Homoglutathione extends the classical glutathione tripeptide with modified residue composition that influences redox behavior. Its thiol group supports studies of oxidative pathways and disulfide exchange. Researchers explore its structural transitions and metal-binding properties. Uses include biochemical redox modeling, detoxification studies, and thiol-based interaction research.
CAT No: R2482
CAS No:18710-27-5
Synonyms/Alias:homoglutathione;18710-27-5;L-gamma-glutamyl-L-cysteinyl-beta-alanine;(2S)-2-amino-5-[[(2R)-1-(2-carboxyethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid;H-GLU(CYS-BETA-ALA-OH)-OH;L=L-Homoglutathione;MFCD01318801;C04544;SCHEMBL2067187;CHEBI:17078;DTXSID301317148;HY-P4450;gamma-glutamyl-cysteinyl-beta-alanine;Homoglutathione (H-gGlu-Cys-bAla-OH);DA-74257;FH109127;Homoglutathione H-Glu(Cys-b-Ala-OH)-OH;Q27102200;2-amino-4-({1-[(2-carboxyethyl)carbamoyl]-2-sulfanylethyl}carbamoyl)butanoic acid;N5-((R)-1-((2-Carboxyethyl)amino)-3-mercapto-1-oxopropan-2-yl)-L-glutamine;
Homoglutathione is a naturally occurring tripeptide structurally related to glutathione, distinguished by the substitution of β-alanine in place of glycine at the C-terminal position. As a key low-molecular-weight thiol, it is predominantly found in leguminous plants, where it plays vital roles in redox homeostasis and cellular defense mechanisms. Its unique structure and functional properties have attracted significant interest in plant biochemistry, redox biology, and comparative studies of thiol metabolism. Researchers utilize homoglutathione to explore the nuances of thiol-based antioxidant systems, stress responses, and metabolic regulation in both plant and broader biological systems.
Redox biology research: Homoglutathione serves as an important model compound for investigating thiol-based redox regulation in plant systems. Its presence in legumes and its functional similarity to glutathione allow scientists to dissect the specific contributions of different tripeptides to cellular redox buffering, detoxification of reactive oxygen species, and maintenance of redox equilibrium. In experimental setups, homoglutathione enables the study of thiol-disulfide exchange reactions and the elucidation of mechanisms underlying oxidative stress tolerance, providing insights into plant adaptation and defense.
Plant stress physiology: In the context of plant biology, homoglutathione is used to examine the biochemical pathways involved in responses to abiotic and biotic stressors such as drought, salinity, and pathogen attack. Its role as an alternative or complementary antioxidant to glutathione in certain species offers a valuable tool for differentiating the impact of distinct thiol pools in stress mitigation. Researchers employ this tripeptide to track changes in thiol metabolism under stress conditions and to evaluate its influence on the regulation of key enzymes involved in detoxification and repair processes.
Enzymatic substrate studies: The unique β-alanine residue in homoglutathione makes it a valuable substrate for characterizing the specificity and kinetics of plant glutathione synthetases and homoglutathione synthetases. By using the compound in enzyme assays, scientists can analyze substrate preferences, catalytic efficiency, and mechanistic differences between homologous enzymes. These studies contribute to a deeper understanding of the evolution and diversification of thiol metabolism in plants, as well as the regulation of tripeptide synthesis.
Analytical standard in metabolomics: Homoglutathione is frequently employed as a reference standard in chromatographic and mass spectrometric analyses for the identification and quantification of low-molecular-weight thiols in plant extracts. Its use enhances the accuracy of metabolomic profiling, enabling researchers to distinguish between glutathione, homoglutathione, and related compounds. This capability is essential for mapping metabolic fluxes, assessing redox status, and interpreting physiological states in leguminous and non-leguminous species.
Comparative biochemical studies: The structural and functional parallels between homoglutathione and glutathione make the former a critical tool for comparative studies across diverse biological systems. By substituting or supplementing glutathione with homoglutathione in in vitro assays or cell-free systems, researchers can explore the specificity of thiol-dependent enzymes, transporters, and signaling pathways. Such investigations provide valuable information on the evolutionary adaptations of thiol metabolism and its implications for cellular resilience, metabolic regulation, and species-specific physiological traits.
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