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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:

Rhodococcus erythropolis DCL14 : monocyclic monoterpene ketone monooxygenase Inferred from experiment

Note that this reaction equation differs from the official Enzyme Commission reaction equations for this EC number, which can be found here , here , here , here and here .

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.

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: ?

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

i4: (+)-dihydrocarvone + NADPH + H+ + oxygen → (4R,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: (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#)

i2: (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#)

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 19.0 on Tue Sep 1, 2015, biocyc13.