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 derivative of glutathione, recognized for its unique molecular structure that incorporates a hexyl group into the tripeptide backbone. This modification enhances its lipophilicity, allowing for improved membrane permeability and distinctive biochemical behaviors compared to its parent compound. As a result, S-Hexylglutathione is frequently utilized in research settings where a more hydrophobic analog of glutathione is advantageous. Its ability to interact with both aqueous and lipid environments makes it a valuable tool for investigating cellular redox states, detoxification pathways, and mechanisms of oxidative stress. Researchers appreciate its stability and versatility, which facilitate a broad range of experimental designs aimed at elucidating the functions of thiol-containing molecules in biological systems.
Redox Biology Research: S-Hexylglutathione serves as an important probe in the study of redox biology, particularly in the context of glutathione-dependent enzymatic reactions. Its increased hydrophobicity allows it to mimic cellular glutathione in environments where membrane association or lipid solubility is critical. Scientists often employ this compound to dissect the roles of glutathione S-transferases and peroxidases, investigating how modified glutathione analogs affect the kinetics and specificity of these enzymes. By observing the interactions of S-Hexylglutathione with various protein targets, researchers gain valuable insights into the modulation of redox-sensitive signaling pathways and the maintenance of cellular redox homeostasis.
Detoxification Mechanisms: In studies focused on detoxification, S-Hexylglutathione is used to model and assess the conjugation of xenobiotics and endogenous toxins. Its structure enables it to participate in glutathione conjugation reactions, serving as a substrate or competitor in assays that evaluate the capacity of cells to neutralize reactive intermediates. This application is particularly relevant in toxicology research, where understanding the fate of lipophilic toxins and their interactions with glutathione analogs can inform the development of protective strategies and interventions. S-Hexylglutathione's behavior in these assays provides a detailed perspective on the mechanisms underlying cellular defense against chemical stressors.
Membrane Transport Studies: The enhanced lipophilicity of S-Hexylglutathione makes it a preferred model for investigating membrane transport processes involving glutathione derivatives. Researchers utilize it to study the uptake, efflux, and compartmentalization of glutathione-based molecules across various biological membranes, including those of mitochondria, endoplasmic reticulum, and the plasma membrane. By tracking its distribution and transport kinetics, scientists can decipher the roles of specific transporters and channels, as well as the impact of structural modifications on glutathione's bioavailability and cellular localization.
Enzyme Inhibition and Substrate Specificity: S-Hexylglutathione is frequently employed to probe the substrate specificity and inhibition profiles of enzymes that recognize glutathione or its analogs. Its unique structure allows for the evaluation of how hydrophobic modifications influence enzyme binding and catalytic activity. This application is essential in enzymology studies aimed at characterizing the selectivity of glutathione-utilizing enzymes, as well as in the screening of potential inhibitors that could modulate these critical biological processes. Such research advances our understanding of enzyme-substrate interactions and supports the design of novel biochemical tools.
Oxidative Stress Modeling: In the context of oxidative stress research, S-Hexylglutathione provides a valuable means to simulate and analyze the cellular responses to increased reactive oxygen species. By incorporating this analog into cell culture or biochemical assays, investigators can observe alterations in antioxidant capacity, glutathione cycling, and the activation of stress-responsive pathways. Its use enables a more nuanced exploration of how lipid-soluble glutathione derivatives contribute to the mitigation of oxidative damage, supporting the development of new strategies for maintaining redox balance in challenging environments.
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