Information on EC 1.14.13.105 - monocyclic monoterpene ketone monooxygenase:
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The lowest common taxonomy group for this enzyme is: Rhodococcus erythropolis

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EC NUMBERCOMMENTARY
1.14.13.105-

RECOMMENDED NAMEGeneOntology No.
monocyclic monoterpene ketone monooxygenase-

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.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---
dihydrocarvone + NADPH + H+ + O2 = 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram		----

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

PATHWAYKEGG LinkMetaCyc Link
(4R)-carveol and (4R)-dihydrocarveol degradation-PWY-5922
(4S)-carveol and (4S)-dihydrocarveol degradation-PWY-5927
limonene degradation I (D-limonene)-PWY-5923
limonene degradation II (L-limonene)-PWY-5924

SYSTEMATIC NAMEIUBMB Comments
(-)-menthone,NADPH:oxygen oxidoreductaseA 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].

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
Baeyer-Villiger mono-oxygenaseRhodococcus erythropolis--684953
Baeyer-Villiger monooxygenaseRhodococcus erythropolis--684540
BVMORhodococcus erythropolis--684953
dihydrocarvone 1,2-monooxygenaseRhodococcus erythropolis--684540
MMKMORhodococcus erythropolis--684953
monocyclic monoterpene ketone mono-oxygenaseRhodococcus erythropolis--684953
NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenaseRhodococcus erythropolis--684540
NADPH-dependent dihydrocarvone monooxygenaseRhodococcus erythropolis--684540

CAS REGISTRY NUMBERCOMMENTARY
288264-72-2-

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Rhodococcus erythropolisstrain DCL14684540, 684953--Manually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
(1R)-pulegone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-31% of the activity with (1R,4R)-dihydrocarvone684953--?
(1R,4R)-dihydrocarvone + NADPH + H+ + O2(4R,7R)-4-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis--684953--?
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2(3S)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis--684540--?
(1R,4S)-1-hydroxy-2-oxolimonene + NADPH + H+ + O23-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis-3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 133% of the activity with (1R,4R)-dihydrocarvone684953--?
(1R,4S)-menthone + NADPH + H+ + O2(4R,7S)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis-76% of the activity with (1R,4R)-dihydrocarvone684953--?
(1S)-pulegone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-51% of the activity with (1R,4R)-dihydrocarvone684953--?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O2(3R)-3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis--684540--?
(1S,4R)-1-hydroxy-2-oxolimonene + NADPH + H+ + O23-isopropenyl-6-oxoheptanoate + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis-3-isopropenyl-6-oxoheptanoate is the spontaneous rearrangement product of the lactone formed by MMKMO. 88% of the activity with (1R,4R)-dihydrocarvone684953--?
(1S,4R)-menthone + NADPH + H+ + O2(4S,7R)-7-isopropyl-4-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis-82% of the activity with (1R,4R)-dihydrocarvone684953--?
(1S,4R)iso-dihydrocarvone + NADPH + H+ + O2(3S,4R)-6-isopropenyl-3-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis--684953--?
(4S)-carvone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-14% of the activity with (1R,4R)-dihydrocarvone684953--?
(4S,4R)-dihydrocarvone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis--684953--?
1,2-cyclohexanedione + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-95% of the activity with (1R,4R)-dihydrocarvone684953--?
1,4-cyclohexanedione + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-92% of the activity with (1R,4R)-dihydrocarvone684953--?
2,2-dimethylcyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-161% of the activity with (1R,4R)-dihydrocarvone684953--?
2,6-dimethylcyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-108% of the activity with (1R,4R)-dihydrocarvone684953--?
2-allylcyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-145% of the activity with (1R,4R)-dihydrocarvone684953--?
2-chlorocyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-112% of the activity with (1R,4R)-dihydrocarvone684953--?
2-methoxycyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-168% of the activity with (1R,4R)-dihydrocarvone684953--?
2-methylcyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-155% of the activity with (1R,4R)-dihydrocarvone684953--?
2-phenylcyclohexanone + NADPH + O2?
show the reaction diagram		Rhodococcus erythropolis-148% of the activity with (1R,4R)-dihydrocarvone684953--?
3-methylcyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-151% of the activity with (1R,4R)-dihydrocarvone684953--?
4-methylcyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-40% of the activity with (1R,4R)-dihydrocarvone684953--?
8-mercaptomenthone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-14% of the activity with (1R,4R)-dihydrocarvone684953--?
cycloheptanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-10% of the activity with (1R,4R)-dihydrocarvone684953--?
cyclohexanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-151% of the activity with (1R,4R)-dihydrocarvone684953--?
cyclopentanone + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-12% of the activity with (1R,4R)-dihydrocarvone684953--?
norcamphor + NADPH + H+ + O2?
show the reaction diagram		Rhodococcus erythropolis-145% of the activity with (1R,4R)-dihydrocarvone684953--?
dihydrocarvone + NADPH + O24-isopropenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O
show the reaction diagram		Rhodococcus erythropolis-no activity with NADH684540--?
additional information?-Rhodococcus erythropolis-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 efficiency684953---
additional information?-Rhodococcus erythropolis-NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase is involved in the limonene degradation pathway684540---
additional information?-Rhodococcus erythropolis-MMKMO converts all enantiomers of the natural substrates with almost equal efficiency. No activity with NADH684953---

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
additional information?-Rhodococcus erythropolis-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 efficiency684953--
additional information?-Rhodococcus erythropolis-NADPH-dependent 1-hydroxy-2-oxolimonene 1,2-monooxygenase is involved in the limonene degradation pathway684540--

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
FADRhodococcus erythropolis-contains 1 mol FAD per monomer as prosthetic group684953 2D-image
NADPHRhodococcus erythropolis-no activity with NADH684953 2D-image

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
No entries in this field

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
ATPRhodococcus erythropolis--684953 2D-image
p-chloromercuriobenzoateRhodococcus erythropolis-0.1 mM, 14% inhibition684953 2D-image
phenylhydrazineRhodococcus erythropolis-1 mM, 10% inhibition684953 2D-image
SDSRhodococcus erythropolis-1 mM, 97% inhibition684953 2D-image
ZnCl2Rhodococcus erythropolis-1 mM 33% inhibition684953 2D-image
HgCl2Rhodococcus erythropolis-1 mM, 85% inhibition684953 2D-image
additional informationRhodococcus erythropolis-no inhibition with 1 mM iodoacetate, iodoacetamide, EDTA, 2,2'-dipyridyl and DTT684953-

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
0.12-(1R,4S)-menthoneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
0.13-(1S,4R)-1-hydroxy-2-oxolimoneneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
0.13-(4R)-dihydrocarvoneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
0.038-NADPHRhodococcus erythropolis--684953 2D-image

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
4.9-(1R,4S)-1-hydroxy-2-oxolimoneneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
3.6-(1R,4S)-menthoneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
3.9-(1S,4R)-1-hydroxy-2-oxolimoneneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
6-(1S,4R)-menthoneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image
3.9-(4R)-dihydrocarvoneRhodococcus erythropolis-30°C and glyine/NaOH buffer, pH 9.5684953 2D-image

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
9.5-ATPRhodococcus erythropolis--684953 2D-image

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
8-Rhodococcus erythropolis--684540
8.3-Rhodococcus erythropolis-pH-optimum in Tris/HCl buffer684953
9.5-Rhodococcus erythropolis-pH-optimum in glycine/NaOH buffer684953

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
36-Rhodococcus erythropolis--684953

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
culture condition:(4R)-limonene-grown cellRhodococcus erythropolis--684540Manually annotated by BRENDA team

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
No entries in this field

PDBSCOPCATHORGANISM
No entries in this field

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
57000-Rhodococcus erythropolis-gel filtration684953

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
monomerRhodococcus erythropolis-1 * 60000, SDS-PAGE684953

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
8.5-Rhodococcus erythropolis-4 min, inactivation of MMKMO in Tris/HCl buffer is observed above pH 8.5684953
10-Rhodococcus erythropolis-4 min, inactivation of MMKMO in glycine/NaOH buffer is observed above pH 8.5684953

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
40-Rhodococcus erythropolis-inactivation above684953

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-Rhodococcus erythropolis-684953

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
684540van der Werf, M.J.; Swarts, H.J.; de Bont, J.A.Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limoneneAppl. Environ. Microbiol.652092-21021999Rhodococcus erythropolis PubMed
684953van der Werf, M.J.Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathwaysBiochem. J.347 Pt 3693-7012000Rhodococcus erythropolis PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.105)
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MetaCyc
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)