Information on EC 1.14.13.16 - cyclopentanone monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.16
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RECOMMENDED NAME
GeneOntology No.
cyclopentanone monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cyclopentanone + NADPH + H+ + O2 = 5-valerolactone + NADP+ + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
cyclopentanone,NADPH:oxygen oxidoreductase (5-hydroxylating, lactonizing)
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CAS REGISTRY NUMBER
COMMENTARY hide
37364-15-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain NCIB 9871
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Manually annotated by BRENDA team
strain NCIB 9871
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1R,5S)-8-oxabicyclo[3.2.1]oct-6-en-3-one + NADPH + O2
(1S,6S)-3,9-dioxabicyclo[4.2.1]non-7-en-4-one + NADP+ + H2O
show the reaction diagram
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
show the reaction diagram
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-
-
-
?
4-acetoxy-cyclohexanone + NADPH + O2
4-acetoxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
4-acetoxycyclohexanone + NADPH + H+ + O2
5-acetoxyoxepan-2-one + NADP+ + H2O
show the reaction diagram
4-allyl-cyclohexanone + NADPH + O2
4-allyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
4-allyloxycyclohexanone + NADPH + H+ + O2
5-allyloxyoxepan-2-one + NADP+ + H2O
show the reaction diagram
4-benzyloxycyclohexanone + NADPH + H+ + O2
5-benzyloxyoxepan-2-one + NADP+ + H2O
show the reaction diagram
4-chlorocyclohexanone + NADPH + H+ + O2
5-chlorooxepan-2-one + NADP+ + H2O
show the reaction diagram
4-ethoxy-cyclohexanone + NADPH + O2
4-ethoxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
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-
-
-
?
4-ethoxycyclohexanone + NADPH + H+ + O2
5-ethoxyoxepane-2-one + NADP+ + H2O
show the reaction diagram
4-ethyl-cyclohexanone + NADPH + O2
4-ethyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
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-
-
-
?
4-hydroxy-4-allyl-cyclohexanone + NADPH + O2
?
show the reaction diagram
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-
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?
4-hydroxy-4-ethyl-cyclohexanone + NADPH + O2
?
show the reaction diagram
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-
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?
4-hydroxy-4-methyl-cyclohexanone + NADPH + O2
?
show the reaction diagram
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-
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
4-methoxy-cyclohexanone + NADPH + O2
4-methoxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
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-
-
-
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
4-n-propyl-cyclohexanone + NADPH + O2
4-n-propyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
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?
butan-2-one + NADPH + O2
?
show the reaction diagram
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?
cyclobutanone + NADPH + O2
butyrolactone + NADP+ + H2O
show the reaction diagram
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?
cycloheptanone + NADPH + O2
1-oxa-2-oxocyclooctane + NADP+ + H2O
show the reaction diagram
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poor substrate
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-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
show the reaction diagram
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-
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?
cyclooctanone + NADPH + O2
1-oxa-2-oxocyclononane + NADP+ + H2O
show the reaction diagram
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poor substrate
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?
cyclopentanone + NADPH + H+ + O2
5-valerolactone + NADP+ + H2O
show the reaction diagram
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?
cyclopentanone + NADPH + O2
5-valerolactone + NADP+ + H2O
show the reaction diagram
norbornanone + NADPH + O2
?
show the reaction diagram
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?
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
cyclopentanone + NADPH + O2
5-valerolactone + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,5'-dithiobis(2-nitrobenzoate)
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arsenite
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Bathocuproine
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bathophenanthroline
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diethyldithiocarbamate
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iodoacetamide
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p-hydroxymercuribenzoate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.15
Cyclopentanone
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0.001
O2
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 7.5
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
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alpha4, 4 * 50000, SDS-Page
194000
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ultracentrifugation
200000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homotetramer
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alpha4, 4 * 50000, SDS-Page
trimer or tetramer
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3 or 4 * 54000-58000, SDS-PAGE
additional information
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
reduction of enzyme by visible light in presence of EDTA
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439017
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expression in Escherichia coli
overexpression in Escherichia coli
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overexpression of wild-type and mutant enzymes in Escherichia coli
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overexpression of wild-type and mutants in strains BL121(DE3) and JM109
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F156H/G157L
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
F156L/G157F
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site-directed mutagenesis, the mutations improve the hydrophobic active site pocket increasing enzyme selectivity and stereospecificity
F156N/G157Y
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
F450C
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
F450I
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
G119S/F450Y
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
F156N/G157Y
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
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F450C
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
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F450I
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
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G119S/F450Y
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site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme
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additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis