Information on EC 1.3.1.8 - acyl-CoA dehydrogenase (NADP+)

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

EC NUMBER
COMMENTARY hide
1.3.1.8
-
RECOMMENDED NAME
GeneOntology No.
acyl-CoA dehydrogenase (NADP+)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acyl-CoA + NADP+ = 2,3-dehydroacyl-CoA + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dehydrogenation
-
-
-
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oxidation
-
-
-
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redox reaction
-
-
-
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reduction
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Fatty acid elongation
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-
Metabolic pathways
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-
SYSTEMATIC NAME
IUBMB Comments
acyl-CoA:NADP+ 2-oxidoreductase
The liver enzyme acts on enoyl-CoA derivatives of carbon chain length 4 to 16, with optimum activity on 2-hexenoyl-CoA. In Escherichia coli, cis-specific and trans-specific enzymes exist [EC 1.3.1.37 cis-2-enoyl-CoA reductase (NADPH) and EC 1.3.1.38 trans-2-enoyl-CoA reductase (NADPH)].
CAS REGISTRY NUMBER
COMMENTARY hide
37251-07-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
3 different enzyme isoforms I, II and III, not exactly differentiated concerning elongation system I and II
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-
Manually annotated by BRENDA team
wild-type and neurological er mouse mutant
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
strain 2.4.1 (DSMZ 158)
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-
Manually annotated by BRENDA team
gene ccr, enzyme CCR
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-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E)-hexadec-2-enoyl-CoA + NADPH
palmitoyl-CoA + NADP+
show the reaction diagram
-
-
-
-
?
2-cis-octenoyl-CoA + NADPH
octanoyl-CoA + NADP+
show the reaction diagram
2-methyl-trans-crotonyl-CoA + NADPH
2-methylbutanoyl-CoA + NADP+
show the reaction diagram
-
2% of trans-crotonyl-CoA activity
-
-
?
2-trans,4-trans-decadienoyl-CoA + NADPH
?
show the reaction diagram
-
low activity
-
-
?
2-trans,4-trans-hexadienoyl-CoA + NADPH
?
show the reaction diagram
-
low activity
-
-
?
2-trans-8,11-eicosatrienoyl-CoA + NADPH
8,11-eicosadienoyl-CoA + NADP+
show the reaction diagram
-
fat-free dietary elevates the activity
-
?
2-trans-decenoyl-CoA + NAD(P)H
decanoyl-CoA + NADP+
show the reaction diagram
2-trans-dodecenoyl-CoA + NAD(P)H
dodecanoyl-CoA + NAD(P)+
show the reaction diagram
2-trans-hexadecenoyl-CoA + NADPH
hexadecanoyl CoA + NADP+
show the reaction diagram
2-trans-hexenoyl-CoA + NAD(P)H
hexanoyl-CoA + NADP+
show the reaction diagram
2-trans-octadecenoyl-CoA + NAD(P)H
octadecanoyl-CoA + NAD(P)+
show the reaction diagram
2-trans-octenoyl-CoA + NAD(P)H
octanoyl-CoA + NADP+
show the reaction diagram
2-trans-octenoyl-CoA + NADPH
octanoyl-CoA + NADP+
show the reaction diagram
-
-
-
-
?
2-trans-tetradecenoyl-CoA + NADPH
tetradecanoyl-CoA + NADP+
show the reaction diagram
3-butenoyl-CoA + NADPH
butanoyl-CoA + NADP+
show the reaction diagram
-
7% of trans-crotonyl-CoA activity
-
-
?
3-methyl-crotonyl-CoA + NADPH
3-methylbutanoyl-CoA + NADP+
show the reaction diagram
-
17% of trans-crotonyl-CoA activity
-
-
?
5-hydroxyundec-cis-2-enoyl-CoA + NADPH
5-hydroxyundecanoyl-CoA + NADP+
show the reaction diagram
-
-
-
-
?
6,9-octadecadienoyl-CoA + NADPH
?
show the reaction diagram
-
fat-free dietary elevates the activity
-
-
?
crotonyl-CoA + NAD(P)H
butanoyl-CoA + NADP+
show the reaction diagram
crotonyl-CoA + NADPH
butanoyl-CoA + NADP+
show the reaction diagram
-
-
-
-
-
crotonyl-CoA + NADPH
butyryl-CoA + NADP+
show the reaction diagram
-
-
-
-
-
crotonyl-CoA + reduced acceptor
butyryl-CoA + oxidized acceptor
show the reaction diagram
primary fluorescent chlorophyll catabolite + NADP+
red chlorophyll catabolite + NADPH + H+
show the reaction diagram
trans-2-eicosenoyl-CoA + NADPH
eicosanoyl-CoA + NADP+
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
(2E)-hexadec-2-enoyl-CoA + NADPH
palmitoyl-CoA + NADP+
show the reaction diagram
-
-
-
-
?
5-hydroxyundec-cis-2-enoyl-CoA + NADPH
5-hydroxyundecanoyl-CoA + NADP+
show the reaction diagram
-
-
-
-
?
crotonyl-CoA + reduced acceptor
butyryl-CoA + oxidized acceptor
show the reaction diagram
-
enzyme is involved in synthesizing methylmalonyl-CoA precursors for monensin biosynthesis, pathway flux, overview
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-
?
primary fluorescent chlorophyll catabolite + NADP+
red chlorophyll catabolite + NADPH + H+
show the reaction diagram
-
stereospecific reaction. RCCR catalyzes the ferredoxin-dependent and site-specific reduction of the C20/C1 double bond of red chlorophyll catabolite, RCC, the catabolic intermediate produced in chlorophyll degradation
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-
r
trans-2-eicosenoyl-CoA + NADPH
eicosanoyl-CoA + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FMN
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1 mol per mol of protein, prosthetic group is essentiell for the reaction
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-decynoyl-CoA
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2-methylcrotonyl-CoA
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CoA-activated enzyme, competitive inhibition
2-trans-octadecenoyl-CoA
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without bovine serum albumin substrate-induced inhibition at 0.02-0.03 mM
3-methylcrotonyl-CoA
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-
4-Chloro-7-nitrobenzo-2-oxa-1,3-diazole
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5,5'-dithiobis(2-nitrobenzoate)
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-
acetyl-CoA
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competitive
Butyryl-CoA
coenzyme A
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in free form inhibits fatty acid sythesis
diethyldicarbonate
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dithiothreitol
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above 10 mM
ebselen
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i.e. 2-phenylisoselenazol-3-one
iodoacetamide
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Isonicotinamide
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-
malonyl-CoA
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non-competitive
methylmalonyl-CoA
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i.e. tiglyl-CoA
monoiodoacetate
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-
N-ethylmaleimide
NADH
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in presence of NADPH 0.1 mM
NADPH
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concentration above 0.1 mM
p-chloromercuribenzoate
palmitoyl-CoA
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without bovine serum albumin substrate-induced inhibition at 0.02-0.03 mM
pyridoxal 5'-phosphate
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competitive with NADPH, 80% inactivation at 1 mM, reversibel
trans-2-hexenoyl-CoA
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competitive inhibition of crotonoyl-CoA reduction, but not of 2-trans-hexadecenoyl-CoA and 2-trans-decenoyl-CoA reduction
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
coenzyme A
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free form, strong activator of the reduction
dithiothreitol
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enhancement in the range of 5-10 mM
additional information
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bovine serum albumin in assay mixture elevated the activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0011 - 1.2
2-cis-Octenoyl-CoA
0.083
2-Eicosenoyl-CoA
-
-
0.0011 - 0.1
2-trans-hexadecenoyl-CoA
0.0005
2-trans-hexenoyl-CoA
0.01 - 0.016
2-trans-octenoyl-CoA
0.0025 - 0.003
5-Hydroxyundec-cis-2-enoyl-CoA
0.13
acetyl-CoA
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-
0.0067
Butyryl-CoA
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-
0.02
crotonyl-CoA
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-
0.01 - 0.045
NADPH
0.0033
trans-crotonyl-CoA
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-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0029
2-methylcrotonyl-CoA
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-
0.006
acetyl-CoA
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-
0.005
Butyryl-CoA
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0.021
malonyl-CoA
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00065
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11 to 26 days after birth of wild-type mice
0.00081
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mouse mutant, activity is independent on developmental stage
0.00267
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activity peak 17 days after birth of mutant mice
0.0117
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purified enzyme, substrate 2-trans,4-trans-hexadienoyl-CoA
0.0143
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mitochondrial fraction
0.0219
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purified enzyme, substrate 2-trans,4-trans-decadienoyl-CoA
0.29
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purified enzyme, substrate 2-trans-tetradecenoyl-CoA
1.42
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purified enzyme, substrate 2-trans-decenoyl-CoA
1.46
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purified enzyme, substrate 2-trans-octenoyl-CoA
1.54
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partially purified
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8.5
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depending on substrate and type of reductase
7.2 - 8.5
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8
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above pH 8.0, effect of CoA on pH-profile
8.3
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in HEPES and Bicine buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8.3
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with CoA changed from sigmoidal curve to flat one
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 42
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-
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000 - 60000
-
gel filtration
36270
calculated from sequence
59000
-
gel filtration
68000
-
sucrose density gradient centrifugation
85000
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reductase type II, gel filtration
98000
-
gradient, native PAGE
180000
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reductase type I, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
? * 32000, SDS-PAGE, monomer or dimer
dimer
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2 * 35000, SDS-PAGE, with assumed MW of about 70000
additional information
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RCCR folds into a characteristic alpha/beta/alpha sandwich, similar to that observed in the ferredoxin-dependent bilin reductase family, structure comparisosns, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified recombinant red chlorophyll catabolite-bound RCCRDELTA49, and red chlorophyll catabolite-bound or substrate-free F218V RCCRDELTA49, sitting drop vapor diffusion method, 20°C, protein solution is mixed with an equal volume of reservoir solution and equilibrated against reservoir solution containing 30% w/v PEG 2000 monomethyl ether, 0.1 M ammonium acetate, 3% v/v dioxane, and 0.1 M 4-morpholineethanesulfonic acid–NaOH, pH 6.5, 1 day, X-ray diffraction structure determination and analysis at 2.0-2.6 A resolution
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
-
reductase type I: 30 min, 50% loss of activity, reductase type II: no activity with 5 hydroxyundec-cis-2-enoyl-CoA, up to 80% activity with cis or trans-oct-2-enoyl-CoA
60
-
reductase type I: 3 min, 80% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
fatty acid synthetase with enoyl-CoA reductase activity: denaturation by mechanical agitation, exposure to air, uneven surfaces such as scratched glass, membranes for ultrafiltration
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
denaturation by exposure to air
-
390851
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-15°C, sucrose solution, loss of 15-20% activity overnight
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2-3°C, absence of dithiothreitol, half life 3 h
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liquid N2, 30-50% loss of activity by thawing
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
as part of fatty acid synthase
-
DEAE-Sepharose column chromatography and Cibacron Blue column chromatography
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fatty acid synthetase, also exhibiting crotonyl-CoA reductase activity
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recombinant GST-tagged wild-type and F218V mutant RCCR lacking the chloroplast transit peptide, Met1 to Gln39, i.e. RCCRDELTA49
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reductase type I and II
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expression in Streptomyces cinnamonensis strains C730.1 and L1
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expression of GST-tagged wild-type and F218V mutant RCCR lacking the chloroplast transit peptide, Met1 to Gln39
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F218V
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a mutant protein that produces the stereoisomer of primary fluorescent chlorophyll catabolites at the C1 position, the F218V mutation changes the stereospecificity in RCCR. Construction of wild-type and F218V mutant RCCR lacking the chloroplast transit peptide, Met1 to Gln39, i.e. RCCRDELTA49
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
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optimization of oil-based extended fermentation of recombinant Streptomyces cinnamonensis, expressing the enzyme from Streptomyces collinus, is used to provide methylmalonyl-CoA precursors for monensin biosynthesis, overview
synthesis
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oil-based extended fermentation of recombinant Streptomyces cinnamonensis, expressing the enzyme from Streptomyces collinus, is used to provide methylmalonyl-CoA precursors for monensin biosynthesis