Information on EC 4.4.1.5 - lactoylglutathione lyase

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

EC NUMBER
COMMENTARY hide
4.4.1.5
-
RECOMMENDED NAME
GeneOntology No.
lactoylglutathione lyase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(R)-S-lactoylglutathione = glutathione + methylglyoxal
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
addition
isomerization
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-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
methylglyoxal degradation
-
-
methylglyoxal degradation I
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-
Pyruvate metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
(R)-S-lactoylglutathione methylglyoxal-lyase (isomerizing; glutathione-forming)
Also acts on 3-phosphoglycerol-glutathione.
CAS REGISTRY NUMBER
COMMENTARY hide
9033-12-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Amaranthus sp.
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-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
5177D mt-
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-
Manually annotated by BRENDA team
5177D mt-
-
-
Manually annotated by BRENDA team
IFO 0895
-
-
Manually annotated by BRENDA team
immature specimen
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-
Manually annotated by BRENDA team
Escherichia coli MG1655/pGL10
MG1655/pGL10
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
IL1404
UniProt
Manually annotated by BRENDA team
IL1404
UniProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
no activity in Entamoeba histolytica
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-
-
Manually annotated by BRENDA team
no activity in Giardia lamblia
-
-
-
Manually annotated by BRENDA team
no activity in Trypanosoma brucei
causative agent of onchocerciasis, GloI expression is induced by oxidative stress
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
strain SN15
SwissProt
Manually annotated by BRENDA team
strain SN15
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
crayfish, adult, female and male
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-
Manually annotated by BRENDA team
DKD-5D-H
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-
Manually annotated by BRENDA team
strain YPH250
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-
Manually annotated by BRENDA team
PR 109
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain UA159
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Manually annotated by BRENDA team
strain UA159
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-S-lactoylglutathione
glutathione + methylglyoxal
show the reaction diagram
gamma-glutamylcysteine-methylglyoxal hemithioacetal
?
show the reaction diagram
gamma-glutamylcysteine-methylglyoxal hemithioacetal is formed non-enzymatically from methylglyoxal and glutathione
-
?
gamma-glutamylcysteine-phenylglyoxal hemithioacetal
?
show the reaction diagram
gamma-glutamylcysteine-phenylglyoxal hemithioacetal is formed non-enzymatically from methylglyoxal and glutathione
-
?
glutathione + 2,4-dimethylphenylglyoxal
S-(2,4-dimethyl)mandeloylglutathione
show the reaction diagram
-
-
-
-
?
glutathione + 4,5-dioxovalerate
?
show the reaction diagram
glutathione + bromophenylglyoxal
?
show the reaction diagram
-
-
-
-
?
glutathione + glyoxal
S-glycolylglutathione
show the reaction diagram
glutathione + hydroxypyruvaldehyde
?
show the reaction diagram
-
-
-
-
?
glutathione + kethoxal
?
show the reaction diagram
glutathione + m-methoxyphenylglyoxal
S-(3-methoxy)mandeloylglutathione
show the reaction diagram
-
-
-
-
?
glutathione + methylglyoxal
(R)-S-lactoylglutathione
show the reaction diagram
glutathione + methylglyoxal
?
show the reaction diagram
glutathione + methylglyoxal
S-((R)-lactoyl)glutathione
show the reaction diagram
glutathione + methylglyoxal
S-D-lactoylglutathione
show the reaction diagram
glutathione + methylglyoxal
S-lactoylglutathione
show the reaction diagram
glutathione + methylphenylglyoxal
?
show the reaction diagram
-
-
-
-
?
glutathione + p-chlorophenylglyoxal
S-(4-chloro)mandeloylglutathione
show the reaction diagram
glutathione + p-hydroxyphenylglyoxal
S-(4-hydroxy)mandeloylglutathione
show the reaction diagram
-
-
-
-
?
glutathione + p-methoxyphenylglyoxal
S-(4-methoxy)mandeloylglutathione
show the reaction diagram
-
-
-
-
?
glutathione + p-phenylphenylglyoxal
?
show the reaction diagram
-
-
-
-
?
glutathione + phenylglyoxal
S-mandeloylglutathione
show the reaction diagram
glutathione + phenylglyoxal
S-mandoylglutathione
show the reaction diagram
-
-
-
-
?
glutathione-glyoxal hemithioacetal
?
show the reaction diagram
-
-
?
glutathione-methylglyoxal hemithioacetal
(R)-S-lactoylglutathione
show the reaction diagram
glutathione-phenylglyoxal hemithioacetal
?
show the reaction diagram
glutathionylspermidine + methylglyoxal
?
show the reaction diagram
glutathionylspermidine + phenylglyoxal
?
show the reaction diagram
-
-
-
-
?
hemithioacetal + glutathione
(S)-D-lactoylglutathione
show the reaction diagram
-
-
-
-
?
hemithioacetal + reduced trypanothione
(S)-D-lactoyltrypanothione
show the reaction diagram
-
-
-
?
homoglutathione-methylglyoxal hemithioacetal
(R)-S-lactoylhomoglutathione
show the reaction diagram
homoglutathione-methylglyoxal hemithioacetal is formed non-enzymatically from methylglyoxal and glutathione
-
?
homoglutathione-phenylglyoxal hemithioacetal
?
show the reaction diagram
homoglutathione-phenylglyoxal hemithioacetal is formed non-enzymatically from methylglyoxal and glutathione
-
?
methylglyoxal + glutathione
(R)-S-lactoylglutathione
show the reaction diagram
methylglyoxal + glutathione
(R)S-lactoylglutathione
show the reaction diagram
Amaranthus sp.
-
first step in the glyoxalase system
-
-
r
methylglyoxal + glutathione
S-((R)-lactoyl)glutathione
show the reaction diagram
methylglyoxal + trypanothione
S,S'-bis((R)-lactoyl)trypanothione
show the reaction diagram
N1-glutathionylspermidine + methylglyoxal
?
show the reaction diagram
S-D-lactoyltrypanothione
methylglyoxal + reduced trypanothione
show the reaction diagram
-
-
-
?
S-mandoylglutathione
glutathione + phenylglyoxal
show the reaction diagram
-
-
-
?
S-mandoyltrypanothione
phenylglyoxal + trypanothione
show the reaction diagram
-
-
-
?
trypanothione + 2 methylglyoxal
5,5'-bi((R)-lactoyl)trypanothione
show the reaction diagram
trypanothione + methylglyoxal
(R)-S-lactoylglutathione
show the reaction diagram
trypanothione + methylglyoxal
5,5'-bi((R)-lactoyl)trypanothione
show the reaction diagram
trypanothione + methylglyoxal
S,S'-bis((R)-lactoyl)trypanothione
show the reaction diagram
trypanothione + phenylglyoxal
S-mandoyltrypanothione
show the reaction diagram
-
-
-
-
?
additional information
?
-
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 + methylglyoxal
(R)-S-lactoylglutathione
show the reaction diagram
glutathione + methylglyoxal
?
show the reaction diagram
glutathione-glyoxal hemithioacetal
?
show the reaction diagram
Q71KM3
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-
?
glutathione-methylglyoxal hemithioacetal
(R)-S-lactoylglutathione
show the reaction diagram
glutathionylspermidine + methylglyoxal
?
show the reaction diagram
-
-
-
-
-
methylglyoxal + glutathione
(R)-S-lactoylglutathione
show the reaction diagram
methylglyoxal + glutathione
(R)S-lactoylglutathione
show the reaction diagram
Amaranthus sp.
-
first step in the glyoxalase system
-
-
r
methylglyoxal + glutathione
S-((R)-lactoyl)glutathione
show the reaction diagram
-
glyoxalase I is a member of the metallogltathione transferase superfamily and plays a critical role in detoxification of the cytotoxic methylglyoxal to S-D-lactoylglutathione via 1,2-hydrogen transfer
-
-
?
trypanothione + 2 methylglyoxal
5,5'-bi((R)-lactoyl)trypanothione
show the reaction diagram
-
-
-
-
?
trypanothione + methylglyoxal
(R)-S-lactoylglutathione
show the reaction diagram
-
-
-
-
?
trypanothione + methylglyoxal
5,5'-bi((R)-lactoyl)trypanothione
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
glutathione
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CuSO4
0.2 mM, extracellular, 30fold upregulated protein spot in the 2D-electrophoresis, identified as glyoxalase I, the expression is regulated by the operon yahCD-yaiAB
Fe3+
-
activation of gly I
methylglyoxal
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10 mM, enhanced tolerance to toxic stress in transgenic Vigna mungo
NaCl
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the transgenic and the untransformed plants are exposed to 100 mM NaCl. The transgenic plants survived whereas the untransformed control plants fail to survive
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1E,4Z,6E)-4-(4-hydroxy-3-methoxybenzylidene)-1-(3-hydroxy-4-methoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
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three-ring curcumin derivative, in binding model two rings lay in the opening of the active site, the third is buried into hydrophobic pocket site
(1E,6E)-4-(3,4-dimethoxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
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three-ring curcumin derivative, in binding model two rings lay in the opening of the active site, the third is buried into hydrophobic pocket site
(1E,6E)-4-(3-fluorobenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
-
three-ring curcumin derivative, in binding model two rings lay in the opening of the active site, the third is buried into hydrophobic pocket site
(1E,6E)-4-(4-fluorobenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
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three-ring curcumin derivative, in binding model two rings lay in the opening of the active site, the third is buried into hydrophobic pocket site
(2S)-2-amino-3-[([(2R)-3-[(4-bromobenzyl)sulfanyl]-1-[(carboxymethyl)amino]-1-oxopropan-2-yl]carbamoyl)amino]propanoic acid
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(3Z)-3-(1,3-benzothiazol-2-yl)-4-(4-methoxyphenyl)but-3-enoic acid
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inhibitor based on binding mode of myricetin, contributuion of the Zn2+-chelating group to inhibitory activity
(S)-4-bromobenzyl glutathione
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potent Glx-I inhibitor
(S)-4-bromobenzylglutathione cyclopentyl diester
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competitive inhibitor of GLOI
(Z)-1-[N-(2-aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate
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decreases glyoxalase I expression and activity relative to untreated control cells, cells undergo apoptosis, apoptosis increases further on co-incubation with high glucose
1'-hydroxy-6'-phenyl-3,4'-bipyridin-2'(1'H)-one
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1,10-phenanthroline
1-chloro-2,4-dinitrobenzene
-
not reduced by dithiothreitol
1-ethyl-3-(3-dimethylaminopropyl) carbodiimide
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10 mM, 65% inhibition
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
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1-hydroxy-4,6-diphenylpyridin-2(1H)-one
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1-hydroxy-4-phenyl-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2(1H)-one
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1-hydroxy-6-(1-pentyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-4-phenylpyridin-2(1H)-one
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1-hydroxy-6-(1H-indol-5-yl)-4-phenylpyridin-2(1H)-one
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1-hydroxy-6-phenyl-4-(thiophen-3-yl)pyridin-2(1H)-one
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1-hydroxy-6-phenyl-4-[4-(trifluoromethyl)phenyl]pyridin-2(1H)-one
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1-hydroxy-6-[1-(2-methoxyethyl)-1H-indol-5-yl]-4-phenylpyridin-2(1H)-one
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1-hydroxy-6-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-4-phenylpyridin-2(1H)-one
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1-hydroxy-6-[1-(3-methoxypropyl)-1H-indol-5-yl]-4-phenylpyridin-2(1H)-one
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1-hydroxy-6-[1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-4-phenylpyridin-2(1H)-one
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1-Naphthaleneacetic acid
2,2'-dipyridyl
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2,3-Butanedione
-
time and concentration dependent inactivation
2,3-Dihydroxybenzoic acid
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2,4,6-Trinitrobenzenesulfonic acid
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2,4,6-trinnitrobenzenesulphonic acid
-
2 mM, 60% inhibition
2,6-pyridindicarboxylic acid
-
2 mM, approx. 50% inactivation after 10 min, almost complete inhibition after 180 min
2-([(4-methoxyphenyl)carbonyl]amino)-1-benzothiophene-3-carboxylic acid
-
inhibitor based on binding mode of myricetin
2-([(4-methoxyphenyl)carbonyl]amino)benzoic acid
-
inhibitor based on binding mode of myricetin
2-aminopyridine
-
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2-Hydroxy-5-nitrobenzyl bromide
-
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3-hydroxyflavone
-
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3-[[5-(1-hydroxy-6-oxo-4-phenyl-1,6-dihydropyridin-2-yl)-1H-indol-1-yl]methyl]benzamide
-
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3-[[5-(1-hydroxy-6-oxo-4-phenyl-1,6-dihydropyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl]methyl]benzamide
-
-
4,6-diphenyl-N-hydroxypyridone
-
a lead compound for non-peptidic inhibitor screening against glyoxalase I
-
4-(biphenyl-4-yl)-1-hydroxy-6-phenylpyridin-2(1H)-one
-
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4-(but-1-yn-1-yl)-1-hydroxy-6-phenylpyridin-2(1H)-one
-
-
4-bromoacetoxy-1-(S-glutathionyl)-acetoxy butane
-
competitive inhibition of GLO1, the inhibitor is able to covalently bind to the free sulfhydryl group of Cys60 in the hydrophobic binding pocket adjacent to the enzyme active site and partially inactivate the enzyme, no complete inhibition, binding structure analysis, overview
-
4-butyl-1-hydroxy-6-phenylpyridin-2(1H)-one
-
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4-[(4E)-5-(3,4-dimethoxyphenyl)-2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-3-oxopenta-1,4-dien-1-yl]benzene-1,2-dicarbaldehyde
-
three-ring curcumin derivative, in binding model two rings lay in the opening of the active site, the third is buried into hydrophobic pocket site
6-(1-butyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-hydroxy-4-phenylpyridin-2(1H)-one
-
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adenine
-
-
adenosine
-
-
amino-group reagents
-
-
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aniline
-
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baicalein
Baicalin
-
30% inhibition of rhGLO I at 0.1 mM
benzimidazole <