Monocyclic monoterpene ketone monooxygenase

Monocyclic monoterpene ketone monooxygenase
Identifiers
EC number 1.14.13.105
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum

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 91303Freely accessible. 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 1221005Freely accessible. 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.
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