IntEnz

EC 1.14.13.105 - Monocyclic monoterpene ketone monooxygenase

IntEnz Enzyme Nomenclature
EC 1.14.13.105

Names

Reactions

• (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
• (4) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 3-isopropenyl-6-oxoheptanoate + NADP+ + H2O
• (5) (4a) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O
• (6) (4b) 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one = 3-isopropenyl-6-oxoheptanoate (spontaneous)

Cofactor

• FAD

Comments:

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].

Links to other databases

References

1. van der Werf, M.J., Swarts, H.J. and de Bont, J.A.M.
   Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene.
   Appl. Environ. Microbiol. 65 : 2092-2102 (1999). [PMID: 10224006]
2. Van Der Werf, M.J.
   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 (2000). [PMID: 10769172]
3. van der Werf, M.J. and Boot, A.M.
   Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14.
   Microbiology 146 : 1129-1141 (2000). [PMID: 10832640]

[EC 1.14.13.105 created 2008]