Information on EC 1.3.1.85 - crotonyl-CoA carboxylase/reductase

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

EC NUMBER
COMMENTARY hide
1.3.1.85
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RECOMMENDED NAME
GeneOntology No.
crotonyl-CoA carboxylase/reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2S)-ethylmalonyl-CoA + NADP+ = (E)-but-2-enoyl-CoA + CO2 + NADPH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
carboxylation
reductive carboxylation
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
crotonyl-CoA/ethylmalonyl-CoA/hydroxybutyryl-CoA cycle (engineered)
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ethylmalonyl-CoA pathway
Glyoxylate and dicarboxylate metabolism
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
(2S)-ethylmalonyl-CoA:NADP+ oxidoreductase (decarboxylating)
The reaction is catalysed in the reverse direction. This enzyme, isolated from the bacterium Rhodobacter sphaeroides, catalyses (E)-but-2-enoyl-CoA-dependent oxidation of NADPH in the presence of CO2. When CO2 is absent, the enzyme catalyses the reduction of (E)-but-2-enoyl-CoA to butanoyl-CoA, but with only 10% of maximal activity (relative to (E)-but-2-enoyl-CoA carboxylation).
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Methylobacterium extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
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Manually annotated by BRENDA team
variant 108
UniProt
Manually annotated by BRENDA team
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M1SQA1
UniProt
Manually annotated by BRENDA team
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M1SQA1
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
B8XVS5;
crotonyl-CoA carboxylase/reductase, a key enzyme of the ethylmalonyl-CoA pathway for acetyl-CoA assimilation, is not essential for growth with 3-hydroxypropionate
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E)-3-cyclohexylprop-2-enoyl-CoA + NADPH + CO2 + H+
(2S)-2-carboxy-3-cyclohexylpropanoyl-CoA + NADP+
show the reaction diagram
(2E)-4-methylhex-2-enoyl-CoA + NADPH + CO2 + H+
[(2R)-2-methylbutyl]propanedioyl-CoA + NADP+
show the reaction diagram
(2E)-5-chloropent-2-enoyl-CoA + NADPH + CO2 + H+
(2S)-2-carboxy-5-chloropentanoyl-CoA + NADP+
show the reaction diagram
(2E)-5-methylhex-2-enoyl-CoA + NADPH + CO2 + H+
(2S)-(3-methylbutyl)propanedioyl-CoA + NADP+
show the reaction diagram
(2E)-6-methyloct-2-enoyl-CoA + NADPH + CO2 + H+
(2S)-2-carboxy-6-methyloctanoyl-CoA + NADP+
show the reaction diagram
M1SQA1;
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-
?
(2E)-hept-2-en-6-ynoyl-CoA + NADPH + CO2 + H+
(2S)-2-craboxy-hept-6-ynoyl-CoA + NADP+
show the reaction diagram
M1SQA1;
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-
-
?
(2E)-hex-2-enoyl-CoA + NADPH + CO2 + H+
(S)-2-butylpropanedioyl-CoA + NADP+
show the reaction diagram
M1SQA1;
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-
-
?
(2E)-oct-2-enoyl-CoA + NADPH + CO2 + H+
(2S)-2-carboxyoctanoyl-CoA + NADP+
show the reaction diagram
(E)-crotonyl-CoA + CO2 + NADPH + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
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100% relative specific activity, the carboxylation reaction is the physiologically relevant reaction
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r
(E)-crotonyl-CoA + NADPH + H+
butyryl-CoA + NADP+
show the reaction diagram
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10% of maximal activity (compared with vmax of crotonyl-CoA carboxylation)
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?
3-indolylacryloyl-CoA + NADPH + CO2 + H+
indolylmethylmalonyl-CoA + NADP+
show the reaction diagram
4-coumaroyl-CoA + NADPH + CO2 + H+
(2S)2-carboxy-3-(4-hydroxyphenyl)propionyl-CoA + NADP+
show the reaction diagram
acryloyl-CoA + CO2 + NADPH + H+
methylmalonyl-CoA + NADP+
show the reaction diagram
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acryloyl-CoA is accepted as an alternative substrate analogue by the enzyme with 40% relative activity (compared with vmax of crotonyl-CoA carboxylation)
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?
cinnamoyl-CoA + NADPH + CO2 + H+
(2S)2-carboxy-3-phenylpropionyl-CoA + NADP+
show the reaction diagram
crotonyl-CoA + CO2 + NADPH + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
crotonyl-CoA + CO2 + NADPH + H+
?
show the reaction diagram
crotonyl-CoA + NADPH + CO2 + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
crotonyl-CoA + NADPH + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
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?
crotonyl-CoA + NADPH + H+
?
show the reaction diagram
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?
crotonyl-CoA + NADPH + H+
butyryl-CoA + NADP+
show the reaction diagram
decanoyl-CoA + NADPH + H+
?
show the reaction diagram
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?
hexanoyl-CoA + NADPH + H+
?
show the reaction diagram
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?
octanoyl-CoA + NADPH + H+
?
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
(E)-crotonyl-CoA + CO2 + NADPH + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
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100% relative specific activity, the carboxylation reaction is the physiologically relevant reaction
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r
crotonyl-CoA + CO2 + NADPH + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
crotonyl-CoA + CO2 + NADPH + H+
?
show the reaction diagram
crotonyl-CoA + NADPH + H+
(2S)-ethylmalonyl-CoA + NADP+
show the reaction diagram
Q6T2B7
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?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetate
B8XVS5;
activity is upregulated during photoheterotrophic growth on acetate compared to the activities during growth on succinate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2
(2S)-ethylmalonyl-CoA
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in 100 mM Tris-HCl buffer (pH 7.9), temperature not specified in the publication
0.2 - 0.4
(E)-crotonyl-CoA
0.14 - 0.2
4-Coumaroyl-CoA
0.5
acryloyl-CoA
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pH and temperature not specified in the publication
0.089 - 0.38
cinnamoyl-CoA
0.2
CO2
0.4 - 1.58
crotonyl-CoA
0.7
NADPH
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
104
(2S)-ethylmalonyl-CoA
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in 100 mM Tris-HCl buffer (pH 7.9), temperature not specified in the publication
0.0735 - 0.109
4-Coumaroyl-CoA
0.0688 - 0.0877
cinnamoyl-CoA
0.0675 - 0.1755
crotonyl-CoA
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
520
(2S)-ethylmalonyl-CoA
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in 100 mM Tris-HCl buffer (pH 7.9), temperature not specified in the publication
0.525 - 0.545
4-Coumaroyl-CoA
0.18 - 0.985
cinnamoyl-CoA
0.0583 - 0.257
crotonyl-CoA
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
47700
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2 * 47700, gel filtration
105000
143000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
homotetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor diffusion method, using 100 mM CAPS-NaOH pH 10.0, 38% (v/v) PEG 400
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE-Sepharose column chromatography and Cibacron Blue 3GA agarose column chromatography
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Ni-NTA column chromatography and Superdex 200HR gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli BLR(DE3) cells
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expressed in Escherichia coli JM101 cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
although the reaction is reversible, the activity of crotonyl-CoA carboxylase/reductase is up-regulated at least 60fold for Rhodobacter sphaeroides during growth with acetate versus succinate
TetR-type activator CcrR regulates the expression of crotonyl-CoA reductase/carboxylase. A ccrR null mutant strain ismpaired in its ability to grow on C1 and C2 compounds, correlating with the reduced activity of crotonyl-CoA reductase/carboxylase. The activity of the promoter required for ccr expression decreases as much as 50% in the absence of ccrR compared to wild-type. CcrR directly binds to the region upstream of the katA-ccr promoter
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A182G
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inactive
A182L
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the mutant with increased activity selectively catalyzes carboxylation over the regular reduction reaction
V350A
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the mutant shows increased activity compared to the wild type enzyme
V350F
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the mutant shows increased activity compared to the wild type enzyme
V350G
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the mutant shows increased activity compared to the wild type enzyme
A182G
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inactive
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A182L
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the mutant with increased activity selectively catalyzes carboxylation over the regular reduction reaction
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V350A
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the mutant shows increased activity compared to the wild type enzyme
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V350F
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the mutant shows increased activity compared to the wild type enzyme
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V350G
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the mutant shows increased activity compared to the wild type enzyme
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