KEGG   ENZYME: 1.14.13.105
Entry
EC 1.14.13.105              Enzyme                                 
Name
monocyclic monoterpene ketone monooxygenase;
1-hydroxy-2-oxolimonene 1,2-monooxygenase;
dihydrocarvone 1,2-monooxygenase;
MMKMO
Class
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
Sysname
(-)-menthone,NADPH:oxygen oxidoreductase
Reaction(IUBMB)
(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]
Reaction(KEGG)
R06386 R06388 R06389 R06400 R08925 R09390 R09391 R09392;
(other) R06387
Substrate
(-)-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
Product
(4R,7S)-7-isopropyl-4-methyloxepan-2-one [CPD:C18027];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
4-isopropenyl-7-methyloxepan-2-one [CPD:C11414];
6-isopropenyl-3-methyloxepan-2-one;
7-hydroxy-4-isopropenyl-7-methyloxepan-2-one;
3-isopropenyl-6-oxoheptanoate (spontaneous)
Comment
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].
History
EC 1.14.13.105 created 2008
Pathway
ec00902  Monoterpenoid biosynthesis
ec00903  Limonene degradation
ec01110  Biosynthesis of secondary metabolites
ec01120  Microbial metabolism in diverse environments
Reference
1  [PMID:10224006]
  Authors
van der Werf MJ, Swarts HJ, de Bont JA
  Title
Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene.
  Journal
Appl Environ Microbiol 65:2092-102 (1999)
DOI:10.1128/AEM.65.5.2092-2102.1999
Reference
2  [PMID:10769172]
  Authors
Van Der Werf MJ.
  Title
Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways.
  Journal
Biochem J 347 Pt 3:693-701 (2000)
DOI:10.1042/0264-6021:3470693
Reference
3  [PMID:10832640]
  Authors
van der Werf MJ, Boot AM
  Title
Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14.
  Journal
Microbiology 146 ( Pt 5):1129-41 (2000)
DOI:10.1099/00221287-146-5-1129
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.105
IUBMB Enzyme Nomenclature: 1.14.13.105
ExPASy - ENZYME nomenclature database: 1.14.13.105
BRENDA, the Enzyme Database: 1.14.13.105

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Pathway (8)   
   KEGG PATHWAY (8)   
Chemical substance (21)   
   KEGG COMPOUND (21)   
Chemical reaction (14)   
   KEGG REACTION (9)   
   KEGG RCLASS (5)   
Protein sequence (2)   
   UniProt (1)   
   SWISS-PROT (1)   
All databases (45)   

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