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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: glutathione disulfide

Abbrev Name: GSSG

Synonyms: glutathione oxidized, glutathione ox, GSSG, oxidized glutathione

Chemical Formula: C20H30N6O12S2

Molecular Weight: 610.61 Daltons

Monoisotopic Molecular Weight: 612.1519619036 Daltons

SMILES: C(SSCC(C(NCC([O-])=O)=O)NC(=O)CCC([N+])C([O-])=O)C(C(NCC([O-])=O)=O)NC(=O)CCC([N+])C([O-])=O

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)/p-2/t9-,10-,11-,12-/m0/s1

InChIKey: InChIKey=YPZRWBKMTBYPTK-BJDJZHNGSA-L

Unification Links: CAS:27025-41-8 , ChEBI:58297 , HMDB:HMDB03337 , IAF1260:33951 , KEGG:C00127 , MetaboLights:MTBLC58297 , PubChem:25245992

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -127.84466 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glutathione redox reactions I , glutathione redox reactions II :
2 glutathione + NADP+glutathione disulfide + NADPH + H+

sulfide oxidation III (sulfur dioxygenase) :
hydrogen sulfide + glutathione disulfide → S-sulfanylglutathione + glutathione

Reactions known to produce the compound:

arsenate detoxification I (glutaredoxin) :
2 glutathione + methylarsonate → glutathione disulfide + methylarsonite

ascorbate glutathione cycle , ascorbate recycling (cytosolic) :
L-dehydro-ascorbate + 2 glutathione → L-ascorbate + glutathione disulfide + H+

drosopterin and aurodrosopterin biosynthesis :
2-amino-6-acetyl-3,7,8,9-tetrahydro-3H-pyrimido[4,5-b][1,4]diazepin-4-one + glutathione disulfide + H2O ← 6-pyruvoyl tetrahydropterin + 2 glutathione

glutathione redox reactions I :
hydrogen peroxide + 2 glutathione → glutathione disulfide + 2 H2O
a lipid hydroperoxide + 2 glutathione + H+ → a lipid + glutathione disulfide + 2 H2O

glutathione redox reactions II :
2 glutathione + an oxidized glutaredoxin → glutathione disulfide + a reduced glutaredoxin

guaiacylglycerol-β-guaiacyl ether degradation :
α-glutathionyl-β-hydroxypropiovanillone I + glutathione → β-hydroxypropiovanillone + glutathione disulfide
α-glutathionyl-β-hydroxypropiovanillone II + glutathione → β-hydroxypropiovanillone + glutathione disulfide

pentachlorophenol degradation :
2,3,6-trichlorohydroquinone + 2 glutathione → 2,6-dichloro-p-hydroquinone + chloride + glutathione disulfide + H+

reactive oxygen species degradation (mammalian) :
hydrogen peroxide + 2 glutathione → glutathione disulfide + 2 H2O

selenate reduction :
selenite + 4 glutathione + 2 H+ → selenodiglutathione + glutathione disulfide + 3 H2O
selenite + AMP + glutathione disulfide + 3 H+ ← adenosine 5'-phosphoselenate + 2 glutathione

sulfate reduction II (assimilatory) :
sulfite + AMP + glutathione disulfide + 2 H+ ← adenosine 5'-phosphosulfate + 2 glutathione

Not in pathways:
2 glutathione + oxygen → glutathione disulfide + hydrogen peroxide

Reactions known to both consume and produce the compound:

γ-hexachlorocyclohexane degradation :
2,5-dichloro-p-quinol + 2 glutathione ↔ chlorohydroquinone + glutathione disulfide + chloride + H+

pentachlorophenol degradation :
tetrachlorohydroquinone + 2 glutathione ↔ 2,3,6-trichlorohydroquinone + chloride + glutathione disulfide

In Reactions of unknown directionality:

Not in pathways:
L-cystine + 2 glutathione = glutathione disulfide + 2 L-cysteine
homocystine + 2 glutathione = glutathione disulfide + 2 L-homocysteine
2 glutathione + a protein disulfide = glutathione disulfide + a protein dithiol
2-hydroxyethyldisulfide + 2 glutathione = 2 2-mercaptoethanol + glutathione disulfide
thiosulfate + 2 glutathione = sulfite + hydrogen sulfide + glutathione disulfide + H+
GS-methylhydroquinone + glutathione = methyl-p-hydroquinone + glutathione disulfide
D-cystine + 2 glutathione = glutathione disulfide + 2 D-cysteine
chloride + glutathione disulfide + benzene-1,4-diol + H+ = chlorohydroquinone + 2 glutathione
a xanthine dehydrogenase + glutathione disulfide = a xanthine oxidase + 2 glutathione
glutathione disulfide + coenzyme A = glutathione + CoA-glutathione

Enzymes inhibited by glutathione disulfide, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: maleylacetoacetate isomerase [Morrison76]

Inhibitor (Mechanism unknown) of: glutathione reductase [Mata84, Comment 1] , glutathione synthetase [Apontoweil75] , phosphoprotein phosphatase [Rao02] , γ-glutamyl transpeptidase [Miller76a] , guanidinoacetate methyltransferase [Konishi91] , triose-phosphate isomerase [Ito03]

Credits:
Revised 12-Mar-2012 by Caspi R , SRI International


References

Apontoweil75: Apontoweil P, Berends W (1975). "Glutathione biosynthesis in Escherichia coli K 12. Properties of the enzymes and regulation." Biochim Biophys Acta 1975;399(1);1-9. PMID: 238647

Ito03: Ito H, Iwabuchi M, Ogawa K (2003). "The sugar-metabolic enzymes aldolase and triose-phosphate isomerase are targets of glutathionylation in Arabidopsis thaliana: detection using biotinylated glutathione." Plant Cell Physiol 44(7);655-60. PMID: 12881492

Konishi91: Konishi K, Fujioka M (1991). "Reversible inactivation of recombinant rat liver guanidinoacetate methyltransferase by glutathione disulfide." Arch Biochem Biophys 289(1);90-6. PMID: 1898065

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Mata84: Mata AM, Pinto MC, Lopez-Barea J (1984). "Purification by affinity chromatography of glutathione reductase (EC 1.6.4.2) from Escherichia coli and characterization of such enzyme." Z Naturforsch [C] 39(9-10);908-15. PMID: 6393625

Miller76a: Miller SP, Awasthi YC, Srivastava SK (1976). "Studies of human kidney gamma-glutamyl transpeptidase. Purification and structural, kinetic and immunological properties." J Biol Chem 251(8);2271-8. PMID: 4442

Morrison76: Morrison WS, Wong G, Seltzer S (1976). "Maleylacetone cis-trans-isomerase: affinity chromatography on glutathione-bound sepharose. Two-substrate-binding sequence from inhibition patterns." Biochemistry 15(19);4228-33. PMID: 963032

Rao02: Rao RK, Clayton LW (2002). "Regulation of protein phosphatase 2A by hydrogen peroxide and glutathionylation." Biochem Biophys Res Commun 293(1);610-6. PMID: 12054646


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Nov 20, 2014, BIOCYC14B.