Glutathione disulfide

Glutathione disulfide
IUPAC name (2S)-2-amino-5-[[(2R)-3-[(2R)-2-[[(4S)-4-amino-5-hydroxy-5-oxopentanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl-1- (carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Identifiers
Abbreviations	GSSG
CAS number	27025-41-8 Y
PubChem	65359
Jmol-3D images	Image 1
SMILES C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
Properties
Molecular formula	C20H32N6O12S2
Molar mass	612.631 g/mol
Y disulfide (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glutathione disulfide (GSSG) is a disulfide derived from two glutathione molecules.^[1]

In living cells, glutathione disulfide is reduced into two molecules of glutathione with reducing equivalents from the coenzyme NADPH. This reaction is catalyzed by the enzyme glutathione reductase.^[2] Antioxidant enzymes, such as glutathione peroxidases and peroxiredoxins, generate glutathione disulfide during the reduction of peroxides such as hydrogen peroxide (H₂O₂) and organic hydroperoxides (ROOH):^[3]

2 GSH + ROOH → GSSG + ROH + H₂O

Other enzymes, such as glutaredoxins, generate glutathione disulfide through thiol-disulfide exchange with protein disulfide bonds or other low molecular mass compounds, such as coenzyme A disulfide or dehydroascorbic acid.^[4]

2 GSH + R-S-S-R → GSSG + 2 RSH

See also

• Glutathione-ascorbate cycle
• NOV-002
• NOV-205
• Antioxidants

References

1. ^ Meister A, Anderson M (1983). "Glutathione". Annu Rev Biochem 52: 711–60. doi:10.1146/annurev.bi.52.070183.003431. PMID 6137189. 
2. ^ Deneke SM, Fanburg BL (October 1989). "Regulation of cellular glutathione". Am. J. Physiol. 257 (4 Pt 1): L163–73. PMID 2572174. 
3. ^ Meister A (1988). "Glutathione metabolism and its selective modification" (PDF). J Biol Chem 263 (33): 17205–8. PMID 3053703. http://www.jbc.org/cgi/reprint/263/33/17205.pdf. 
4. ^ Holmgren A, Johansson C, Berndt C, Lönn ME, Hudemann C, Lillig CH (December 2005). "Thiol redox control via thioredoxin and glutaredoxin systems". Biochem. Soc. Trans. 33 (Pt 6): 1375–7. doi:10.1042/BST20051375. PMID 16246122.