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 (Jmol)	Interactive image
Abbreviations	GSSG
ChEMBL	ChEMBL1372
ChemSpider	58835
ECHA InfoCard	100.043.777
IUPHAR/BPS	6835
PubChem	65359 11215652
InChI 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 Key: YPZRWBKMTBYPTK-BJDJZHNGSA-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
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).
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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

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

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.
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.
5. Steullet, P.; Neijt, H.C.; Cuénod, M.; Do, K.Q. (2006). "Synaptic plasticity impairment and hypofunction of NMDA receptors induced by glutathione deficit: Relevance to schizophrenia". Neuroscience. 137 (3): 807–819. doi:10.1016/j.neuroscience.2005.10.014. ISSN 0306-4522.
6. Varga, V.; Jenei, Zs.; Janáky, R.; Saransaari, P.; Oja, S. S. (1997). "Glutathione Is an Endogenous Ligand of Rat Brain N-Methyl-D-Aspartate (NMDA) and 2-Amino-3-Hydroxy-5-Methyl-4-Isoxazolepropionate (AMPA) Receptors". Neurochemical Research. 22 (9): 1165–1171. doi:10.1023/A:1027377605054. ISSN 0364-3190.