Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy

(-)-menthone,NADPH:oxygen oxidoreductase

(1) (-)-menthone + NADPH + H+ + O2 = (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O [RN:R08925];
(2) dihydrocarvone + NADPH + H+ + O2 = 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O [RN:R06386];
(3) (iso)-dihydrocarvone + NADPH + H+ + O2 = 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O [RN:R06388 R06389];
(4a) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O [RN:R06400 R09390];
(4b) 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one = 3-isopropenyl-6-oxoheptanoate (spontaneous) [RN:R09391 R09392]

R06386 R06388 R06389 R06400 R08925 R09390 R09391 R09392;
(other) R06387
Reaction

(-)-menthone [CPD:C00843];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
dihydrocarvone [CPD:C18018];
(iso)-dihydrocarvone;
1-hydroxymenth-8-en-2-one [CPD:C18019];
7-hydroxy-4-isopropenyl-7-methyloxepan-2-one

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].

EC 1.14.13.105 created 2008

1  [PMID:10224006]

2  [PMID:10769172]

3  [PMID:10832640]

C00843 + C00005 + C00080 + C00007 <=> C18027 + C00006 + C00001

Baeyer-Villiger monooxygenase

1.14.13.105