Biology:Monocyclic monoterpene ketone monooxygenase

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Short description: Class of enzymes

Monocyclic monoterpene ketone monooxygenase (EC 1.14.13.105, 1-hydroxy-2-oxolimonene 1,2-monooxygenase, dihydrocarvone 1,2-monooxygenase, MMKMO) is an enzyme with systematic name (-)-menthone,NADPH:oxygen oxidoreductase.[1][2][3] This enzyme catalyses the following chemical reaction

(1) (-)-menthone + NADPH + H+ + O2 [math]\displaystyle{ \rightleftharpoons }[/math] (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O
(2) dihydrocarvone + NADPH + H+ + O2 [math]\displaystyle{ \rightleftharpoons }[/math] 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
(3) (iso)-dihydrocarvone + NADPH + H+ + O2 [math]\displaystyle{ \rightleftharpoons }[/math] 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O
(4a) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 [math]\displaystyle{ \rightleftharpoons }[/math] 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
(4b) 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one [math]\displaystyle{ \rightleftharpoons }[/math] 3-isopropenyl-6-oxoheptanoate (spontaneous)

Monocyclic monoterpene ketone monooxygenase is a flavoprotein (FAD).

References

  1. "Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene". Applied and Environmental Microbiology 65 (5): 2092–102. May 1999. PMID 10224006. 
  2. "Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways". The Biochemical Journal 347 Pt 3: 693–701. May 2000. doi:10.1042/0264-6021:3470693. PMID 10769172. 
  3. "Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14". Microbiology 146 ( Pt 5): 1129–41. May 2000. doi:10.1099/00221287-146-5-1129. PMID 10832640. 

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