Glutathione disulfide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Glutathione disulfide
Glutathione disulfide.svg
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
Abbreviations GSSG
27025-41-8 YesY
ChEMBL ChEMBL1372 N
ChemSpider 58835 N
Jmol-3D images Image
PubChem 65359
11215652
Properties
C20H32N6O12S2
Molar mass 612.631 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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[edit]

References[edit]

  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. 
  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.