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Information on EC 1.14.13.160 - (2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenase
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EC Tree
1.14.13.160 (2,2,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA 1,5-monooxygenaseIUBMB Comments
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.
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Word Map
- 1.14.13.160
-
baeyer-villiger
-
bvmos
- cyclohexanone
- lactone
- ketones
- putida
- camphor
-
regiodivergent
-
biooxidations
-
bicyclic
- fad
-
biocatalysts
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
Synonyms
otemo, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
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
2-oxo-DELTA3-4,5,5-trimethylcyclopentenyl-acetyl-CoA monooxygenase
Pseudomonas putida C1 / ATCC 17453
-
-
-
OTEMO
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
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
-
-
-
-
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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.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
62% conversion
-
-
?
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
-
-
-
?
2-oxocyclopentyl ethyl acetate + O2 + NADPH + H+
ethyl (6-oxotetrahydro-2H-pyran-2-yl)acetate + NADP+ + H2O
-
-
-
?
3-methyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
13% conversion
-
-
?
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
-
products are a mixture of normal to abnormal lactone at a ratio of 3:1
-
?
[(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
(+-)-cis-bicyclo[3.2.0]hept-2-en-6-one + O2 + NADPH + H+
? + NADP+ + H2O
-
-
-
?
(+-)-cis-bicyclo[3.2.0]hept-2-en-6-one + O2 + NADPH + H+
? + NADP+ + H2O
-
-
-
?
2,3,4,5-tetramethyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
34% conversion
-
-
?
2,3,4,5-tetramethyl-2-cyclopenten-1-one + O2 + NADPH + H+
? + NADP+ + H2O
34% conversion
-
-
?
2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
74% conversion
-
-
?
2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
74% conversion
-
-
?
2-ethylcyclopentanone + O2 + NADPH + H+
6-ethyltetrahydro-2H-pyran-2-one + NADP+ + H2O
-
both enantiomers of 2-ethyl cyclohexanone are oxidized at nearly the same rate although giving a low enantiomeric ratio
-
?
2-ethylcyclopentanone + O2 + NADPH + H+
6-ethyltetrahydro-2H-pyran-2-one + NADP+ + H2O
-
both enantiomers of 2-ethyl cyclohexanone are oxidized at nearly the same rate although giving a low enantiomeric ratio
-
?
2-methylcyclohexanone + O2 + NADPH + H+
7-methyloxepan-2-one + NADP+ + H2O
-
-
-
?
2-methylcyclohexanone + O2 + NADPH + H+
7-methyloxepan-2-one + NADP+ + H2O
-
-
-
?
2-n-hexylcyclopentanone + O2 + NADPH + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
-
-
-
?
2-n-hexylcyclopentanone + O2 + NADPH + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
-
-
-
?
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid + O2 + NADPH + H+
? + NADP+ + H2O
-
-
-
?
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid + 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
-
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
-
?
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
-
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
-
?
3,5,5-trimethyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
22% conversion
-
-
?
3,5,5-trimethyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
22% conversion
-
-
?
3-methyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
13% conversion
-
-
?
3-methyl-2-cyclohexen-1-one + O2 + NADPH + H+
? + NADP+ + H2O
13% conversion
-
-
?
[(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
-
-
mass spectral analysis of the methyl ester of the product confirmes the insertion of a single oxygen atom
-
?
[(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
-
-
mass spectral analysis of the methyl ester of the product confirmes the insertion of a single oxygen atom
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
Pseudomonas putida C1 / ATCC 17453
-
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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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
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
[(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
-
-
-
-
?
[(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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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
Crystallization data. With the exception of the O2' atom of ribose and the C-8 and N-9 atoms of adenine, the FAD cofactor is completely buried and inaccessible to the solvent
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
protein contains less than 0.1 atom of Fe per molecule
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.16
2-methylcyclohexanone
pH 9.0, temperature not specified in the publication
0.018
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA
pH 9.0, temperature not specified in the publication
0.31
2-oxocyclopentyl ethyl acetate
pH 9.0, temperature not specified in the publication
1.4
4-methylcyclohexanone
pH 9.0, temperature not specified in the publication
0.03
2-n-hexylcyclopentanone
pH 9.0, temperature not specified in the publication
0.6
2-n-hexylcyclopentanone
pH 9.0, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.9
2-methylcyclohexanone
pH 9.0, temperature not specified in the publication
0.13
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid
pH 9.0, temperature not specified in the publication
4.8
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA
pH 9.0, temperature not specified in the publication
0.11
2-oxocyclopentyl acetic acid
pH 9.0, temperature not specified in the publication
6.9
2-oxocyclopentyl ethyl acetate
pH 9.0, temperature not specified in the publication
5.6
4-methylcyclohexanone
pH 9.0, temperature not specified in the publication
1.8
2-n-hexylcyclopentanone
pH 9.0, temperature not specified in the publication
13.6
2-n-hexylcyclopentanone
pH 9.0, temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
5.5
2-methylcyclohexanone
pH 9.0, temperature not specified in the publication
270
2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-CoA
pH 9.0, temperature not specified in the publication
22
2-oxocyclopentyl ethyl acetate
pH 9.0, temperature not specified in the publication
4
4-methylcyclohexanone
pH 9.0, temperature not specified in the publication
3
2-n-hexylcyclopentanone
pH 9.0, temperature not specified in the publication
430
2-n-hexylcyclopentanone
pH 9.0, temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
inducible enzyme, no or poor activity in succinate- and octanoate-grown cells
brenda
Pseudomonas putida C1 / ATCC 17453
-
inducible enzyme, no or poor activity in succinate- and octanoate-grown cells
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
metabolism
-
the enzyme catalyzes a step in the (+)-camphor catabolism. Metabolism of the first ring cleavage intermediate, 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid, occurs through the sequential action of two inducible enzymes, a coenzyme A ester synthetase, EC 6.2.1.38, and the monooxygenase
metabolism
Pseudomonas putida C1 / ATCC 17453
-
the enzyme catalyzes a step in the (+)-camphor catabolism. Metabolism of the first ring cleavage intermediate, 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid, occurs through the sequential action of two inducible enzymes, a coenzyme A ester synthetase, EC 6.2.1.38, and the monooxygenase
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A084G354_PSEDA
564
0
63762
TrEMBL
other Location (Reliability: 3)
A0A6J5GNC1_9BURK
560
0
62321
TrEMBL
-
A0A6B9B9F1_MYCAV
493
0
55239
TrEMBL
-
A0A1C0TY50_9GAMM
604
0
69131
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
106000
60000
x * 60000, SDS-PAGE, x * 63500, calculated, both for His-tagged protein
63500
x * 60000, SDS-PAGE, x * 63500, calculated, both for His-tagged protein
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
homodimer
?
x * 60000, SDS-PAGE, x * 63500, calculated, both for His-tagged protein
?
-
x * 60000, SDS-PAGE, x * 63500, calculated, both for His-tagged protein
-
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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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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
the ability to grow on (+)-camphor is transferred to a recipient strain, Pseudomonas putida PaW340, which is a streptomycin-resistant tryptophan auxotroph that is derived from Pseudomonas putida (arvilla) mt-2
additional information
Pseudomonas putida C1 / ATCC 17453
-
the ability to grow on (+)-camphor is transferred to a recipient strain, Pseudomonas putida PaW340, which is a streptomycin-resistant tryptophan auxotroph that is derived from Pseudomonas putida (arvilla) mt-2
-
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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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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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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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
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
-
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
Pseudomonas putida C1 / ATCC 17453
-
-
the enzyme is induced by cell growth on (+)-camphor as carbon source
Pseudomonas putida C1 / ATCC 17453
-
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Leisch, H.; Shi, R.; Grosse, S.; Morley, K.; Bergeron, H.; Cygler, M.; Iwaki, H.; Hasegawa, Y.; Lau, P.C.
Cloning, Baeyer-Villiger biooxidations, and structures of the camphor pathway 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase of Pseudomonas putida ATCC 17453
Appl. Environ. Microbiol.
78
2200-2212
2012
Pseudomonas putida (H3JQW0), Pseudomonas putida ATCC 17453 (H3JQW0), Pseudomonas putida ATCC 17453
brenda
Kadow, M.; Loschinski, K.; Sass, S.; Schmidt, M.; Bornscheuer, U.
Completing the series of BVMOs involved in camphor metabolism of Pseudomonas putida NCIMB 10007 by identification of the two missing genes, their functional expression in E. coli, and biochemical characterization
Appl. Microbiol. Biotechnol.
96
419-429
2012
Pseudomonas putida (H3JQW0), Pseudomonas putida NCIMB 10007 (H3JQW0), Pseudomonas putida NCIMB 10007
brenda
Ougham, H.; Taylor, D.; Trudgill, P.
Camphor revisited: Involvement of a unique monooxygenase in metabolism of 2-oxo-DELTA3-4,5,5-trimethylcyclopentenylacetic acid by Pseudomonas putida
J. Bacteriol.
153
140-152
1983
Pseudomonas putida, no activity in Pseudomonas putida strain PaW340, Pseudomonas putida C1 / ATCC 17453
brenda
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