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Antioxidant
An endogenous antioxidant tripeptide investigated in cellular redox biology and detoxification enzymology research.
Reviewed by Dr. James Whitfield, PharmD · Published · Last reviewed · For research use only.
Type
Tripeptide (gamma-glutamyl thiol)
Molecular formula
C10H17N3O6S
Molecular weight
307.32 g/mol
CAS number
70-18-8
Amino acids
3
Sequence
gamma-Glu-Cys-Gly
Modification
γ-peptide (isopeptide) bond linking the γ-carboxyl of glutamate to the α-amino group of cysteine; reactive free cysteine thiol (reduced form, GSH).
A γ-glutamyl tripeptide bearing a reactive cysteine thiol; the unusual γ-peptide bond confers resistance to standard aminopeptidase cleavage. The thiol serves as a one- and two-electron reductant, acting as co-substrate for glutathione peroxidases (via a selenenyl-glutathione adduct in the selenol ping-pong mechanism) and for glutathione S-transferases (nucleophilic conjugation of electrophilic substrates). The compound cycles between the reduced monomeric thiol (GSH) and the oxidized disulfide dimer (GSSG); regeneration of GSH from GSSG is catalyzed by glutathione reductase, a FAD-dependent flavoenzyme, linking glutathione availability to the intracellular NADPH pool.
Lyophilized
20°C
store desiccated; air-sensitive.
Air-sensitive (thiol oxidation to GSSG); store under desiccant; avoid prolonged solution storage
Reviews
Bachhawat AK, Yadav S. (2018). IUBMB Life
Forman HJ, Zhang H, Rinna A. (2009). Mol Aspects Med
Lu SC. (2009). Mol Aspects Med
Reviews
Townsend DM, Tew KD. (2003). Oncogene
Sheehan D, Meade G, Foley VM, Dowd CA. (2001). Biochem J
Schafer FQ, Buettner GR. (2001). Free Radic Biol Med
Sies H. (1999). Free Radic Biol Med
Meister A, Anderson ME. (1983). Annu Rev Biochem
Clinical
Kalamkar S, et al. (2022). Antioxidants
Sekhar RV, et al. (2022). Front Aging
ClinicalTrials.gov.. ClinicalTrials.gov
Allen J, Bradley RD.. Altern Med Rev
Primary research
Borchert A, et al. (2018). Biochim Biophys Acta Mol Cell Biol Lipids
Dixon SJ, Lemberg KM, Lamprecht MR, et al. (2012). Cell
Polekhina G, Board PG, Gali RR, Rossjohn J, Parker MW. (1999). EMBO J
Sian J, Dexter DT, Lees AJ, et al. (1994). Ann Neurol
Karplus PA, Schulz GE. (1987). J Mol Biol
Pai EF, Schulz GE. (1983). J Biol Chem
Griffith OW, Meister A. (1979). J Biol Chem
Griffith OW, Anderson ME, Meister A. (1979). J Biol Chem
Tietze F. (1969). Anal Biochem
Also known as: GSH, L-glutathione (reduced), γ-L-glutamyl-L-cysteinylglycine
Research Use Only
These products are intended for research purposes only and are not for human consumption. Not FDA approved. Not intended to diagnose, treat, cure, or prevent any disease.
Quality & methods