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Information on EC 1.14.13.16 - cyclopentanone monooxygenase and Organism(s) Comamonas sp. and UniProt Accession Q8GAW0

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Comamonas sp.
UNIPROT: Q8GAW0 not found.
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The taxonomic range for the selected organisms is: Comamonas sp.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
cyclopentanone monooxygenase, cyclopentanone oxygenase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclopentanone monooxygenase
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cyclopentanone oxygenase
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-
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additional information
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the enzyme belongs to the flavin-containing Baeyer–Villiger monooxygenases, BVMOs
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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oxidation
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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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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
?
(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
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stereospecific (1S,6S)-product formation
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?
4-acetoxycyclohexanone + NADPH + H+ + O2
5-acetoxyoxepan-2-one + 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
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-
-
-
?
4-ethoxycyclohexanone + NADPH + H+ + O2
5-ethoxyoxepane-2-one + NADP+ + H2O
show the reaction diagram
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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
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?
NATURAL SUBSTRATE
NATURAL PRODUCT
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
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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completion of the formal total synthesis of (+)-showdomycin and establishing of the absolute configuration of biooxidation product as (1S,6S)-3,9-dioxabicyclo[4.2.1]non-7-en-4-one, overview
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
expressed in Escherichia coli
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overexpression in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
Baeyer-Villiger biooxidation of 4-methylcyclohexanone to 5-methyloxepane-2-one catalysed by recombinant Escherichia coli overexpressing cyclopentanone monooxygenase encapsulated in polyelectrolyte complex capsules. Viability of encapsulated cells decreases with increasing substrate concentration from 99 to 83%, while substrate conversions decrease from 100 to 6%. Storage stabilization of encapsulated cells is observed by increased substrate conversion form 68 to 96%
synthesis
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Iwaki, H.; Hasegawa, Y.; Wang, S.; Kayser, M.M.; Lau, P.C.K.
Cloning and characterization of a gene cluster involved in cyclopentanol metabolism in Comamonas sp. strain N.C.I.M.B. 9872 and biotransformations effected by Eschericha coli-expressed cyclopentanone 1,2-monooxygenase
Appl. Environ. Microbiol.
68
5671-5684
2002
Comamonas sp.
Manually annotated by BRENDA team
Wang, S.; Kayser, M.M.; Iwaki, H.; Lau, P.C.K.
Monooxygenase-catalyzed Baeyer-Villiger oxidations: CHMO versus CPMO
J. Mol. Catal. B
22
211-218
2003
Comamonas sp.
-
Manually annotated by BRENDA team
Mihovilovic, M.D.; Bianchi, D.A.; Rudroff, F.
Accessing tetrahydrofuran-based natural products by microbial Baeyer-Villiger biooxidation
Chem. Commun. (Camb. )
1
3214-3216
2006
Comamonas sp.
Manually annotated by BRENDA team
Clouthier, C.M.; Kayser, M.M.
Biotransformations with engineered E. coli cells expressing wild-type and mutant Baeyer-Villiger monooxygenases under non-growing conditions
J. Mol. Catal. B
46
32-36
2007
Comamonas sp.
-
Manually annotated by BRENDA team
Schenkmayerova, A.; Bucko, M.; Gemeiner, P.; Katrlik, J.
Microbial monooxygenase amperometric biosensor for monitoring of Baeyer-Villiger biotransformation
Biosens. Bioelectron.
50
235-238
2013
Comamonas sp. (Q8GAW0)
Manually annotated by BRENDA team