibits altered redox and nucleophilic properties. This compound is of significant interest in biochemical research due to its unique reactivity profile, its role as a model compound for methylation-related metabolic pathways, and its utility in elucidating mechanisms of thiol-mediated cellular processes. The methylation of the thiol group imparts distinct physicochemical characteristics, making S-Methylglutathione an important tool for probing glutathione-dependent enzymatic reactions, oxidative stress responses, and sulfur biochemistry.
Enzyme substrate specificity studies: S-Methylglutathione serves as a valuable probe for investigating the substrate selectivity of glutathione-dependent enzymes such as glutathione S-transferases (GSTs) and glutaredoxins. By substituting the reactive thiol with a methylthio group, researchers can assess how methylation affects enzyme recognition, catalytic activity, and binding affinity. This enables detailed mapping of active site preferences and provides insights into the structural requirements for glutathione conjugation and redox regulation, contributing to the broader understanding of detoxification pathways and cellular antioxidant defense mechanisms.
Redox biology research: The methylated thiol group in this compound renders it incapable of participating in typical thiol-disulfide exchange reactions, distinguishing it from native GSH. Utilizing S-Methylglutathione in redox biology experiments allows scientists to dissect the specific contributions of the glutathione thiol to cellular redox homeostasis. By comparing its behavior to that of reduced and oxidized glutathione, researchers can clarify the roles of free thiols in buffering oxidative stress, modulating redox-sensitive signaling, and maintaining protein thiol status in biological systems.
Metabolism and methylation pathway analysis: As a model substrate, S-Methylglutathione is instrumental in studying S-methylation reactions and the fate of methylated sulfur compounds in metabolic networks. Its use facilitates the investigation of enzymatic and non-enzymatic methylation processes, the turnover of methylated glutathione species, and the transport and catabolism of sulfur-containing metabolites. These studies are particularly relevant for elucidating the biochemical consequences of altered methylation capacity, methionine cycle flux, and related metabolic disorders.
Analytical method development: The unique structural features of S-Methylglutathione make it a suitable standard or reference compound for the development and validation of analytical techniques targeting glutathione derivatives. Its distinct chromatographic and mass spectrometric signatures enable precise calibration and quantification in complex biological matrices. Researchers employ it to optimize detection methods for glutathione conjugates, assess the specificity of derivatization protocols, and improve the accuracy of redox metabolite profiling in cellular extracts or tissue samples.
Chemical biology and thiol reactivity studies: The presence of a methylthio moiety instead of a free thiol provides a strategic advantage for chemical biology applications aimed at dissecting thiol-mediated processes. S-Methylglutathione is utilized to evaluate the reactivity and selectivity of thiol-targeting reagents, inhibitors, or labeling agents in the absence of a nucleophilic sulfhydryl group. This enables the differentiation between thiol-dependent and thiol-independent mechanisms in protein modification, small molecule interactions, and cellular signaling pathways, thereby advancing the understanding of sulfur chemistry in biological systems.
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