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Information on EC 3.1.2.6 - hydroxyacylglutathione hydrolase
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3.1.2.6 hydroxyacylglutathione hydrolaseIUBMB Comments
Also hydrolyses S-acetoacetylglutathione, but more slowly.
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Word Map
- 3.1.2.6
- methylglyoxal
- gsh
- s-d-lactoylglutathione
-
glyoxalases
- d-lactate
-
glycation
-
glutathione-dependent
- dehydroascorbate
- monodehydroascorbate
- hemithioacetal
-
d-lactic
- mdhar
-
dicarbonyls
- trypanothione
- 2-oxoaldehydes
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4.4.1.5
- lactoylglutathione
- metallo-beta-lactamase
- drug development
- biotechnology
- pharmacology
- medicine
- agriculture
The enzyme appears in viruses and cellular organisms
Synonyms
glyoxalase ii, glyoxalase 2, gly ii, glyii, glxii, glx2-2, gloii, hydroxyacylglutathione hydrolase, cgloii, glo ii, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acetoacetylglutathione hydrolase
EC 3.1.2.8
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formerly
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Germ cell specific protein
GLO II
Glo2
GloB
Glx II
GLX2
GLX2-2
GlxII
Gly II
GLYII
glyoxalase II
glyoxylase II
hydrolase, acetoacetylglutathione
hydrolase, hydroxyacylglutathione
hydroxyacylglutathione hydrolase
Round spermatid protein RSP29
S-2-hydroxylacylglutathione hydrolase
additional information
acetoacetylglutathione hydrolase
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Germ cell specific protein
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GLO II
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glyoxalase II
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hydrolase, acetoacetylglutathione
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hydrolase, hydroxyacylglutathione
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hydroxyacylglutathione hydrolase
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Round spermatid protein RSP29
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S-2-hydroxylacylglutathione hydrolase
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additional information
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the enzyme belongs to the metallo-beta-lactamase superfamily
additional information
enzyme belongs to the metallo-beta-lactamase superfamily
additional information
enzyme is a member of the zinc metallohydrolase family with a beta-lactamase fold
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-(2-hydroxyacyl)glutathione + H2O = glutathione + a 2-hydroxy carboxylate
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S-(2-hydroxyacyl)glutathione + H2O = glutathione + a 2-hydroxy carboxylate
mechanism
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S-(2-hydroxyacyl)glutathione + H2O = glutathione + a 2-hydroxy carboxylate
reaction mechanism
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S-(2-hydroxyacyl)glutathione + H2O = glutathione + a 2-hydroxy carboxylate
active site and reaction mechanism
S-(2-hydroxyacyl)glutathione + H2O = glutathione + a 2-hydroxy carboxylate
active site residue Tyr175 contributes to the binding of glutathione derivatives by its hydroxyl group which forms hydrogen binds to the glycine in the glutathione moiety
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of thioester
hydrolysis of thioester
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
S-(2-hydroxyacyl)glutathione hydrolase
Also hydrolyses S-acetoacetylglutathione, but more slowly.
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CAS REGISTRY NUMBER
COMMENTARY
9025-90-5
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9025-92-7
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
bis(pivaloyloxymethyl)(1-hydroxy-2-oxopiperidin-3-yl)phosphonate + H2O
[[(hydroxymethoxy)(1-hydroxy-2-oxopiperidin-3-yl)phosphoryl]oxy]methyl 2,2-dimethylpropanoate + 2,2-dimethylpropanoate
i.e. POM-HEX, substrate is a prodrug of the compound HEX, which inhibits the glycolytic enzyme enolase
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?
bis-(lactoyl)trypanothione + H2O
trypanothione + D-lactate
preferred substrate
trypathione is bis(glutathionyl)spermidine
?
fluorescein-3',6'-bis(oxy)methylene bis(2-methoxypropanoate) + H2O
fluorescein-3'-oxymethyl 2-methoxypropanoate + 2-methoxypropanoate
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?
fluorescein-3',6'-bis(oxy)methylene bis(ethoxyacetate) + H2O
fluorescein-3'-yoxymethyl ethoxyacetate + ethoxyacetate
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?
fluorescein-3',6'-bis(oxy)methylene bis(methoxyacetate) + H2O
fluorescein-3'-oxymethyl methoxyacetate + methoxyacetate
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?
fluorescein-3',6'-bis(oxy)methylene bis(propoxyacetate) + H2O
fluorescein-3'-oxymethyl propoxyacetate + propoxyacetate
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?
fluorescein-3',6'-bis(oxy)methylene bis[(ethylsulfanyl)acetate] + H2O
fluorescein-3'-oxymethyl (ethylsulfanyl)acetate + (ethylsulfanyl)acetate
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?
fluorescein-3',6'-bis(oxy)methylene bis[(methylsulfanyl)acetate] + H2O
fluorescein-3'-oxymethyl (methylsulfanyl)acetate + (methylsulfanyl)acetate
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?
fluorescein-3',6'-bis(oxy)methylene dibutanoate + H2O
fluorescein-3'-oxymethyl butanoate + butanoate
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?
fluorescein-3',6'-bis(oxy)methylene dihexanoate + H2O
fluorescein-3'-oxymethyl hexanoate + hexanoate
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?
fluorescein-3',6'-bis(oxy)methylene dipentanoate + H2O
fluorescein-3'-oxymethyl pentanoate + pentanoate
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?
mono-(lactoyl)trypanothione + H2O
trypanothione + D-lactate
preferred substrate
trypathione is bis(glutathionyl)spermidine
?
N,S-bisfluorenylmethoxycarbonylglutathione + H2O
9-fluorenylmethoxycarboxylate + glutathione
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?
S-(beta-ethoxy-alpha-D-hydroxybutyryl)glutathione + H2O
beta-ethoxy-alpha-D-hydroxybutyrate + glutathione
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?
S-(N-hydroxy-N-bromophenylcarbamoyl)glutathione + H2O
?
slow model substrate for computational study, the substrate does not coordinate to any of the zinc ions in the Michaelis complex. The hydroxyl group forms a hydrogen bond to the Asp58 residue.
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?
S-(N-hydroxy-N-bromophenylcarbamoyl)glutathione + H2O
N-hydroxy-N-bromophenylcarbamate + glutathione
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weak substrate
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?
S-bis-lactoyltrypanothione + 2 H2O
2 D-lactate + trypanothione
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?
S-D-lactoylglutathione
D-lactate + glutathione
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?
S-D-lactoylglutathione + H2O
D-lactic acid + glutathione
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?
S-D-lactoyltrypanothione + H2O
D-lactate + trypanothione
additionally S-D-lactoylglutathione used by mutant Y291R/C294K
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?
S-glycolylglutathione + H2O
? + glutathione
hydrolysis at about half the rate of S-lactoylglutathione
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?
S-hydroxyglutaryltrypanothione + H2O
hydroxyglutarate + trypanothione + 2 H+
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?
S-lactonylglutathione + H2O
? + glutathione
hydrolysis about 10fold lower than of S-lactoylglutathione
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?
S-m-nitrobenzyloxycarbonylglutathione + H2O
m-nitrobenzyloxycarboxylate + glutathione
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?
S-mandeloylglutathione + H2O
mandelic acid + glutathione
hydrolysis about 10fold lower than of S-lactoylglutathione
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?
S-o-nitrobenzyloxycarbonylglutathione + H2O
o-nitrobenzyloxycarboxylate + glutathione
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?
S-p-nitrobenzyloxycarbonylglutathione + H2O
p-nitrobenzyloxycarboxylate + glutathione
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?
S-propionyltrypanothione + H2O
propionate + trypanothione + H+
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?
(S)-D-lactoylglutathione + H2O
D-lactate + glutathione
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?
lactoylglutathione + H2O
D-lactate + glutathione
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S-D-lactoylglutathione
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?
lactoylglutathione + H2O
D-lactate + glutathione
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S-D-lactoylglutathione
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?
lactoylglutathione + H2O
D-lactate + glutathione
little activity with this substrate
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?
lactoylglutathione + H2O
D-lactate + glutathione
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?
lactoylglutathione + H2O
D-lactate + glutathione
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?
lactoylglutathione + H2O
D-lactate + glutathione
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reaction is rate-limiting, methylglyoxal bypass of glycolysis
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r
lactoylglutathione + H2O
D-lactate + glutathione
enzyme does not show saturation kinetics up to 5 mM
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?
mono-(lactoyl)trypanothione + H2O
D-lactate + trypanothione
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?
mono-(lactoyl)trypanothione + H2O
D-lactate + trypanothione
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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enzyme is part of the glyoxalase system and involved in detoxification of methylglyoxal
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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enzyme is part of the glyoxalase system and involved in detoxification of methylglyoxal
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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second step in the glyoxalase system
regeneration of glutathione for the first step in the glyoxalase system
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ir
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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the enzyme is involved in the detoxification process converting reactive dicarbonyl compounds such as methylglyoxal to less reactive hydroxyl acids
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?
S-(2-hydroxyacyl)glutathione + H2O
glutathione + a 2-hydroxycarboxylate anion
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?
S-acetoacetylglutathione + H2O
acetoacetate + glutathione
hydrolysis at about half the rate of S-lactoylglutathione
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?
S-acetoacetylglutathione + H2O
acetoacetate + glutathione
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55.6% of the activity with S-lactoylglutathione
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?