Glutathione disulfide

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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
27025-41-8 YesY
Abbreviations GSSG
ChEMBL ChEMBL1372 N
ChemSpider 58835 N
6835
Jmol 3D model Interactive image
PubChem 65359
11215652
  • InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 N
    Key: YPZRWBKMTBYPTK-BJDJZHNGSA-N N
  • InChI=1/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
    Key: YPZRWBKMTBYPTK-BJDJZHNGBD
  • 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
C20H32N6O12S2
Molar mass 612.631 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

Neuromodulator

GSSG, along with glutathione and S-nitrosoglutathione (GSNO), have been found to bind to the glutamate recognition site of the NMDA and AMPA receptors (via their γ-glutamyl moieties), and may be endogenous neuromodulators.[5][6] At millimolar concentrations, they may also modulate the redox state of the NMDA receptor complex.[6]

See also

References

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