EC 1 - Oxidoreductases
EC 1.14 - Acting on paired donors, with incorporation or reduction of molecular oxygen. The oxygen incorporated need not be derived from O2
EC 1.14.13 - With NADH or NADPH as one donor, and incorporation of one atom of oxygen
EC 1.14.13.105 - Monocyclic monoterpene ketone monooxygenase
IntEnz view
ENZYME view
IntEnz Enzyme Nomenclature
EC 1.14.13.105
Names
Accepted name:
monocyclic monoterpene ketone monooxygenase
Other
names:
1-hydroxy-2-oxolimonene 1,2-monooxygenase
dihydrocarvone 1,2-monooxygenase
MMKMO
dihydrocarvone 1,2-monooxygenase
MMKMO
Systematic name:
(−)-menthone,NADPH:oxygen oxidoreductase
Reactions
- (1) ()-menthone + NADPH + H+ + O2 = (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O
- (2) dihydrocarvone + NADPH + H+ + O2 = 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
- (3) (iso)-dihydrocarvone + NADPH + H+ + O2 = 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O
- (4) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
- (5) (4a) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
- (6) (4b) 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one = 3-isopropenyl-6-oxoheptanoate (spontaneous)
Cofactor
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 [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].
Links to other databases
UniProtKB/Swiss-Prot:
MMKMO_RHOER
References
-
Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene.Appl. Environ. Microbiol. 65 : 2092-2102 (1999). [PMID: 10224006]
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Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways.Biochem. J. 347 : 693-701 (2000). [PMID: 10769172]
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Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14.Microbiology 146 : 1129-1141 (2000). [PMID: 10832640]
[EC 1.14.13.105 created 2008]