Information on EC 1.8.5.7 - glutathionyl-hydroquinone reductase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.8.5.7
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RECOMMENDED NAME
GeneOntology No.
glutathionyl-hydroquinone reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
glutathione + 2-(glutathione-S-yl)-hydroquinone = glutathione disulfide + hydroquinone
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
pentachlorophenol degradation
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SYSTEMATIC NAME
IUBMB Comments
2-(glutathione-S-yl)-hydroquinone:glutathione oxidoreductase
This type of enzymes, which are found in bacteria, halobacteria, fungi, and plants, catalyse the glutathione-dependent reduction of glutathionyl-hydroquinones. The enzyme from the bacterium Sphingobium chlorophenolicum can act on halogenated substrates such as 2,6-dichloro-3-(glutathione-S-yl)-hydroquinone and 2,3,5-trichloro-6-(glutathione-S-yl)-hydroquinone. Substrates for these enzymes are often formed spontaneously by interaction of benzoquinones with glutathione.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-mercaptoethanol + 2-(glutathione-S-yl)-trichloro-p-hydroquinone
glutathionyl 2-mercaptoethanyl disulfide + trichloro-p-hydroquinone
show the reaction diagram
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?
dithiothreitol + 2-(glutathione-S-yl)-trichloro-p-hydroquinone
glutathionyl dithiotreityl disulfide + trichloro-p-hydroquinone
show the reaction diagram
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?
glutathione + (glutathione-S-yl)-2-chloro-1,4-benzoquinone
glutathione disulfide + 2-chloro-1,4-benzoquinone
show the reaction diagram
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-
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?
glutathione + 2-(glutathione-S-yl)-1,4-benzoquinone
glutathione disulfide + 1,4-benzoquinone
show the reaction diagram
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?
glutathione + 2-(glutathione-S-yl)-dichloro-p-hydroquinone
glutathione disulfide + dichloro-p-hydroquinone
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-hydroquinone
glutathione disulfide + hydroquinone
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-hydroxy-p-hydroquinone
glutathione disulfide + hydroxy-p-hydroquinone
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-menadiol
glutathione disulfide + menadiol
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-menadiol
glutathione disulfide + menadione
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-menadione
glutathione disulfide + menadione
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-methyl-p-hydroquinone
glutathione disulfide + methyl-p-hydroquinone
show the reaction diagram
glutathione + 2-(glutathione-S-yl)-quercetin
glutathione disulfide + quercetin
show the reaction diagram
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-
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?
glutathione + 2-(glutathione-S-yl)-trichloro-p-hydroquinone
glutathione disulfide + trichloro-p-hydroquinone
show the reaction diagram
L-cysteine + 2-(glutathione-S-yl)-trichloro-p-hydroquinone
glutathionyl cysteinyl disulfide + trichloro-p-hydroquinone
show the reaction diagram
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
glutathione + 2-(glutathione-S-yl)-hydroquinone
glutathione disulfide + hydroquinone
show the reaction diagram
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?
additional information
?
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PcpF catalyzes glutathione-dependent reduction of glutathionyl-trichloro-p-hydroquinone via a Ping Pong mechanism. First, PcpF reacts with glutathionyl-trichloro-p-hydroquinone to release trichloro-p-hydroquinone and forms a disulfide bond between its Cys53 residue and the glutathione moiety. Then, a glutathione comes in to regenerate PcpF and release glutathione disulfide
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.072
(glutathione-S-yl)-2-chloro-1,4-benzoquinone
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wild-type, pH 8.0, 20C
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0.0926
2-(glutathione-S-yl)-1,4-benzoquinone
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wild-type, pH 8.0, 20C
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0.24 - 0.43
2-(glutathione-S-yl)-hydroquinone
0.012 - 0.13
2-(glutathione-S-yl)-hydroxy-p-hydroquinone
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0.003 - 0.017
2-(glutathione-S-yl)-menadiol
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0.27
2-(glutathione-S-yl)-menadione
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wild-type, pH 8.0, 20C
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0.034 - 0.19
2-(glutathione-S-yl)-methyl-p-hydroquinone
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0.0027
2-(glutathione-S-yl)-quercetin
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wild-type, pH 8.0, 20C
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0.0044
2-(glutathione-S-yl)-trichloro-p-hydroquinone
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pH 6.5, 30C
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0.93
2-mercaptoethanol
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pH 6.5, 30C
0.26
dithiothreitol
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pH 6.5, 30C
0.35 - 1.3
glutathione
1.97
L-cysteine
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pH 6.5, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7.96
(glutathione-S-yl)-2-chloro-1,4-benzoquinone
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wild-type, pH 8.0, 20C
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1.62
2-(glutathione-S-yl)-1,4-benzoquinone
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wild-type, pH 8.0, 20C
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11 - 22
2-(glutathione-S-yl)-hydroquinone
4.4 - 19
2-(glutathione-S-yl)-hydroxy-p-hydroquinone
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4.6 - 14
2-(glutathione-S-yl)-menadiol
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4.75
2-(glutathione-S-yl)-menadione
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wild-type, pH 8.0, 20C
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8.4 - 31
2-(glutathione-S-yl)-methyl-p-hydroquinone
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0.013
2-(glutathione-S-yl)-quercetin
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wild-type, pH 8.0, 20C
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1.09
2-mercaptoethanol
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pH 6.5, 30C
0.89
dithiothreitol
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pH 6.5, 30C
2.08 - 37
glutathione
0.37
L-cysteine
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pH 6.5, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
110.6
(glutathione-S-yl)-2-chloro-1,4-benzoquinone
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wild-type, pH 8.0, 20C
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17.5
2-(glutathione-S-yl)-1,4-benzoquinone
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wild-type, pH 8.0, 20C
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26 - 91
2-(glutathione-S-yl)-hydroquinone
15 - 590
2-(glutathione-S-yl)-hydroxy-p-hydroquinone
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760 - 3215
2-(glutathione-S-yl)-menadiol
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17.4
2-(glutathione-S-yl)-menadione
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wild-type, pH 8.0, 20C
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56 - 410
2-(glutathione-S-yl)-methyl-p-hydroquinone
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4.95
2-(glutathione-S-yl)-quercetin
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wild-type, pH 8.0, 20C
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1.17
2-mercaptoethanol
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pH 6.5, 30C
3.43
dithiothreitol
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pH 6.5, 30C
1.6 - 42
glutathione
0.19
L-cysteine
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pH 6.5, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.16
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mutant Y253F, pH 7.5, temperature not specified in the publication
0.19
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mutant Y195F, pH 7.5, temperature not specified in the publication
0.4
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mutant Y296F, pH 7.5, temperature not specified in the publication
8.65
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wild-type, pH 7.5, temperature not specified in the publication
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 36900, calculated
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
binary complex structure with glutathionyl-menadione. The structure reveals a large H-site that could accommodate various substituted hydroquinones and a hydrogen network of three Tyr residues that could provide the proton for reductive deglutathionylation
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structure in complex with glutathione, to 2.5 A resolution. Isoform GHR1 adopts a typical glutathionyl-hydroquinone reductase fold, with a dimerization interface comparable to that of the bacterial and fungal counterparts
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isoform ECM4 shows extensions including a huge loop which contributes to the quaternary assembly. Soaking of ECM4 crystals with glutathionyl-menadione results in a structure where glutathione forms a mixed disulfide bond with the cysteine 46. Residues H345 and H350, F228, Y224 and W48 could play crucial roles in binding of glutathionyl-(hydro)quinones, and in assisting C46 during catalysis
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C63A
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catalytic residue, mutant displays negligible activity
Y195F
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catalytic residue, mutant displays negligible activity
Y253F
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catalytic residue, mutant displays negligible activity
Y296F
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catalytic residue, mutant displays negligible activity
C49A
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mutation of catalytic cysteine, loss of activity
C49S
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mutation of catalytic cysteine, loss of activity