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Monocyclic monoterpene ketone monooxygenase

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Monocyclic monoterpene ketone monooxygenase
Identifiers
EC no.1.14.13.105
Databases
IntEnzIntEnz view
BRENDABRENDA entry
ExPASyNiceZyme view
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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 (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
(4a) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
(4b) 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one 3-isopropenyl-6-oxoheptanoate (spontaneous)

Monocyclic monoterpene ketone monooxygenase is a flavoprotein (FAD).

References

  1. ^ van der Werf, M.J.; Swarts, H.J.; de Bont, J.A. (1999). "Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene". Appl. Environ. Microbiol. 65 (5): 2092–2102. PMC 91303. PMID 10224006.
  2. ^ Van Der Werf, M.J. (2000). "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. doi:10.1042/0264-6021:3470693. PMC 1221005. PMID 10769172.
  3. ^ van der Werf, M.J.; Boot, A.M. (2000). "Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14". Microbiology. 146: 1129–1141. doi:10.1099/00221287-146-5-1129. PMID 10832640.{{cite journal}}: CS1 maint: unflagged free DOI (link)