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Information on EC 1.14.13.105 - monocyclic monoterpene ketone monooxygenase
for references in articles please use BRENDA:EC1.14.13.105
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
1.14.13.105 monocyclic monoterpene ketone monooxygenase
IUBMB Comments
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 . 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 .
The expected taxonomic range for this enzyme is: Rhodococcus erythropolis
Reaction Schemes
showSynonyms
mmkmo, baeyer-villiger mono-oxygenase, nadph-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase, nadph-dependent dihydrocarvone monooxygenase, monocyclic monoterpene ketone mono-oxygenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Baeyer-Villiger mono-oxygenase
Baeyer-Villiger monooxygenase
BVMO
dihydrocarvone 1,2-monooxygenase
MMKMO
monocyclic monoterpene ketone mono-oxygenase
NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase
NADPH-dependent dihydrocarvone monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(-)-menthone + NADPH + H+ + O2 = (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O
-
-
-
-
(iso)-dihydrocarvone + NADPH + H+ + O2 = 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O
-
-
-
-
1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
followed by the spontaneous reaction of 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one = 3-isopropenyl-6-oxoheptanoate
-
-
-
dihydrocarvone + NADPH + H+ + O2 = 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
MetaCyc
(4R)-carveol and (4R)-dihydrocarveol degradation, (4S)-carveol and (4S)-dihydrocarveol degradation
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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].
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CAS REGISTRY NUMBER
COMMENTARY
288264-72-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1R)-pulegone + NADPH + H+ + O2
?
-
Substrates: 31% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1R,4R)-dihydrocarvone + NADPH + H+ + O2
(4R,7R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3S)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
(1R,4S)-menthone + NADPH + H+ + O2
(4R,7S)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
(1S)-pulegone + NADPH + H+ + O2
?
-
Substrates: 51% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3R)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
(1S,4R)-dihydrocarvone + NADPH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
(1S,4R)-menthone + NADPH + H+ + O2
(4S,7R)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: 82% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1S,4R)iso-dihydrocarvone + NADPH + H+ + O2
(3S,4R)-6-isopropenyl-3-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(4S)-carvone + NADPH + H+ + O2
?
-
Substrates: 14% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
1,2-cyclohexanedione + NADPH + H+ + O2
?
-
Substrates: 95% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
1,4-cyclohexanedione + NADPH + H+ + O2
?
-
Substrates: 92% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2,2-dimethylcyclohexanone + NADPH + H+ + O2
?
-
Substrates: 161% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2,6-dimethylcyclohexanone + NADPH + H+ + O2
?
-
Substrates: 108% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2-allylcyclohexanone + NADPH + H+ + O2
?
-
Substrates: 145% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2-chlorocyclohexanone + NADPH + H+ + O2
?
-
Substrates: 112% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2-methoxycyclohexanone + NADPH + H+ + O2
?
-
Substrates: 168% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2-methylcyclohexanone + NADPH + H+ + O2
?
-
Substrates: 155% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
2-phenylcyclohexanone + NADPH + O2
?
-
Substrates: 148% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
3-methylcyclohexanone + NADPH + H+ + O2
?
-
Substrates: 151% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
4-methylcyclohexanone + NADPH + H+ + O2
?
-
Substrates: 40% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
8-mercaptomenthone + NADPH + H+ + O2
?
-
Substrates: 14% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
cycloheptanone + NADPH + H+ + O2
?
-
Substrates: 10% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
cyclohexanone + NADPH + H+ + O2
?
-
Substrates: 151% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
cyclopentanone + NADPH + H+ + O2
?
-
Substrates: 12% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
norcamphor + NADPH + H+ + O2
?
-
Substrates: 145% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1R,4R)-dihydrocarvone + NADPH + H+ + O2
(4R,7R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(1R,4R)-dihydrocarvone + NADPH + H+ + O2
(4R,7R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3S)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3S)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: 3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 133% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: 3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 133% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1R,4S)-menthone + NADPH + H+ + O2
(4R,7S)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: 76% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1R,4S)-menthone + NADPH + H+ + O2
(4R,7S)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: 76% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3R)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
(3R)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: 3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 88% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2
3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
-
Substrates: 3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 88% of the activity with (1R,4R)-dihydrocarvone
Products: -
Products: -
?
dihydrocarvone + NADPH + O2
4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: no activity with NADH
Products: -
Products: -
?
dihydrocarvone + NADPH + O2
4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
-
Substrates: no activity with NADH
Products: -
Products: -
?
additional information
?
-
-
Substrates: NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase is involved in the limonene degradation pathway
Products: -
Products: -
?
additional information
?
-
-
Substrates: MMKMO is involved in the conversion of the monocyclic monoterpene ketone intermediates formed in the degradation pathways of all stereoisomers of three different monocyclic monoterpenes, i.e. limonene, (dihydro)carveol and menthol. MMKMO converts all enantiomers of the natural substrates with almost equal efficiency
Products: -
Products: -
?
additional information
?
-
-
Substrates: MMKMO converts all enantiomers of the natural substrates with almost equal efficiency. No activity with NADH
Products: -
Products: -
?
additional information
?
-
-
Substrates: NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase is involved in the limonene degradation pathway
Products: -
Products: -
?
additional information
?
-
-
Substrates: MMKMO is involved in the conversion of the monocyclic monoterpene ketone intermediates formed in the degradation pathways of all stereoisomers of three different monocyclic monoterpenes, i.e. limonene, (dihydro)carveol and menthol. MMKMO converts all enantiomers of the natural substrates with almost equal efficiency
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
Substrates: NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase is involved in the limonene degradation pathway
Products: -
Products: -
?
additional information
?
-
-
Substrates: MMKMO is involved in the conversion of the monocyclic monoterpene ketone intermediates formed in the degradation pathways of all stereoisomers of three different monocyclic monoterpenes, i.e. limonene, (dihydro)carveol and menthol. MMKMO converts all enantiomers of the natural substrates with almost equal efficiency
Products: -
Products: -
?
additional information
?
-
-
Substrates: NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase is involved in the limonene degradation pathway
Products: -
Products: -
?
additional information
?
-
-
Substrates: MMKMO is involved in the conversion of the monocyclic monoterpene ketone intermediates formed in the degradation pathways of all stereoisomers of three different monocyclic monoterpenes, i.e. limonene, (dihydro)carveol and menthol. MMKMO converts all enantiomers of the natural substrates with almost equal efficiency
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no inhibition with 1 mM iodoacetate, iodoacetamide, EDTA, 2,2'-dipyridyl and DTT
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.13
(1S,4R)-1-hydroxy-2-oxolimonene
-
30°C and glyine/NaOH buffer, pH 9.5
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4.9
(1R,4S)-1-hydroxy-2-oxolimonene
-
30°C and glyine/NaOH buffer, pH 9.5
3.9
(1S,4R)-1-hydroxy-2-oxolimonene
-
30°C and glyine/NaOH buffer, pH 9.5
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
10
-
4 min, inactivation of MMKMO in glycine/NaOH buffer is observed above pH 8.5
8.5
-
4 min, inactivation of MMKMO in Tris/HCl buffer is observed above pH 8.5
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
van der Werf, M.J.; Swarts, H.J.; de Bont, J.A.
Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene
Appl. Environ. Microbiol.
65
2092-2102
1999
Rhodococcus erythropolis, Rhodococcus erythropolis DCL14
brenda
van der Werf, M.J.
Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways
Biochem. J.
347 Pt 3
693-701
2000
Rhodococcus erythropolis, Rhodococcus erythropolis DCL14
brenda
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