Information on EC 1.14.13.69 - alkene monooxygenase

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

EC NUMBER
COMMENTARY hide
1.14.13.69
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RECOMMENDED NAME
GeneOntology No.
alkene monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
propene + NADH + H+ + O2 = 1,2-epoxypropane + NAD+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
epoxidation
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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
2-methylpropene degradation
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Chloroalkane and chloroalkene degradation
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ethene and chloroethene degradation
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isoprene degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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propene degradation
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SYSTEMATIC NAME
IUBMB Comments
alkene,NADH:oxygen oxidoreductase
This bacterial binuclear non-heme iron enzyme is a multicomponent enzyme complex comprising an oxygenase, a reductase, and a Rieske-type ferredoxin. The enzyme from the bacterium Xanthobacter sp. strain Py2 contains an additional small protein of unknown function that is essential for activity. In general, the enzyme oxygenates C2 to C6 aliphatic alkenes, although enzymes from different organisms show different substrate range. With propene as substrate, the stereospecifity of the epoxypropane formed is 95% (R) and 5% (S).
CAS REGISTRY NUMBER
COMMENTARY hide
63439-50-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
L1; multi-component enzyme
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Manually annotated by BRENDA team
E20
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Manually annotated by BRENDA team
P-IV-B-11 and P-V-B-171
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Manually annotated by BRENDA team
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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
(R)-styrene oxide + NADH + H+ + O2
?
show the reaction diagram
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?
(s)-styrene oxid + NADH + H+ + O2
?
show the reaction diagram
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?
2-cresol + NADH + H+ + O2
?
show the reaction diagram
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?
3-cresol + NADH + H+ + O2
?
show the reaction diagram
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?
4-cresol + NADH + H+ + O2
?
show the reaction diagram
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?
chloroethene + NADH + H+ + O2
2-chlorooxirane + NAD+ + H2O
show the reaction diagram
ethene + NADH + H+ + O2
?
show the reaction diagram
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?
propene + NADH + H+ + O2
1,2-epoxypropane + NAD+ + H2O
show the reaction diagram
propene + NADH + O2
1,2-epoxypropane + NAD+ + H2O
show the reaction diagram
toluene + NADH + H+ + O2
?
show the reaction diagram
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?
trans-1,2-dichloroethylene + NADH + H+ + O2
2,3-dichlorooxirane + NAD+ + H2O
show the reaction diagram
trichloroethylene + NADH + H+ + O2
2,2,3-trichlorooxirane + NAD+ + H2O
show the reaction diagram
vinyl chloride + NADH + H+ + O2
?
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
ethene + NADH + H+ + O2
?
show the reaction diagram
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?
propene + NADH + H+ + O2
1,2-epoxypropane + NAD+ + H2O
show the reaction diagram
propene + NADH + O2
1,2-epoxypropane + NAD+ + H2O
show the reaction diagram
vinyl chloride + NADH + H+ + O2
?
show the reaction diagram
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
the enzyme contains a Rieske-type ferredoxin. AMO requires a small catalytic coupling/effector protein, AamD, the coupling protein cannot or very poorly be substituted by coupling proteins of AMOs of other species, e.g. IsoD from Rhodococcus sp. strain AD45, or PmoB from Mycobacterium sp. strain M156, substitution with IsoD changes the regioselectivity of toluene hydroxylation and stereoselectivity of styrene epoxidation, although this is accompanied by a high level of uncoupling, overview
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
[2Fe-2S]cluster
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the reductase component contains two prosthetic groups, an FAD centre and a [2Fe-2S] cluster. The FAD moiety is reduced by bound NADH in a two-electron reaction. The electrons are then transported to the [2Fe-2S] centre one at a time, which reduces the di-iron centre of the epoxydase. Reduction of the di-iron centre is required for oxygen binding and substrate oxidation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
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2 mM, 40% inhibition. Activity is completely restored by 2 mM Fe2+
1,2-Epoxypropane
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8-hydroxyquinoline
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Acetylene
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Ethyne
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irreversible inhibition in the presence of NADH, suicide substrate, growth inhibition when added to the culture medium
propyne
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
AamD
the enzyme requires interaction with the small catalytic coupling/effector protein, substitution of AamD with IsoD, the coupling protein from the closely related isoprene monooxygenase, changes the regioselectivity of toluene hydroxylation and stereoselectivity of styrene epoxidation, although this is accompanied by a high level of uncoupling
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additional information
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epoxyethane, a metabolic intermediate of ethene biodegradation, induces enzyme expression, acetate reactivates extant AkMO in starved vinyl chloride- or ethene-grown cultures, overview
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.016 - 0.235
Propene
0.187
trichlorethene
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.145
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purified enzyme, pH 7.5, 30°C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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strain JS614 grows on the C2 alkenes ethene, vinyl chloride, and vinyl fluoride as sole carbon sources. The presence of 400-800 microM ethene oxide extended the growth substrate range to propene and butene. Propene-dependent growth of JS614 is CO2-dependent and is prevented by the carboxylase/reductase inhibitor 2-bromoethanesulfonic acid, while growth on ethene is not CO2-dependent or 2-bromoethanesulfonic acid-sensitive. Propene oxide at 0.05-0.1 mM exerts inhibitory effects on growth of JS614 on both acetate and ethene, and on ethene oxide-induced growth on ethene
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9650
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alpha2beta2gamma2, 2 * 58100, 2 * 38000, 2 * 9650, calculated from deduced amino acid sequences, masses in SDS-PAGE appear to be smaller (alpha and gamma subunits) or larger (beta subunit)
9740
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x * 58037, oxygenase alpha-subunit, + x * 9740, gamma-subunit, + x * 13359, ferredoxin, + x * 11193, coupling or effector protein, + 38188, oxygenase beta-subunit, + x * 34171, reductase subunit, calculation from nucleotide sequence
11193
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x * 58037, oxygenase alpha-subunit, + x * 9740, gamma-subunit, + x * 13359, ferredoxin, + x * 11193, coupling or effector protein, + 38188, oxygenase beta-subunit, + x * 34171, reductase subunit, calculation from nucleotide sequence
13359
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x * 58037, oxygenase alpha-subunit, + x * 9740, gamma-subunit, + x * 13359, ferredoxin, + x * 11193, coupling or effector protein, + 38188, oxygenase beta-subunit, + x * 34171, reductase subunit, calculation from nucleotide sequence
34171
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x * 58037, oxygenase alpha-subunit, + x * 9740, gamma-subunit, + x * 13359, ferredoxin, + x * 11193, coupling or effector protein, + 38188, oxygenase beta-subunit, + x * 34171, reductase subunit, calculation from nucleotide sequence
38000
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alpha2beta2gamma2, 2 * 58100, 2 * 38000, 2 * 9650, calculated from deduced amino acid sequences, masses in SDS-PAGE appear to be smaller (alpha and gamma subunits) or larger (beta subunit)
58000
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SDS-PAGE
58037
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x * 58037, oxygenase alpha-subunit, + x * 9740, gamma-subunit, + x * 13359, ferredoxin, + x * 11193, coupling or effector protein, + 38188, oxygenase beta-subunit, + x * 34171, reductase subunit, calculation from nucleotide sequence
58100
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alpha2beta2gamma2, 2 * 58100, 2 * 38000, 2 * 9650, calculated from deduced amino acid sequences, masses in SDS-PAGE appear to be smaller (alpha and gamma subunits) or larger (beta subunit)
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexamer
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alpha2beta2gamma2, 2 * 58100, 2 * 38000, 2 * 9650, calculated from deduced amino acid sequences, masses in SDS-PAGE appear to be smaller (alpha and gamma subunits) or larger (beta subunit)
additional information
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant proteins from Escherichia coli
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Xanthobacter autotrophicus
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expression of wild-type and mutant enzymes
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gene etnC, expression analysis under different culture conditions, overview
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native and His-tagged protein expressed in Escherichia coli Rosetta(DE3)(pLysS)
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
both propene and propene oxide induce expression of the gene encoding the alpha subunit of alkene monooxygenase, etnC, to a similar level as ethene and ethene oxide
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information