Information on EC 3.1.2.4 - 3-hydroxyisobutyryl-CoA hydrolase

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

EC NUMBER
COMMENTARY hide
3.1.2.4
-
RECOMMENDED NAME
GeneOntology No.
3-hydroxyisobutyryl-CoA hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3-hydroxy-2-methylpropanoyl-CoA + H2O = CoA + 3-hydroxy-2-methylpropanoate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of thioester
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
alanine metabolism
-
-
beta-alanine biosynthesis II
-
-
beta-Alanine metabolism
-
-
L-valine degradation I
-
-
Metabolic pathways
-
-
Propanoate metabolism
-
-
propanoyl-CoA degradation II
-
-
valine metabolism
-
-
Valine, leucine and isoleucine degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
3-hydroxy-2-methylpropanoyl-CoA hydrolase
Also hydrolyses 3-hydroxypropanoyl-CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
9025-88-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain ATCC 14579
UniProt
Manually annotated by BRENDA team
beagle
-
-
Manually annotated by BRENDA team
strain UK-1
-
-
Manually annotated by BRENDA team
strain UK-1
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
-
a role for peroxisomal metabolism in cold stress signaling, and plant tolerance to cold stress and darkness-induced starvation. Is needed for fatty acid beta-oxidation and valine catabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-3-hydroxy-2-methylpropanoyl-CoA + H2O
CoA + (S)-3-hydroxy-2-methylpropanoate
show the reaction diagram
-
-
-
?
(S)-methylmalonyl-CoA + H2O
CoA + methylmalonate
show the reaction diagram
-
-
-
-
?
3-hydroxy-2-methylbutyryl-CoA + H2O
CoA + 3-hydroxy-2-methylbutyrate
show the reaction diagram
-
low activity
-
?
3-hydroxy-2-methylpropanoyl-CoA + H2O
3-hydroxy-2-methylpropanoate + CoA
show the reaction diagram
-
substrate is an intermediate in the pathway of valine catabolism, which is unique in that it produces a radily diffusible monocarboxylic acid
-
?
3-hydroxy-2-methylpropanoyl-CoA + H2O
?
show the reaction diagram
3-hydroxy-2-methylpropanoyl-CoA + H2O
CoA + 3-hydroxy-2-methylpropanoate
show the reaction diagram
3-hydroxy-3-phenylpropionyl-CoA + H2O
3-hydroxy-3-phenylpropionate + CoA
show the reaction diagram
-
-
-
?
3-hydroxyisobutyryl-CoA + H2O
CoA + 3-hydroxyisobutyrate
show the reaction diagram
-
formation of an anhydride reaction intermediate, Glu164 is involved
-
?
3-hydroxypropanoyl-CoA + H2O
CoA + 3-hydroxypropanoate
show the reaction diagram
cinnamoyl-CoA + H2O
cinnamic acid + CoA
show the reaction diagram
-
-
-
?
DL-3-hydroxybutyryl-CoA + H2O
CoA + DL-3-hydroxybutyrate
show the reaction diagram
-
low activity
-
?
L-3-hydroxybutyryl-CoA + H2O
CoA + L-3-hydroxybutyrate
show the reaction diagram
-
low activity
-
?
p-coumaroyl-CoA + H2O
p-coumaric acid + CoA
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
3-hydroxy-2-methylpropanoyl-CoA + H2O
3-hydroxy-2-methylpropanoate + CoA
show the reaction diagram
-
substrate is an intermediate in the pathway of valine catabolism, which is unique in that it produces a radily diffusible monocarboxylic acid
-
?
3-hydroxy-2-methylpropanoyl-CoA + H2O
?
show the reaction diagram
3-hydroxy-2-methylpropanoyl-CoA + H2O
CoA + 3-hydroxy-2-methylpropanoate
show the reaction diagram
3-hydroxypropanoyl-CoA + H2O
CoA + 3-hydroxypropanoate
show the reaction diagram
Q6NVY1
hydrolysis of beta-hydroxypropionyl-CoA, an intermediate in a minor pathway of propionate metabolism
-
-
-
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetoacetyl-CoA
acetyl-CoA
Cu2+
at 1 mM causes more than 90% inhibition of activity
DL-3-hydroxybutyryl-CoA
DL-methylmalonyl-CoA
isobutyryl-CoA
malonyl-CoA
n-valeryl-CoA
propionyl-CoA
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006
(S)-3-hydroxy-2-methylpropanoyl-CoA
0.025
3-hydroxypropionyl-CoA
0.0029
cinnamoyl-CoA
at 30C, in 50 mM Tris/HCl buffer, pH 7.0
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
150 - 266
3-hydroxy-2-methylpropanoyl-CoA
1 - 89
3-hydroxyisobutyryl-CoA
additional information
additional information
Pseudomonas aeruginosa
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.12
acetoacetyl-CoA
-
recombinant enzyme, pH 8.0, 30C
2.61
acetyl-CoA
-
recombinant enzyme, pH 8.0, 30C
0.14
DL-3-hydroxybutyryl-CoA
-
recombinant enzyme, pH 8.0, 30C
2.26
DL-methylmalonyl-CoA
-
recombinant enzyme, pH 8.0, 30C
1.19
isobutyryl-CoA
-
recombinant enzyme, pH 8.0, 30C
1.6
malonyl-CoA
-
recombinant enzyme, pH 8.0, 30C
0.72
n-valeryl-CoA
-
recombinant enzyme, pH 8.0, 30C
0.83
propionyl-CoA
-
recombinant enzyme, pH 8.0, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.073
recombinant BCH in Escherichia coli strain BL21(DE3) crude extract
244
-
purified recombinant enzyme, substrate 3-hydroxypropionyl-CoA
430
-
purified recombinant enzyme, substrate (S)-3-hydroxy-2-methylpropanoyl-CoA
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
-
hydrolysis of (S)-methylmalonyl-CoA
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 10.5
-
pH 5.0: about 40% of maximal activity, pH 10.5: about 80% of maximal activity, hydrolysis of 3-hydroxy-2-methylpropanoyl-CoA
5 - 7
-
pH 5.0, about 30% of maximal activity, pH 7.0: 65% of maximal activity, hydrolysis of (S)-methylmalonyl-CoA
5.1 - 10.3
-
at least
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
46% reduced activity compared to healthy cells
Manually annotated by BRENDA team
-
promyelocytic leukemia cell line
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by Ni chromatography
from rat liver, 7200fold, to homogeneity
-
native enzyme from mitochondrial membranes of HL-60 cells by two-step heparin affinity chromatography method using divalent cations, e.g. Mg2+, as eluents
-
recombinant enzyme from Escherichia coli, removal of His-tag with thrombin
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CHY1 cDNA cloned behind the 35S promoter in a binary vector, introduced into homozygous chy1-10 mutant plants by Agrobacterium tumefaciens strain GV3101 transformation
-
DNA and amino acid sequence determination and analysis, expression in Escherichia coli BL21(DE3) as His-tagged enzyme
-
expression in Escherichia coli
open-reading frame of the Chy1 gene amplified, cDNA ligated into the vector pEX5-CT/TOPO TA to create a fusion of the open-reading frame with a His tag-coding extension at the C-terminus. Plasmid transferred into Escherichia coli BL21 (DE3) cells for expression
subcloning in Escherichia coli strain XL1-Blue, and expression in Escherichia coli strain BL21 (DE3) under control of the T7 promoter, co-expression with the beta-ketothiolase gene from Ralstonia eutropha strain H16 and the (S)-3-hydroxybutyryl-CoA dehydrogenase gene from Ralstonia eutropha strain H16, or Clostridium acetobutylicum strain ATCC824 leads to biosynthesis of enantiomerically pure (S)-3-hydroxybutyric acid in the engineered Escherichia coli cells, extracellular product, method optimization, overview
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D151N
-
reduced activity
E143A
-
no detectable activity
E143D
-
no detectable activity
E143Q
-
no detectable activity
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