S-Hexylglutathione features a glutathione core extended with a hexyl chain, allowing exploration of hydrophobic-polar transitions. The modified thiol functionality supports binding studies and redox-related interactions. Researchers evaluate its conformational behavior across environments. Use spans detoxification-model research, structural chemistry, and bioconjugation studies.
CAT No: R2679
CAS No:24425-56-7
Synonyms/Alias:s-hexylglutathione;Hexylglutathione;24425-56-7;S-Hexyl-glutathione;S-Hexyl-L-glutathione;NSC 131114;M73SNN908F;CHEBI:27704;L-gamma-glutamyl-S-hexyl-L-cysteinylglycine;CHEMBL345292;Glycine, N-(N-L-gamma-glutamyl-S-hexyl-L-cysteinyl)-;NSC-131114;(2S)-2-azanyl-5-[[(2R)-3-hexylsulfanyl-1-(2-hydroxy-2-oxoethylamino)-1-oxidanylidene-propan-2-yl]amino]-5-oxidanylidene-pentanoic acid;UNII-M73SNN908F;1ydk;(2S)-2-azanyl-5-(((2R)-3-hexylsulfanyl-1-(2-hydroxy-2-oxoethylamino)-1-oxidanylidene-propan-2-yl)amino)-5-oxidanylidene-pentanoic acid;GTX;MFCD00056735;SCHEMBL1158164;2c80;HXJDWCWJDCOHDG-RYUDHWBXSA-N;BDBM50095998;AKOS015893910;CS-W014470;DB04132;HY-W013754;(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-hexylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;NS00069540;C02886;Glycine, L-.gamma.-glutamyl-S-hexyl-L-cysteinyl-;S-Hexyl-L-glutathione (H-L-gGlu-Cys(hexyl)-Gly-OH);(2S)-2-amino-5-[[(1R)-2-(carboxymethylamino)-1-[(hexylthio)methyl]-2-keto-ethyl]amino]-5-keto-valeric acid;(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-(hexylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid;LEE;
S-Hexylglutathione is a specialized biochemical compound belonging to the glutathione derivative family, characterized by the covalent attachment of a hexyl group to the sulfur atom of the cysteine residue within the tripeptide structure. As an S-alkylated glutathione analog, it exhibits unique physicochemical properties that distinguish it from reduced glutathione and related peptides. Its amphiphilic nature and altered redox characteristics make it a valuable tool in biochemical research, particularly for studies involving glutathione-dependent processes, phase II detoxification mechanisms, and protein thiol chemistry. The compound's structural modification enables researchers to investigate the consequences of S-alkylation on glutathione's biological roles and to develop model systems for understanding conjugation reactions relevant to cellular metabolism and xenobiotic transformation.
Enzyme substrate studies: S-Hexylglutathione is widely utilized as a model substrate for glutathione S-transferases (GSTs), a prominent family of phase II detoxification enzymes. The hexyl moiety provides a hydrophobic handle that enhances the compound's interaction with GST isoforms, enabling detailed kinetic analyses and substrate specificity profiling. By employing this derivative, researchers can dissect the mechanistic aspects of GST-catalyzed conjugation reactions, screen for isoform-selective inhibitors, and evaluate the impact of structural modifications on enzyme activity. These studies contribute to a deeper understanding of cellular detoxification pathways and the molecular basis of resistance to electrophilic toxicants.
Affinity chromatography: The unique structure of S-Hexylglutathione allows it to serve as a functional ligand in affinity purification protocols, particularly for the isolation of glutathione-binding proteins. When immobilized on chromatography matrices, it selectively captures GSTs and related thiol-reactive enzymes from complex biological samples. This application is instrumental in proteomics workflows, facilitating the enrichment and characterization of glutathione-interacting proteins, mapping of protein-protein interactions, and elucidation of cellular stress response networks. The approach provides a robust platform for downstream biochemical and structural analyses.
Redox biology research: The S-alkylated form of glutathione offers a valuable probe for investigating thiol-dependent redox processes in cellular systems. Its resistance to standard glutathione reductase-mediated recycling and altered redox potential make it suitable for dissecting noncanonical redox pathways and studying the effects of persistent S-alkylation on cellular homeostasis. Researchers employ S-Hexylglutathione to model the consequences of irreversible thiol modification, thereby gaining insights into oxidative stress mechanisms, protein S-alkylation events, and the regulation of redox-sensitive signaling cascades.
Analytical assay development: The distinctive chemical properties of S-Hexylglutathione support its use in the development and validation of sensitive analytical assays for glutathione-related metabolites and conjugates. It serves as a reference standard or calibration compound in chromatographic and spectrophotometric methods designed to quantify S-alkylated glutathione species in biological samples. These assays enable accurate monitoring of detoxification products, assessment of xenobiotic biotransformation, and evaluation of cellular responses to chemical exposures, thereby advancing research in toxicology, pharmacology, and environmental biochemistry.
Chemical biology tool: As a structurally defined glutathione analog, S-Hexylglutathione is employed as a chemical probe to explore the functional consequences of S-alkylation in peptides and proteins. Its application extends to the design of model conjugates for mechanistic studies, synthesis of labeled derivatives for imaging or detection, and investigation of the structural determinants governing glutathione recognition by enzymes and transporters. The compound's versatility supports a wide range of experimental designs aimed at elucidating the molecular underpinnings of glutathione-dependent processes and the broader landscape of cellular defense mechanisms against electrophilic stress.
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