1.14.13.160: (2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenase
This is an abbreviated version!
For detailed information about (2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.160
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1.14.13.160
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baeyer-villiger
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bvmos
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cyclohexanone
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lactone
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ketones
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putida
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camphor
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regiodivergent
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biooxidations
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bicyclic
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fad
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biocatalysts
- 1.14.13.160
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baeyer-villiger
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bvmos
- cyclohexanone
- lactone
- ketones
- putida
- camphor
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regiodivergent
-
biooxidations
-
bicyclic
- fad
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biocatalysts
Reaction
Synonyms
2-oxo-DELTA3-4,5,5-trimethylcyclopentenyl-acetyl-CoA monooxygenase, 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA 1,2-monooxygenase, 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA monooxygenase, OTEMO
ECTree
Advanced search results
Substrates Products
Substrates Products on EC 1.14.13.160 - (2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenase
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REACTION DIAGRAM
2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
62% conversion
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-
?
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA + O2 + NADPH + H+
? + NADP+ + H2O
-
-
-
?
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA + O2 + NADPH + H+
delta-lactone of 5-hydroxy-3,4,4-trimethyl-A2-pimelyl-CoA + NADP+ + H2O
2-oxocyclopentyl acetic acid + O2 + NADPH + H+
(6-oxotetrahydro-2H-pyran-2-yl)acetic acid + NADP+ + H2O
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-
-
?
2-oxocyclopentyl ethyl acetate + O2 + NADPH + H+
ethyl (6-oxotetrahydro-2H-pyran-2-yl)acetate + NADP+ + H2O
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-
-
?
3-methyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
13% conversion
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-
?
4-methylcyclohexanone + O2 + NADPH + H+
5-methyloxepan-2-one + NADP+ + H2O
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + O2 + NADPH + H+
? + NADP+ + H2O
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products are a mixture of normal to abnormal lactone at a ratio of 3:1
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?
[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA + O2 + NADPH + H+
[(2R)-3,3,4-trimethyl-6-oxo-3,6-dihydro-1H-pyran-2-yl]acetyl-CoA + NADP+ + H2O
? + NADP+ + H2O
-
-
-
?
(+-)-cis-bicyclo[3.2.0]hept-2-en-6-one + O2 + NADPH + H+
? + NADP+ + H2O
-
-
-
?
? + NADP+ + H2O
34% conversion
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-
?
2,3,4,5-tetramethyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
34% conversion
-
-
?
? + NADP+ + H2O
74% conversion
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-
?
2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
74% conversion
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-
?
6-ethyltetrahydro-2H-pyran-2-one + NADP+ + H2O
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both enantiomers of 2-ethyl cyclohexanone are oxidized at nearly the same rate although giving a low enantiomeric ratio
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?
2-ethylcyclopentanone + O2 + NADPH + H+
6-ethyltetrahydro-2H-pyran-2-one + NADP+ + H2O
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both enantiomers of 2-ethyl cyclohexanone are oxidized at nearly the same rate although giving a low enantiomeric ratio
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?
7-methyloxepan-2-one + NADP+ + H2O
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-
-
?
2-methylcyclohexanone + O2 + NADPH + H+
7-methyloxepan-2-one + NADP+ + H2O
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-
-
?
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
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-
-
?
2-n-hexylcyclopentanone + O2 + NADPH + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
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-
-
?
? + NADP+ + H2O
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-
-
?
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid + O2 + NADPH + H+
? + NADP+ + H2O
-
-
-
?
delta-lactone of 5-hydroxy-3,4,4-trimethyl-A2-pimelyl-CoA + NADP+ + H2O
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specific substrate
monooxygenase reaction, catalysis of a biological Baeyer-Villiger reaction with the formation of a lactone. This lactone product is unstable and susceptible to spontaneous ring opening
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?
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA + O2 + NADPH + H+
delta-lactone of 5-hydroxy-3,4,4-trimethyl-A2-pimelyl-CoA + NADP+ + H2O
Pseudomonas putida C1 / ATCC 17453
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specific substrate
monooxygenase reaction, catalysis of a biological Baeyer-Villiger reaction with the formation of a lactone. This lactone product is unstable and susceptible to spontaneous ring opening
-
?
? + NADP+ + H2O
22% conversion
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-
?
3,5,5-trimethyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
22% conversion
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-
?
? + NADP+ + H2O
13% conversion
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-
?
3-methyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
13% conversion
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-
?
[(2R)-3,3,4-trimethyl-6-oxo-3,6-dihydro-1H-pyran-2-yl]acetyl-CoA + NADP+ + H2O
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mass spectral analysis of the methyl ester of the product confirmes the insertion of a single oxygen atom
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?
[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA + O2 + NADPH + H+
[(2R)-3,3,4-trimethyl-6-oxo-3,6-dihydro-1H-pyran-2-yl]acetyl-CoA + NADP+ + H2O
Pseudomonas putida C1 / ATCC 17453
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mass spectral analysis of the methyl ester of the product confirmes the insertion of a single oxygen atom
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?
?
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no substrate: 2,5-diketocamphane. Less than 5% of the activity with 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA is displayed with 2-oxo-DELTA3-4,5,5-trimethylcyclo-pentenylacetyl-CoA, 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA (hydrolyzed), 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetate-CoA, 2,5-diketocamphane
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-
?
additional information
?
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reaction of different 4-substituted cyclohexanones with small to medium substituents at the C-4 position in nearly all cases give enantiopure lactones with an excellent yield
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?
additional information
?
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reaction of different 4-substituted cyclohexanones with small to medium substituents at the C-4 position in nearly all cases give enantiopure lactones with an excellent yield
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-
?
additional information
?
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reaction of different 4-substituted cyclohexanones with small to medium substituents at the C-4 position in nearly all cases give enantiopure lactones with an excellent yield
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-
?
additional information
?
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Pseudomonas putida C1 / ATCC 17453
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no substrate: 2,5-diketocamphane. Less than 5% of the activity with 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA is displayed with 2-oxo-DELTA3-4,5,5-trimethylcyclo-pentenylacetyl-CoA, 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA (hydrolyzed), 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetate-CoA, 2,5-diketocamphane
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-
?