BRENDA - Enzyme Database show
show all sequences of 1.14.13.92

Selective Baeyer-Villiger oxidation of racemic ketones in aqueous-organic media catalyzed by phenylacetone monooxygenase

Rodriguez, C.; de Gonzalo, G.; Torres Pazmino, D.E.; Fraaije, M.W.; Gotor, V.; Tetrahedron Asymmetry 19, 197-203 (2008)
No PubMed abstract available

Data extracted from this reference:

Application
Application
Commentary
Organism
synthesis
the enzyme is useful for kinetic resolution of a set of racemic substituted 3-phenylbutan-2-ones and synthesis of enantiopure compounds, overview
Thermobifida fusca
Inhibitors
Inhibitors
Commentary
Organism
Structure
additional information
effects of a range of solvents on the biocatalytic properties of the biocatalyst, overview
Thermobifida fusca
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
phenylacetone + NADPH + H+ + O2
Thermobifida fusca
-
benzyl acetate + NADP+ + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Thermobifida fusca
-
-
-
Reaction
Reaction
Commentary
Organism
phenylacetone + NADPH + H+ + O2 = benzyl acetate + NADP+ + H2O
reaction mechanism and catalytic cycle, rapid binding of NADPH is followed by a transfer of the (4R)-hydride from NADPH to the FAD cofactor. The reduced PAMO is rapidly oxygenated by molecular oxygen, yielding a C4a-peroxyflavin. The peroxyflavin enzyme intermediate, possibly a Criegee intermediate or a C4a-hydroxyflavin form, reacts with phenylacetone to form benzylacetate, residue R337 is important in catalysis, overview
Thermobifida fusca
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(R)-2-acetoxyphenylacetonitrile + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
(R)-3-(4-bromophenyl)butan-2-one + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
(S)-1-(3-trifluoromethylphenyl)ethyl acetate + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
3-(3-trifluoromethylphenyl)butan-2-one + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
3-phenyl-2-butanone + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
(R)-3-phenylbutan-2-one + (S)-1-phenyethyl acetate
-
-
-
?
alpha-acetylphenylacetonitrile + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
(R)-2-acetoxyphenylacetonitrile + NADP+ + H2O
enantiopure product formation
-
-
?
phenylacetone + NADPH + H+ + O2
-
690110
Thermobifida fusca
benzyl acetate + NADP+ + H2O
-
-
-
?
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
assay at
Thermobifida fusca
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Thermobifida fusca
Cofactor
Cofactor
Commentary
Organism
Structure
NADPH
-
Thermobifida fusca
Application (protein specific)
Application
Commentary
Organism
synthesis
the enzyme is useful for kinetic resolution of a set of racemic substituted 3-phenylbutan-2-ones and synthesis of enantiopure compounds, overview
Thermobifida fusca
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADPH
-
Thermobifida fusca
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
additional information
effects of a range of solvents on the biocatalytic properties of the biocatalyst, overview
Thermobifida fusca
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
phenylacetone + NADPH + H+ + O2
Thermobifida fusca
-
benzyl acetate + NADP+ + H2O
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(R)-2-acetoxyphenylacetonitrile + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
(R)-3-(4-bromophenyl)butan-2-one + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
(S)-1-(3-trifluoromethylphenyl)ethyl acetate + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
3-(3-trifluoromethylphenyl)butan-2-one + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
?
-
-
-
?
3-phenyl-2-butanone + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
(R)-3-phenylbutan-2-one + (S)-1-phenyethyl acetate
-
-
-
?
alpha-acetylphenylacetonitrile + NADPH + H+ + O2
enantioselective reaction
690110
Thermobifida fusca
(R)-2-acetoxyphenylacetonitrile + NADP+ + H2O
enantiopure product formation
-
-
?
phenylacetone + NADPH + H+ + O2
-
690110
Thermobifida fusca
benzyl acetate + NADP+ + H2O
-
-
-
?
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
assay at
Thermobifida fusca
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Thermobifida fusca
Other publictions for EC 1.14.13.92
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
745991
Carvalho
Catalytic mechanism of phenyl ...
Thermobifida fusca
Phys. Chem. Chem. Phys.
19
26851-26861
2017
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744548
Parra
Directed evolution of phenyla ...
Thermobifida fusca
Biotechnol. Bioeng.
112
1354-1364
2015
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20
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2
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20
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3
2
1
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1
1
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2
2
726793
Dudek
Extending the substrate scope ...
Thermobifida fusca
Appl. Microbiol. Biotechnol.
98
4009-4020
2013
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1
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2
8
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1
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15
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8
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8
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15
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1
8
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8
8
727379
de Gonzalo
Improvement of the biocatalyti ...
Thermobifida fusca
Enzyme Microb. Technol.
50
43-49
2012
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728164
Rodriguez
-
Optimization of oxidative bioc ...
Thermobifida fusca
J. Mol. Catal. B
74
138-143
2012
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726716
Dudek
Mapping the substrate binding ...
Thermobifida fusca
Appl. Environ. Microbiol.
77
5730-5738
2011
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30
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30
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3
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728163
Andrade
-
Oxidation of organoselenium co ...
Thermobifida fusca
J. Mol. Catal. B
73
63-66
2011
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1
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710979
Dudek
Investigating the coenzyme spe ...
Thermobifida fusca
Appl. Microbiol. Biotechnol.
88
1135-1143
2010
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1
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15
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14
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15
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14
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1
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12
1
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15
15
697754
Rioz-Martinez
-
Enzymatic Baeyer-Villiger oxid ...
Pseudomonas fluorescens, Thermobifida fusca
Eur. J. Org. Chem.
2009
2526-2532
2009
1
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2
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1
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1
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10
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2
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698487
Reetz
Laboratory evolution of robust ...
Thermobifida fusca
J. Am. Chem. Soc.
131
15424-15432
2009
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1
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7
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1
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685231
Torres Pazmino
Kinetic mechanism of phenylace ...
Thermobifida fusca
Biochemistry
47
4082-4093
2008
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2
1
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2
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1
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690110
Rodriguez
-
Selective Baeyer-Villiger oxid ...
Thermobifida fusca
Tetrahedron Asymmetry
19
197-203
2008
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1
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1
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1
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1
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678885
Rehdorf
Cloning, expression and charac ...
Pseudomonas putida, Pseudomonas putida KT 2240
Biotechnol. Lett.
29
1393-1398
2007
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11
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42
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14
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14
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1
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684245
Zambianchi
-
Titration and assignment of re ...
Thermobifida fusca
Adv. Synth. Catal.
349
1327-1331
2007
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675467
De Gonzalo
-
Biocatalytic properties of Bae ...
Thermobifida fusca
J. Mol. Catal. B
39
91-97
2006
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657625
Fraaije
Discovery of a thermostable Ba ...
Thermobifida fusca
Appl. Microbiol. Biotechnol.
66
393-400
2005
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7
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671189
Bocola
-
Converting phenylacetone monoo ...
Thermobifida fusca
Adv. Synth. Catal.
347
979-986
2005
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1
1
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7
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671682
Schulz
Towards practical biocatalytic ...
Thermobifida fusca
Beilstein J. Org. Chem.
1
10
2005
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1
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1
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1
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4
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677171
de Gonzalo
-
Oxidations catalyzed by phenyl ...
Thermobifida fusca
Tetrahedron
16
3077-3083
2005
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1
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9
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9
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1
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659371
Fraaije
The prodrug activator EtaA fro ...
Mycobacterium tuberculosis
J. Biol. Chem.
279
3354-3360
2004
1
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1
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2
5
1
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1
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1
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12
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5
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2
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1
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2
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2
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5
1
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660361
Malito
Crystal structure of a Baeyer- ...
Thermobifida fusca
Proc. Natl. Acad. Sci. USA
101
13157-13162
2004
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