Glutathione disulfide

Glutathione disulfide
Names
	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
CAS Number	27025-41-8;
3D model (JSmol)	Interactive image;
Abbreviations	GSSG
ECHA InfoCard	100.043.777
PubChem CID	65359;
CompTox Dashboard (EPA)	DTXSID5048972 ;
	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
Chemical formula	C20H32N6O12S2
Molar mass	612.631 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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 disulphide through thiol-disulphide exchange with protein disulphide bonds or other low molecular mass compounds, such as Coenzyme A disulphide or dehydroascorbic acid.^[4]

2 GSH + R-S-S-R → GSSG + 2 RSH

References

^ Meister A, Anderson M (1983). "Glutathione". Annu Rev Biochem. 52: 711–60. doi:10.1146/annurev.bi.52.070183.003431. PMID 6137189.
^ Deneke SM, Fanburg BL (1989). "Regulation of cellular glutathione". Am. J. Physiol. 257 (4 Pt 1): L163–73. PMID 2572174. {{cite journal}}: Unknown parameter |month= ignored (help)
^ Meister A (1988). "Glutathione metabolism and its selective modification" (PDF). J Biol Chem. 263 (33): 17205–8. doi:10.1073/pnas.0508621102. PMID 3053703.
^ Holmgren A, Johansson C, Berndt C, Lönn ME, Hudemann C, Lillig CH (2005). "Thiol redox control via thioredoxin and glutaredoxin systems". Biochem. Soc. Trans. 33 (Pt 6): 1375–7. doi:10.1042/BST20051375. PMID 16246122. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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