Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Reaction: 1.14.13.105

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: 1.14.13.105

Enzymes and Genes:
monocyclic monoterpene ketone monooxygenase Inferred from experiment ( Rhodococcus erythropolis DCL14 )

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

Most BioCyc compounds have been protonated to a reference pH value of 7.3, and some reactions have been computationally balanced for hydrogen by adding free protons. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Direct generic reaction:
a menthone + NADPH + H+ + oxygen → a 7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (1.14.13.105)

Enzyme Commission Primary Name: monocyclic monoterpene ketone monooxygenase

Enzyme Commission Synonyms: 1-hydroxy-2-oxolimonene 1,2-monooxygenase, dihydrocarvone 1,2-monooxygenase, MMKMO

Standard Gibbs Free Energy (ΔrG in kcal/mol): -93.320526 Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
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 [Van00]. 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 [vanderWerf99].

Citations: [vanderWerf00]

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#)

Unification Links: KEGG:R08925 , Rhea:32431

Relationship Links: BRENDA:EC:1.14.13.105 , ENZYME:EC:1.14.13.105 , IUBMB-ExplorEnz:EC:1.14.13.105


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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

vanderWerf00: van der Werf MJ, Boot AM (2000). "Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14." Microbiology 146 ( Pt 5);1129-41. PMID: 10832640

vanderWerf99: van der Werf MJ, Swarts HJ, de Bont JA (1999). "Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene." Appl Environ Microbiol 65(5);2092-102. PMID: 10224006


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 Fri Dec 19, 2014, biocyc14.