Information on EC 1.14.13.160 - (2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenase

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The expected taxonomic range for this enzyme is: Pseudomonas putida

EC NUMBER
COMMENTARY hide
1.14.13.160
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RECOMMENDED NAME
GeneOntology No.
(2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
[(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
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(+)-camphor degradation
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(-)-camphor degradation
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SYSTEMATIC NAME
IUBMB Comments
[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA,NADPH:oxygen oxidoreductase (1,5-lactonizing)
A FAD dependent enzyme isolated from Pseudomonas putida. Forms part of the catabolism pathway of camphor. It acts on the CoA ester in preference to the free acid.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
no activity in Pseudomonas putida strain PaW340
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Manually annotated by BRENDA team
ATCC 17453
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+-)-cis-bicyclo[3.2.0]hept-2-en-6-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
2,3,4,5-tetramethyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
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62% conversion
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-
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2-ethylcyclopentanone + O2 + NADPH + H+
6-ethyltetrahydro-2H-pyran-2-one + NADP+ + H2O
show the reaction diagram
2-methylcyclohexanone + O2 + NADPH + H+
7-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
2-n-hexylcyclopentanone + O2 + NADPH + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
show the reaction diagram
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
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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
show the reaction diagram
2-oxocyclopentyl acetic acid + O2 + NADPH + H+
(6-oxotetrahydro-2H-pyran-2-yl)acetic acid + NADP+ + H2O
show the reaction diagram
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2-oxocyclopentyl ethyl acetate + O2 + NADPH + H+
ethyl (6-oxotetrahydro-2H-pyran-2-yl)acetate + NADP+ + H2O
show the reaction diagram
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-
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3,5,5-trimethyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
3-methyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
3-methyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
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13% conversion
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4-methylcyclohexanone + O2 + NADPH + H+
5-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
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bicyclo[3.2.0]hept-2-en-6-one + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
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products are a mixture of normal to abnormal lactone at a ratio of 3:1
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cyclobutanone + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
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norcamphor + O2 + NADPH + H+
? + NADP+ + H2O
show the reaction diagram
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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
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
[(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
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
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specific for; specific for NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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protein contains less than 0.1 atom of Fe per molecule; the enzyme contains no iron
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.028
(+-)-cis-bicyclo[3.2.0]hept-2-en-6-one
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pH 9.0, 20C
0.16
2-methylcyclohexanone
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pH 9.0, temperature not specified in the publication
0.03 - 0.6
2-n-hexylcyclopentanone
0.018
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA
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pH 9.0, temperature not specified in the publication
0.31
2-oxocyclopentyl ethyl acetate
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pH 9.0, temperature not specified in the publication
1.4
4-methylcyclohexanone
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pH 9.0, temperature not specified in the publication
0.127
Cyclobutanone
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pH 9.0, 20C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.9
2-methylcyclohexanone
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
1.8 - 13.6
2-n-hexylcyclopentanone
0.13
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
4.8
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
0.11
2-oxocyclopentyl acetic acid
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
6.9
2-oxocyclopentyl ethyl acetate
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
5.6
4-methylcyclohexanone
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
49.3
(+-)-cis-bicyclo[3.2.0]hept-2-en-6-one
Pseudomonas putida
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pH 9.0, 20C
86849
5.5
2-methylcyclohexanone
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
4471
3 - 430
2-n-hexylcyclopentanone
19621
270
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
28611
22
2-oxocyclopentyl ethyl acetate
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
41960
4
4-methylcyclohexanone
Pseudomonas putida
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pH 9.0, temperature not specified in the publication
3313
14.7
Cyclobutanone
Pseudomonas putida
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pH 9.0, 20C
8076
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.68
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purified enzyme, pH 9.0, 30C
2200
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pH 9.0, 20C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
106000
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analytical sedimentation centrifugation; gel filtration
118000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in complex with flavin adenine dinucleotide at a 1.95 A resolution as well as with bound FAD and NADP+ at a 2.0 A resolution. Crystal forms reveal a conformational plasticity of several loop regions
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
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half-life 196 min
25
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half-life 43 min
30
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half-life 9 min
35
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stable up to
40
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half-life 3.8 min
45
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half-life below 0.4 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, 24 h, 50% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; native enzyme 84fold to homogeneity by ammonium sulfate fractionation, anion exchange chromatography, gel filtration, again ammonium sulfate fractionation, and affinity chromatography
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recombinant enzyme
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recombinant protein
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme is induced by growth with (+)-camphor or 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid, but undetectable in extracts of octanoate- and succinate-grown cells; the enzyme is induced by cell growth on (+)-camphor as carbon source
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information