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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
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MetaCyc Enzyme: monocyclic monoterpene ketone monooxygenase

Species: Rhodococcus erythropolis DCL14

Summary:
monocyclic monoterpene ketone monooxygenase is a Baeyer-Villiger mono-oxygenase that catalyzes the NADPH- and oxygen-dependent oxidation of the monocyclic monoterpene ketones 1-hydroxy-2-oxolimonene, dihydrocarvone and menthone.

The enzyme was purified to homogeneity from Rhodococcus erythropolis DCL14 [Van00]. It is a monomeric enzyme of 60 kDa and contains 1 mol of FAD/monomer as the prosthetic group. The enzyme has a broad substrate specificity, catalyzing the lactonization of a large number of monocyclic monoterpene ketones and substituted cyclohexanones. In addition, it converts all enantiomers of the natural substrates, although with different efficiencies. It plays an important role in the degradation of limonene, (dihydro)carveol and menthol [Van00].

Molecular Weight of Polypeptide: 60.0 kD (experimental) [Van00 ]

Gene-Reaction Schematic: ?

Instance reactions of [a menthone + NADPH + H+ + oxygen → a 7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O] (1.14.13.105):
i6: (+)-menthone + NADPH + H+ + oxygen → (4S,7R)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (1.14.13.105)

i7: (-)-menthone + NADPH + H+ + oxygen → (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (1.14.13.105)

Instance reactions of [a dihydrocarvone + NADPH + H+ + oxygen → a 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O] (1.14.13.105):
i3: (+)-dihydrocarvone + NADPH + H+ + oxygen → (4R,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O (1.14.13.105)

i4: (-)-isodihydrocarvone + NADPH + H+ + oxygen → (4S,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O (1.14.13.105)

Instance reaction of [an isodihydrocarvone + NADPH + H+ + oxygen → a 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O] (1.14.13.105):
i5: (+)-isodihydrocarvone + NADPH + oxygen + H+ → (3S,6R)-6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O (1.14.13.105)

Instance reactions of [a 1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen → a 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O] (no EC#):
i1: (1R,4S)-1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen → (4R)-7-hydroxy-4-isoprenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O (no EC#)

i2: (1S,4R)-1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen → (4S)-7-hydroxy-4-isoprenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O (no EC#)

Credits:
Created 12-May-2008 by Caspi R , SRI International


Enzymatic reaction of: 1-hydroxy-2-oxolimonene monooxygenase (monocyclic monoterpene ketone monooxygenase)

a 1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen <=> a 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is physiologically favored in the direction shown.

In Pathways: limonene degradation II (L-limonene) , limonene degradation I (D-limonene)


Enzymatic reaction of: dihydrocarvone monooxygenase (monocyclic monoterpene ketone monooxygenase)

a dihydrocarvone + NADPH + H+ + oxygen <=> a 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: (4S)-carveol and (4S)-dihydrocarveol degradation , (4R)-carveol and (4R)-dihydrocarveol degradation


Enzymatic reaction of: (iso)-dihydrocarvone monooxygenase (monocyclic monoterpene ketone monooxygenase)

an isodihydrocarvone + NADPH + H+ + oxygen <=> a 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: (4R)-carveol and (4R)-dihydrocarveol degradation


Enzymatic reaction of: menthone monooxygenase (monocyclic monoterpene ketone monooxygenase)

a menthone + NADPH + H+ + oxygen <=> a 7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.


Enzymatic reaction of: (+)-(1S,4R)-menthone monooxygenase (monocyclic monoterpene ketone monooxygenase)

(+)-menthone + NADPH + H+ + oxygen <=> (4S,7R)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.


Enzymatic reaction of: (-)-menthone monooxygenase (monocyclic monoterpene ketone monooxygenase)

(-)-menthone + NADPH + H+ + oxygen <=> (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.


Enzymatic reaction of: (1S,4R)-iso-dihydrocarvone monooxygenase (monocyclic monoterpene ketone monooxygenase)

(+)-isodihydrocarvone + NADPH + oxygen + H+ <=> (3S,6R)-6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: (4R)-carveol and (4R)-dihydrocarveol degradation

Cofactors or Prosthetic Groups: FAD

Inhibitors (Other): Hg2+ [Van00] , Zn2+ [Van00]

T(opt): 35 °C


Enzymatic reaction of: (-)-dihydrocarvone monooxygenase (monocyclic monoterpene ketone monooxygenase)

(-)-dihydrocarvone + NADPH + oxygen + H+ <=> (3S,6S)-6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: (4S)-carveol and (4S)-dihydrocarveol degradation

Cofactors or Prosthetic Groups: FAD [Van00]

Inhibitors (Other): Hg2+ [Van00] , Zn2+

T(opt): 35 °C

pH(opt): 9 [Van00]


Enzymatic reaction of: (1R,4S)-iso-dihydrocarvone monooxygenase (monocyclic monoterpene ketone monooxygenase)

(-)-isodihydrocarvone + NADPH + H+ + oxygen <=> (4S,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: (4S)-carveol and (4S)-dihydrocarveol degradation

Cofactors or Prosthetic Groups: FAD [Van00]

Inhibitors (Other): Hg2+ [Van00] , Zn2+ [Van00]

Kinetic Parameters:

Substrate
Km (μM)
Citations
NADPH
38.0
[Van00]

T(opt): 35 °C [Van00]

pH(opt): 9


Enzymatic reaction of: (1R,4R)-dihydrocarvone monooxygenase (monocyclic monoterpene ketone monooxygenase)

(+)-dihydrocarvone + NADPH + H+ + oxygen <=> (4R,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is physiologically favored in the direction shown.

In Pathways: (4R)-carveol and (4R)-dihydrocarveol degradation

Cofactors or Prosthetic Groups: FAD [Van00]

Inhibitors (Other): Hg2+ [Van00] , Zn2+ [Van00]

Kinetic Parameters:

Substrate
Km (μM)
Citations
(+)-dihydrocarvone
130.0
[Van00]
NADPH
38.0
[Van00]

T(opt): 35 °C [Van00]

pH(opt): 9 [Van00]


Enzymatic reaction of: (1R,4S)-1-hydroxy-2-oxolimonene monooxygenase (monocyclic monoterpene ketone monooxygenase)

(1S,4R)-1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen <=> (4S)-7-hydroxy-4-isoprenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is physiologically favored in the direction shown.

In Pathways: limonene degradation II (L-limonene)

Cofactors or Prosthetic Groups: FAD [Van00]

Inhibitors (Other): Hg2+ [Van00] , Zn2+ [Van00]

Kinetic Parameters:

Substrate
Km (μM)
Citations
NADPH
38.0
[Van00]
(1S,4R)-1-hydroxymenth-8-en-2-one
10.0
[Van00]

T(opt): 35 °C [Van00]

pH(opt): 9 [Van00]


Enzymatic reaction of: (1S,4R)-1-hydroxy-2-oxolimonene monooxygenase (monocyclic monoterpene ketone monooxygenase)

(1R,4S)-1-hydroxymenth-8-en-2-one + NADPH + H+ + oxygen <=> (4R)-7-hydroxy-4-isoprenyl-7-methyl-2-oxo-oxepanone + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is physiologically favored in the direction shown.

In Pathways: limonene degradation I (D-limonene)

Cofactors or Prosthetic Groups: FAD [Van00]

Activators (Allosteric): Zn2+ [Van00]

Inhibitors (Other): Hg2+ [Van00]

Kinetic Parameters:

Substrate
Km (μM)
Citations
(1R,4S)-1-hydroxymenth-8-en-2-one
130.0
[Van00]
NADPH
38.0
[Van00]

T(opt): 35 °C [Van00]

pH(opt): 9 [Van00]


References

Van00: Van Der Werf MJ (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 Pt 3;693-701. PMID: 10769172


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, BIOCYC13B.