Information on EC 1.14.13.105 - monocyclic monoterpene ketone monooxygenase

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The expected taxonomic range for this enzyme is: Rhodococcus erythropolis

EC NUMBER
COMMENTARY hide
1.14.13.105
-
RECOMMENDED NAME
GeneOntology No.
monocyclic monoterpene ketone monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(-)-menthone + NADPH + H+ + O2 = (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
(iso)-dihydrocarvone + NADPH + H+ + O2 = 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
followed by the spontaneous reaction of 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one = 3-isopropenyl-6-oxoheptanoate
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-
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dihydrocarvone + NADPH + H+ + O2 = 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(4R)-carveol and (4R)-dihydrocarveol degradation
-
-
(4S)-carveol and (4S)-dihydrocarveol degradation
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Biosynthesis of secondary metabolites
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Limonene and pinene degradation
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Monoterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(-)-menthone,NADPH:oxygen oxidoreductase
A flavoprotein (FAD). This Baeyer-Villiger monooxygenase enzyme from the Gram-positive bacterium Rhodococcus erythropolis DCL14 has wide substrate specificity, catalysing the lactonization of a large number of monocyclic monoterpene ketones and substituted cyclohexanones [2]. Both (1R,4S)- and (1S,4R)-1-hydroxymenth-8-en-2-one are metabolized, with the lactone product spontaneously rearranging to form 3-isopropenyl-6-oxoheptanoate [1].
CAS REGISTRY NUMBER
COMMENTARY hide
288264-72-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain DCL14
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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
(1R)-pulegone + NADPH + H+ + O2
?
show the reaction diagram
(1R,4R)-dihydrocarvone + NADPH + H+ + O2
(4R,7R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3S)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram
(1R,4S)-menthone + NADPH + H+ + O2
(4R,7S)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram
-
76% of the activity with (1R,4R)-dihydrocarvone
-
-
?
(1S)-pulegone + NADPH + H+ + O2
?
show the reaction diagram
-
51% of the activity with (1R,4R)-dihydrocarvone
-
-
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3R)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram
-
3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 88% of the activity with (1R,4R)-dihydrocarvone
-
-
?
(1S,4R)-dihydrocarvone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
(1S,4R)-menthone + NADPH + H+ + O2
(4S,7R)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram
-
82% of the activity with (1R,4R)-dihydrocarvone
-
-
?
(1S,4R)iso-dihydrocarvone + NADPH + H+ + O2
(3S,4R)-6-isopropenyl-3-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(4S)-carvone + NADPH + H+ + O2
?
show the reaction diagram
-
14% of the activity with (1R,4R)-dihydrocarvone
-
-
?
1,2-cyclohexanedione + NADPH + H+ + O2
?
show the reaction diagram
-
95% of the activity with (1R,4R)-dihydrocarvone
-
-
?
1,4-cyclohexanedione + NADPH + H+ + O2
?
show the reaction diagram
-
92% of the activity with (1R,4R)-dihydrocarvone
-
-
?
2,2-dimethylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
161% of the activity with (1R,4R)-dihydrocarvone
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-
?
2,6-dimethylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
108% of the activity with (1R,4R)-dihydrocarvone
-
-
?
2-allylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
145% of the activity with (1R,4R)-dihydrocarvone
-
-
?
2-chlorocyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
112% of the activity with (1R,4R)-dihydrocarvone
-
-
?
2-methoxycyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
168% of the activity with (1R,4R)-dihydrocarvone
-
-
?
2-methylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
155% of the activity with (1R,4R)-dihydrocarvone
-
-
?
2-phenylcyclohexanone + NADPH + O2
?
show the reaction diagram
-
148% of the activity with (1R,4R)-dihydrocarvone
-
-
?
3-methylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
151% of the activity with (1R,4R)-dihydrocarvone
-
-
?
4-methylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
40% of the activity with (1R,4R)-dihydrocarvone
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-
?
8-mercaptomenthone + NADPH + H+ + O2
?
show the reaction diagram
-
14% of the activity with (1R,4R)-dihydrocarvone
-
-
?
cycloheptanone + NADPH + H+ + O2
?
show the reaction diagram
-
10% of the activity with (1R,4R)-dihydrocarvone
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-
?
cyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
151% of the activity with (1R,4R)-dihydrocarvone
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-
?
cyclopentanone + NADPH + H+ + O2
?
show the reaction diagram
-
12% of the activity with (1R,4R)-dihydrocarvone
-
-
?
dihydrocarvone + NADPH + O2
4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram
-
no activity with NADH
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-
?
norcamphor + NADPH + H+ + O2
?
show the reaction diagram
-
145% of the activity with (1R,4R)-dihydrocarvone
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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
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
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contains 1 mol FAD per monomer as prosthetic group
NADPH
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no activity with NADH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
HgCl2
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1 mM, 85% inhibition
p-chloromercuriobenzoate
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0.1 mM, 14% inhibition
phenylhydrazine
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1 mM, 10% inhibition
SDS
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1 mM, 97% inhibition
ZnCl2
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1 mM 33% inhibition
additional information
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no inhibition with 1 mM iodoacetate, iodoacetamide, EDTA, 2,2'-dipyridyl and DTT
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.12
(1R,4S)-menthone
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30C and glyine/NaOH buffer, pH 9.5
0.13
(1S,4R)-1-hydroxy-2-oxolimonene
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30C and glyine/NaOH buffer, pH 9.5
0.13
(4R)-dihydrocarvone
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30C and glyine/NaOH buffer, pH 9.5
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.9
(1R,4S)-1-hydroxy-2-oxolimonene
Rhodococcus erythropolis
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30C and glyine/NaOH buffer, pH 9.5
3.6
(1R,4S)-menthone
Rhodococcus erythropolis
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30C and glyine/NaOH buffer, pH 9.5
3.9
(1S,4R)-1-hydroxy-2-oxolimonene
Rhodococcus erythropolis
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30C and glyine/NaOH buffer, pH 9.5
6
(1S,4R)-menthone
Rhodococcus erythropolis
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30C and glyine/NaOH buffer, pH 9.5
3.9
(4R)-dihydrocarvone
Rhodococcus erythropolis
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30C and glyine/NaOH buffer, pH 9.5
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.3
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pH-optimum in Tris/HCl buffer
9.5
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pH-optimum in glycine/NaOH buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57000
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gel filtration
60000
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1 * 60000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5
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4 min, inactivation of MMKMO in Tris/HCl buffer is observed above pH 8.5
684953
10
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4 min, inactivation of MMKMO in glycine/NaOH buffer is observed above pH 8.5
684953
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
inactivation above
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE