Glutathione

An endogenous antioxidant tripeptide investigated in cellular redox biology and detoxification enzymology research.

View Glutathione in the store

Molecular Profile

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).

Mechanism & Target Class

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.

Storage & Handling

Lyophilized
-20°C; store desiccated; air-sensitive.
Handling
Air-sensitive (thiol oxidation to GSSG); store under desiccant; avoid prolonged solution storage; minimize headspace in reconstituted solutions.

Primary Database

PubChem CID 124886 ↗

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