fbpx
Wikipedia

Glutathione disulfide

Glutathione disulfide (GSSG) is a disulfide derived from two glutathione molecules.[1]

Glutathione disulfide
Names
Systematic IUPAC name
(2S,2′S)-5,5′-(Disulfanediylbis{(2R)-3-[(carboxymethyl)amino]-3-oxopropane-1,2-diyl})bis(2-amino-5-oxopentanoic acid)
Identifiers
  • 27025-41-8 Y
3D model (JSmol)
  • Interactive image
Abbreviations GSSG
ChEMBL
  • ChEMBL1372 N
ChemSpider
  • 58835 N
ECHA InfoCard 100.043.777
  • 6835
KEGG
  • C00127
  • 65359
  • 11215652
UNII
  • ULW86O013H Y
  • DTXSID5048972
  • 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 612.63 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

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

The GSH:GSSG ratio is therefore an important bioindicator of cellular health, with a higher ratio signifying less oxidative stress in the organism. A lower ratio may even be indicative of neurodegenerative diseases, such as Parkinson's disease (PD) and Alzheimer's disease.[5]

Neuromodulator edit

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.[6][7] At millimolar concentrations, they may also modulate the redox state of the NMDA receptor complex.[7]

See also edit

References edit

  1. ^ Meister A, Anderson ME (1983). "Glutathione". Annual Review of Biochemistry. 52: 711–60. doi:10.1146/annurev.bi.52.070183.003431. PMID 6137189.
  2. ^ Deneke SM, Fanburg BL (1989). "Regulation of cellular glutathione". The American Journal of Physiology. 257 (4 Pt 1): L163–73. doi:10.1152/ajplung.1989.257.4.L163. PMID 2572174.
  3. ^ Meister A (1988). "Glutathione metabolism and its selective modification". The Journal of Biological Chemistry. 263 (33): 17205–8. doi:10.1016/S0021-9258(19)77815-6. 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. ^ Owen, Joshua B.; Butterfield, D. Allan (2010). "Measurement of oxidized/reduced glutathione ratio". In Bross, Peter; Gregersen, Niels (eds.). Protein Misfolding and Cellular Stress in Disease and Aging. Methods in Molecular Biology. Vol. 648. pp. 269–77. doi:10.1007/978-1-60761-756-3_18. ISBN 978-1-60761-755-6. PMID 20700719.
  6. ^ Steullet P, Neijt HC, Cuénod M, Do KQ (2006). "Synaptic plasticity impairment and hypofunction of NMDA receptors induced by glutathione deficit: relevance to schizophrenia". Neuroscience. 137 (3): 807–19. doi:10.1016/j.neuroscience.2005.10.014. PMID 16330153. S2CID 1417873.
  7. ^ a b Varga V, Jenei Z, Janáky R, Saransaari P, Oja SS (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): 1165–71. doi:10.1023/A:1027377605054. PMID 9251108. S2CID 24024090.

glutathione, disulfide, gssg, disulfide, derived, from, glutathione, molecules, names, systematic, iupac, name, disulfanediylbis, carboxymethyl, amino, oxopropane, diyl, amino, oxopentanoic, acid, identifiers, number, 27025, model, jsmol, interactive, image, a. Glutathione disulfide GSSG is a disulfide derived from two glutathione molecules 1 Glutathione disulfide Names Systematic IUPAC name 2S 2 S 5 5 Disulfanediylbis 2R 3 carboxymethyl amino 3 oxopropane 1 2 diyl bis 2 amino 5 oxopentanoic acid Identifiers CAS Number 27025 41 8 Y 3D model JSmol Interactive image Abbreviations GSSG ChEMBL ChEMBL1372 N ChemSpider 58835 N ECHA InfoCard 100 043 777 IUPHAR BPS 6835 KEGG C00127 PubChem CID 6535911215652 UNII ULW86O013H Y CompTox Dashboard EPA DTXSID5048972 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 NKey YPZRWBKMTBYPTK BJDJZHNGSA N NInChI 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 s1Key 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 C 20H 32N 6O 12S 2 Molar mass 612 63 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 The GSH GSSG ratio is therefore an important bioindicator of cellular health with a higher ratio signifying less oxidative stress in the organism A lower ratio may even be indicative of neurodegenerative diseases such as Parkinson s disease PD and Alzheimer s disease 5 Neuromodulator editGSSG 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 g glutamyl moieties and may be endogenous neuromodulators 6 7 At millimolar concentrations they may also modulate the redox state of the NMDA receptor complex 7 See also editGlutathione ascorbate cycle AntioxidantReferences edit Meister A Anderson ME 1983 Glutathione Annual Review of Biochemistry 52 711 60 doi 10 1146 annurev bi 52 070183 003431 PMID 6137189 Deneke SM Fanburg BL 1989 Regulation of cellular glutathione The American Journal of Physiology 257 4 Pt 1 L163 73 doi 10 1152 ajplung 1989 257 4 L163 PMID 2572174 Meister A 1988 Glutathione metabolism and its selective modification The Journal of Biological Chemistry 263 33 17205 8 doi 10 1016 S0021 9258 19 77815 6 PMID 3053703 Holmgren A Johansson C Berndt C Lonn 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 Owen Joshua B Butterfield D Allan 2010 Measurement of oxidized reduced glutathione ratio In Bross Peter Gregersen Niels eds Protein Misfolding and Cellular Stress in Disease and Aging Methods in Molecular Biology Vol 648 pp 269 77 doi 10 1007 978 1 60761 756 3 18 ISBN 978 1 60761 755 6 PMID 20700719 Steullet P Neijt HC Cuenod M Do KQ 2006 Synaptic plasticity impairment and hypofunction of NMDA receptors induced by glutathione deficit relevance to schizophrenia Neuroscience 137 3 807 19 doi 10 1016 j neuroscience 2005 10 014 PMID 16330153 S2CID 1417873 a b Varga V Jenei Z Janaky R Saransaari P Oja SS 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 71 doi 10 1023 A 1027377605054 PMID 9251108 S2CID 24024090 Retrieved from https en wikipedia org w index php title Glutathione disulfide amp oldid 1152832328, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.