Information on EC 1.1.1.86 - ketol-acid reductoisomerase (NADP+)

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

EC NUMBER
COMMENTARY hide
1.1.1.86
-
RECOMMENDED NAME
GeneOntology No.
ketol-acid reductoisomerase (NADP+)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2R)-2,3-dihydroxy-3-methylbutanoate + NADP+ = (2S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
rearrangement
-
-
-
-
redox reaction
-
-
-
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reduction
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
isoleucine metabolism
-
-
valine metabolism
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-
Valine, leucine and isoleucine biosynthesis
-
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Pantothenate and CoA biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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Biosynthesis of antibiotics
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pyruvate fermentation to isobutanol (engineered)
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L-valine biosynthesis
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L-isoleucine biosynthesis III
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L-isoleucine biosynthesis I (from threonine)
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-
SYSTEMATIC NAME
IUBMB Comments
(R)-2,3-dihydroxy-3-methylbutanoate:NADP+ oxidoreductase (isomerizing)
Also catalyses the reduction of 2-ethyl-2-hydroxy-3-oxobutanoate to 2,3-dihydroxy-3-methylpentanoate. The enzyme, found in many bacteria and archaea, is specific for NADPH (cf. EC 1.1.1.382, ketol-acid reductoisomerase (NAD+) and EC 1.1.1.383, ketol-acid reductoisomerase [NAD(P)+]).
CAS REGISTRY NUMBER
COMMENTARY hide
9075-02-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SwissProt
Manually annotated by BRENDA team
a histatin-resistant derivative of Candida albicans strain 132A is used
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-
Manually annotated by BRENDA team
Digitaria adscendens
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
morning glory
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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
gene Pi-kari1
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
black nightshade
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R)-2,3-dihydroxy-3-methylbutanoate + NADP+
(2S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
show the reaction diagram
(R)-2,3-dihydroxy-3-methylbutanoate + NADP+
(S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH
show the reaction diagram
-
the enzyme is involved in biosynthesis of the branched chain amino acids valine and leucine, pathway overview
-
-
?
(R)-2,3-dihydroxy-3-methylbutanoate + NADP+
(S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
show the reaction diagram
(S)-2-acetolactate + NADH + H+
(R)-2,3-dihydroxyisovalerate + NAD+
show the reaction diagram
(S)-2-acetolactate + NADH + H+
2,3-dihydroxy-3-methylbutanoate + NAD+
show the reaction diagram
(S)-2-acetolactate + NADPH + H+
(R)-2,3-dihydroxyisovalerate + NADP+
show the reaction diagram
(S)-2-acetolactate + NADPH + H+
2,3-dihydroxy-3-methylbutanoate + NADP+
show the reaction diagram
2-aceto-2-hydroxybutyrate + NADP+
(2R,3R)-2,3-dihydroxy-3-methylvalerate + NADPH + H+
show the reaction diagram
-
-
-
-
r
2-aceto-2-hydroxybutyrate + NADPH
2,3-dihydroxy-3-methylvalerate + NADP+
show the reaction diagram
2-aceto-2-hydroxybutyrate + NADPH + H+
? + NADP+
show the reaction diagram
2-acetolactate + NADP+
(2R)-2,3-dihydroxy-3-isovalerate + NADPH + H+
show the reaction diagram
-
-
-
-
r
2-acetolactate + NADPH
2,3-dihydroxy-3-methylbutanoate + NADP+
show the reaction diagram
2-acetolactate + NADPH
2,3-dihydroxy-3-methylbutanoate + NADP+ + H+
show the reaction diagram
-
the enzyme is the second of the valine pathway
-
-
r
2-acetolactate + NADPH
2,3-dihydroxyisovalerate + NADP+
show the reaction diagram
2-acetolactate + NADPH + H+
2,3-dihydroxy-3-methylbutanoate + NADP+
show the reaction diagram
2-acetolactate + NADPH + H+
3-hydroxy-2-ketobutyrate + NADP+
show the reaction diagram
-
-
-
-
r
2-hydroxy-2-ethyl-3-oxobutanoate + NADPH + H+
2,3-dihydroxy-2-ethyl-butanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-hydroxy-2-ethyl-3-oxobutanoate + NADPH + H+
2,3-dihydroxy-2-ethylbutanoate + NADP+
show the reaction diagram
2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
2,3-dihydroxy-2-methyl-butanoate + NADP+
show the reaction diagram
-
-
-
-
?
2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
2,3-dihydroxy-2-methylbutanoate + NADP+
show the reaction diagram
2-ketobutyrate + NADPH + H+
?
show the reaction diagram
-
-
-
-
r
2-ketoisovalerate + NADPH + H+
?
show the reaction diagram
-
-
-
-
r
2-ketopantoate + NADPH + H+
?
show the reaction diagram
-
-
-
-
r
2-ketovalerate + NADPH + H+
?
show the reaction diagram
-
-
-
-
r
2-methylacetoacetate + NADPH + H+
3-hydroxy-2-methylbutanoate + NADP+
show the reaction diagram
2-methylacetoacetate + NADPH + H+
3-hydroxy-2-methylbutanoate+ NADP+
show the reaction diagram
-
-
-
-
?
3-hydroxy-3-ethyl-2-oxobutanoate + NADPH + H+
2,3-dihydroxy-3-ethyl-butanoate + NADP+
show the reaction diagram
-
-
-
-
?
3-hydroxy-3-ethyl-2-oxobutanoate + NADPH + H+
2,3-dihydroxy-3-ethylbutanoate + NADP+
show the reaction diagram
3-hydroxy-3-methyl-2-ketobutyrate + NADP+
?
show the reaction diagram
-
-
-
-
r
3-hydroxy-3-methyl-2-oxobutanoate + NADPH + H+
2,3-dihydroxy-3-methyl-butanoate + NADP+
show the reaction diagram
-
-
-
-
?
3-hydroxy-3-methyl-2-oxobutanoate + NADPH + H+
2,3-dihydroxy-3-methylbutanoate + NADP+
show the reaction diagram
3-hydroxypyruvate + NADPH + H+
?
show the reaction diagram
3-hydroxypyruvate + NADPH + H+
? + NADP+
show the reaction diagram
acetolactate + NADPH + H+
2,3-dihydroxy-2-methylbutanoate + NADP+
show the reaction diagram
hydroxypyruvate + NADPH
glycerate + NADP+
show the reaction diagram
-
-
-
?
hydroxypyruvate + NADPH + H+
2,3-dihydroxypropanoate + NADP+
show the reaction diagram
hydroxypyruvate + NADPH + H+
2,3-dihydroxypropanoate+ NADP+
show the reaction diagram
-
-
-
-
?
NADP+ + 3-hydroxy-3-methyl-2-oxobutanoate
NADPH + acetolactate
show the reaction diagram
-
-
-
?
NADPH + 2-aceto-2-hydroxybutyrate
NADP+ + ?
show the reaction diagram
NADPH + 2-acetolactate
NADP+ + 3-hydroxy-3-methyl-2-oxobutyrate
show the reaction diagram
NADPH + 2-oxo-3-hydroxyisovalerate
NADP+ + alpha,beta-dihydroxyisovalerate
show the reaction diagram
-
-
-
?
NADPH + alpha-aceto-alpha-hydroxybutyrate
NADP+ + ?
show the reaction diagram
-
enzyme of isoleucine biosynthesis
-
-
?
pyrroline-5-carboxylate + NADPH + H+
? + NADP+
show the reaction diagram
pyruvate + NADPH + H+
2-hydroxypropanoate + NADP+
show the reaction diagram
pyruvate + NADPH + H+
?
show the reaction diagram
-
-
-
-
r
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
(2R)-2,3-dihydroxy-3-methylbutanoate + NADP+
(2S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
show the reaction diagram
(R)-2,3-dihydroxy-3-methylbutanoate + NADP+
(S)-2-hydroxy-2-methyl-3-oxobutanoate + NADPH + H+
show the reaction diagram
-
-
-
-
r
(S)-2-acetolactate + NADH + H+
(R)-2,3-dihydroxyisovalerate + NAD+
show the reaction diagram
(S)-2-acetolactate + NADPH + H+
(R)-2,3-dihydroxyisovalerate + NADP+
show the reaction diagram
2-aceto-2-hydroxybutyrate + NADPH
2,3-dihydroxy-3-methylvalerate + NADP+
show the reaction diagram
-
-
-
-
?
2-aceto-2-hydroxybutyrate + NADPH + H+
? + NADP+
show the reaction diagram
2-acetolactate + NADPH
2,3-dihydroxy-3-methylbutanoate + NADP+
show the reaction diagram
2-acetolactate + NADPH
2,3-dihydroxy-3-methylbutanoate + NADP+ + H+
show the reaction diagram
-
the enzyme is the second of the valine pathway
-
-
r
2-acetolactate + NADPH
2,3-dihydroxyisovalerate + NADP+
show the reaction diagram
-
-
-
-
?
NADPH + alpha-aceto-alpha-hydroxybutyrate
NADP+ + ?
show the reaction diagram
-
enzyme of isoleucine biosynthesis
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
the reaction requires a divalent metal ion
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,1-cyclopropanedicarboxylic acid
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i.e. CPCA, inhibition in vivo, effect on pea root length, shoot length, and fermentative metabolism, effects of KARI inhibition effects on other enzymes, such as alcohol dehydrogenase, EC 1.1.1.1, pyruvate dehydrogenase, EC 4.1.1.1, lactate dehydrogenase, EC 1.1.1.27, and alanine aminotransferase, EC 2.6.1.2, overview
1-aminocarbonyl-cyclopropane carboxylate
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1-aminocarbonylcyclopropanecarboxylate
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1-carbamoylcyclopropanecarboxylic acid
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1-cyano-cyclopropane carboxylate
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1-cyano-N-(2,4,5-trichlorophenyl)cyclopropanecarboxamide
-
inhibition rate: 0%
1-cyano-N-(2,4-dichlorophenyl)cyclopropanecarboxamide
-
inhibition rate: 97.04%
1-cyano-N-(2-hydroxyethyl)cyclopropanecarboxamide
-
inhibition rate: 98.92%
1-cyano-N-(2-methylphenyl)cyclopropanecarboxamide
-
inhibition rate: 100%
1-cyano-N-(4-methoxyphenyl)cyclopropanecarboxamide
-
inhibition rate: 3.95%
1-cyano-N-(4-methylphenyl)cyclopropanecarboxamide
-
inhibition rate: 61.21%
1-cyano-N-phenylcyclopropanecarboxamide
-
inhibition rate: 77.23%
1-cyano-N-[(E)-(3,3-dichloroprop-1-yn-1-yl)diazenyl]sulfanylcyclopropanecarboxamide
-
inhibition rate: 100%
1-cyano-N-[2-(trifluoromethyl)phenyl]cyclopropanecarboxamide
-
inhibition rate: 0%
1-cyano-N-[3-(trifluoromethyl)phenyl]cyclopropanecarboxamide
-
inhibition rate: 0%
1-cyano-N-[4-(trifluoromethyl)phenyl]cyclopropanecarboxamide
-
inhibition rate: 0%
1-cyano-N-[[(3-methylcyclopropa-1,2-dien-1-yl)amino]sulfanyl]cyclopropanecarboxamide
-
inhibition rate: 69.81%
1-cyanocyclopropanecarboxylate
-
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1-cyanocyclopropanecarboxylic acid
1-hydroxycyclopropanecarboxylate
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11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11-one
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2,3-dihydroxy-3-isovalerate
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2,3-dihydroxy-3-methylbutanoic acid
-
linear noncompetitive inhibitor of both 2-acetolactate and NADPH
2,3-dihydroxy-3-methylbutyrate
-
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2-(4-benzylpiperazin-1-yl)-N-(3,4-dichlorophenyl)acetamide
2-(4-benzylpiperazin-1-yl)-N-arylacetamide
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2-(4-methoxybenzamido)benzoic acid
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2-dimethylphosphinoyl-2-hydroxyacetate
2-dimethylphosphinoyl-2-hydroxyacetic acid
2-hydroxy-2-methyl-3-oxopentanoate
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2-Hydroxy-2-methylbutyrate
-
0.01 M 45% inhibition
2-Hydroxybutyrate
-
0.01 M, 48% inhibition
2-Hydroxyisovalerate
2-Methyllactate
2-Oxo-3-hydroxyisovalerate
-
0.001 mM, 58% inhibition
2-oxoisovalerate
-
0.01 M, 21% inhibition
2-[2-(4-morpholino)]acetamido-4-methylthiazole
-
-
2-[[(4-methoxyphenyl)carbonyl]amino]benzoic acid
3-aminopyridine-NADP+
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-
3-hydroxy-2-oxobutanoic acid
3-hydroxy-3-methyl-2-oxobutanoic acid
4,4'-(pentamethylenedioxy)dibenzamidne bis(2-hydroxyethanesulfonate)
4-(2,4-dichlorophenoxy)benzenecarboximidamide
-
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4-(2-fluorophenoxy)benzenecarboximidamide
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4-(3-chlorophenoxy)benzenecarboximidamide
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4-(4-chlorophenoxy)benzenecarboximidamide
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4-phenoxybenzenecarboximidamide
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arsenite
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slight inhibition
ascorbic acid
-
slight inhibition with 2-acetolactate as substrate
chlorsulfuron
cyclopropane-1,1-dicarboxylate
cyclopropane-1,1-dicarboxylic acid
-
-
dimethylmalonate
-
slow-binding inhibitor
ethyl 1-cyanocyclopropanecarboxylate
-
inhibition rate: 0%
ethyl 3-hydroxy-2-oxobutanoate
ethyl 3-methyl-3-hydroxy-2-oxobutanoate
ethyl [(2-chlorophenyl)(hydroxy)amino](oxo)acetate
-
-
ethyl [hydroxy(2-methylphenyl)amino](oxo)acetate
-
-
ethyl [hydroxy(4-methylphenyl)amino](oxo)acetate
-
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ethyl [[4-(cyanomethyl)phenyl](hydroxy)amino](oxo)acetate
-
-
ethylene glycol
-
exhibits competitive and uncompetitive inhibition
HOE 704
IpOHA
L-ascorbic acid
-
slightly inhibitory with alpha-acetolactate as substrate
methyl [hydroxy(1-methylethyl)amino](oxo)acetate
-
-
metsulfuron-methyl
Mn2+
-
with acetolactate as substrate, Mn2+ behaves as a competitive inhibitor in presence of Mg2+
N'-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(2-fluorophenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(2-methyl-phenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(3-methyl-phenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(3-pyridinyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-butyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-ethyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-furan-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-heptyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-iso-propyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-isopropyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-methyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
-
N'-(5-octyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-pentyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-phenyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N'-(5-propyl-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea
-
-
N-(2-(piperidin-1-yl)ethyl)phthalimide
-
-
N-(3-bromophenyl)-1-cyanocyclopropanecarboxamide
-
inhibition rate: 17.25%
N-(3-chlorophenyl)-1-cyanocyclopropanecarboxamide
-
inhibition rate: 0%
N-(4-bromophenyl)-1-cyanocyclopropanecarboxamide
-
inhibition rate: 32.23%
N-(4-chlorophenyl)-1-cyanocyclopropanecarboxamide
-
inhibition rate: 93.92%
N-(5-substituted-1,3,4-thiadiazol-2-yl)-N-cyclopropylformyl-thiourea
-
-
N-Hydroxy-N-isopropyloxamate
NADP+
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbic acid
-
5 mM, enhances activity 2-hydroxy-2-ethyl-3-oxobutanoate as substrate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04 - 0.24
(S)-2-acetolactate
0.01
2-aceto-2-hydroxybutanoate
-
pH 8.2, 30C, chimeric enzyme Aabidopsis thaliana acetohydroxy acid synthase genetically fused in frame with the nucleotide sequence coding for the Spinacia oleracea acetohydroxy acid isomeroreductase and expressed in E. coli
0.002 - 0.78
2-aceto-2-hydroxybutyrate
0.01 - 5.5
2-acetolactate
0.3 - 75
2-hydroxy-2-ethyl-3-oxobutanoate
0.28 - 12
2-Hydroxy-2-methyl-3-oxobutanoate
4.56
2-Ketobutyrate
-
pH 8.0, 37C, wild-type enzyme
6.91
2-ketoisovalerate
-
pH 8.0, 37C, wild-type enzyme
0.17
2-ketopantoate
-
pH 8.0, 37C, wild-type enzyme
3.15
2-Ketovalerate
-
pH 8.0, 37C, wild-type enzyme
30 - 60
2-Methylacetoacetate
0.21
3-hydroxy-2-ketobutyrate
-
pH 8.0, 37C, wild-type enzyme
0.29 - 50
3-hydroxy-3-ethyl-2-oxobutanoate
-
0.27
3-hydroxy-3-methyl-2-ketobutyrate
-
pH 8.0, 37C, wild-type enzyme
0.26 - 13
3-Hydroxy-3-methyl-2-oxobutanoate
0.334 - 15.3
3-hydroxypyruvate
0.893 - 60
Hydroxypyruvate
0.019 - 0.207
NADH
0.0089 - 0.072
NADP+
0.00016 - 11.2
NADPH
1.54 - 1200
pyruvate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.77 - 3.81
(S)-2-acetolactate
0.00417
2,3-Dihydroxy-3-methylbutanoate
-
pH 7.4, 25C
1.2 - 18.3
2-acetolactate
0.12 - 3.6
2-hydroxy-2-ethyl-3-oxobutanoate
0.24 - 3.6
2-Hydroxy-2-methyl-3-oxobutanoate
0.167
2-Ketobutyrate
-
pH 8.0, 37C
0.182
2-ketoisovalerate
-
pH 8.0, 37C
0.194
2-ketopantoate
-
pH 8.0, 37C
0.05
2-Ketovalerate
-
pH 8.0, 37C
0.4 - 2
2-Methylacetoacetate
0.594
3-hydroxy-2-ketobutyrate
-
pH 8.0, 37C
0.18 - 3.8
3-hydroxy-3-ethyl-2-oxobutanoate
-
3.511
3-hydroxy-3-methyl-2-ketobutyrate
-
pH 8.0, 37C
0.3 - 5.2
3-Hydroxy-3-methyl-2-oxobutanoate
4.5 - 26
3-hydroxypyruvate
0.5 - 2
Hydroxypyruvate
0.00183 - 0.3
NADH
0.00015 - 0.000667
NADP+
0.0000933 - 0.98
NADPH
0.021 - 8.6
pyruvate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.6 - 34.1
(S)-2-acetolactate
2.4 - 120
2-acetolactate
0.012 - 11.67
2-hydroxy-2-ethyl-3-oxobutanoate
0.02 - 7.14
2-Hydroxy-2-methyl-3-oxobutanoate
0.01 - 0.06
2-Methylacetoacetate
0.01 - 13.1
3-hydroxy-3-ethyl-2-oxobutanoate
-
0.03 - 11.92
3-Hydroxy-3-methyl-2-oxobutanoate
3.3 - 4.16
3-hydroxypyruvate
0.02 - 0.06
Hydroxypyruvate
0.0046 - 9
NADH
0.01 - 54.5
NADPH
0.0024 - 0.0061
pyrroline-5-carboxylate
0.001 - 0.008
pyruvate