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Information on EC 1.14.13.84 - 4-hydroxyacetophenone monooxygenase
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EC Tree
1.14.13.84 4-hydroxyacetophenone monooxygenaseIUBMB Comments
Contains FAD. The enzyme from Pseudomonas fluorescens ACB catalyses the conversion of a wide range of acetophenone derivatives. Highest activity occurs with compounds bearing an electron-donating substituent at the para position of the aromatic ring . In the absence of substrate, the enzyme can act as an NAD(P)H oxidase (EC 1.6.3.1).
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Word Map
- 1.14.13.84
-
baeyer-villiger
- fluorescens
- ketones
-
bvmos
- acetophenones
- cyclohexanone
-
nadph-dependent
-
biocatalytic
- putida
-
enantioselectivity
- resin
-
base-catalysed
-
stabilised
-
ring-substituted
-
characterise
- fad
- flavoproteins
- synthesis
- 4-fluorophenol
-
fluorophenyl
- fluoride
-
flavin-containing
-
synthons
- 4-fluorocatechol
- sulfides
- lactones
-
fluorinated
-
noncovalent
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
hapmo, 4-hydroxyacetophenone monooxygenase, arylketone monooxygenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-hydroxyacetophenone monooxygenase
arylketone monooxygenase
Baeyer-Villiger monooxygenase
hAPA
HAPMO
oxygenase, 4-hydroxyacetophenone mono-
additional information
HAPMO
-
-
-
-
additional information
-
the enzyme is a BaeyerVilliger monooxygenase
additional information
-
the enzyme is a BaeyerVilliger monooxygenase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
reaction mechanism
-
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
enantioselectivity
-
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
Contains FAD. The enzyme from Pseudomonas fluorescens ACB catalyses the conversion of a wide range of acetophenone derivatives. Highest activity occurs with compounds bearing an electron-donating substituent at the para position of the aromatic ring [1]. In the absence of substrate, the enzyme can act as an NADPH oxidase (EC 1.6.3.1)
-
-
-
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
contains FAD, the enzyme from Pseudomonas fluorescens ACB catalyses the conversion of a wide range of acetophenone derivatives, highest activity occurs with compounds bearing an electron-donating substituent at the para position of the aromatic ring, in the absence of substrate, the enzyme can act as an NADPH oxidase (EC 1.6.3.1)
-
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
contains FAD, the enzyme from Pseudomonas fluorescens ACB catalyses the conversion of a wide range of acetophenone derivatives, highest activity occurs with compounds bearing an electron-donating substituent at the para position of the aromatic ring, in the absence of substrate, the enzyme can act as an NADPH oxidase (EC 1.6.3.1)
-
-
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
enantioselectivity
-
-
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
reaction mechanism
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Baeyer-Villiger reaction
oxidation
redox reaction
-
-
-
-
reduction
oxidation
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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-
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SYSTEMATIC NAME
IUBMB Comments
(4-hydroxyphenyl)ethan-1-one,NADPH:oxygen oxidoreductase (ester-forming)
Contains FAD. The enzyme from Pseudomonas fluorescens ACB catalyses the conversion of a wide range of acetophenone derivatives. Highest activity occurs with compounds bearing an electron-donating substituent at the para position of the aromatic ring [1]. In the absence of substrate, the enzyme can act as an NAD(P)H oxidase (EC 1.6.3.1).
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CAS REGISTRY NUMBER
COMMENTARY
156621-13-5
-
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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
1-bromo-indanone + NADPH + H+ + O2
6-bromoisochroman-1-one + NADP+ + H2O
-
substrate is only accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
2,4-pentanedione + NADPH + H+ + O2
?
-
very poor substrate
-
?
2,4-pentanedione + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
2-acetylpyrrole + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
2-chloro-thioanisole + NADPH + H+ + O2
2-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O
-
-
96% enantiomeric excess
-
?
2-chloroethyl phenyl sulfide + NADPH + H+ + O2
2-chloroethyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
81% enantiomeric excess
-
?
2-decanone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
2-phenylpropionaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
3'-hydroxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
3-aminoacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
3-chloro-2-butanone + NADPH + H+ + O2
?
-
very poor substrate
-
?
3-chloro-thioanisole + NADPH + H+ + O2
3-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
3-hydroxyacetophenone + NADPH + H+ + O2
3-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
3-methoxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
3-nitroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
3-phenyl-2-butanone + NADPH + H+ + O2
1-phenylethyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
3-phenyl-2-pentanone + NADPH + H+ + O2
1-phenylpropyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
4-acetylpyridine + NADPH + H+ + O2
?
-
very poor substrate
-
?
4-amino-thioanisole + NADPH + H+ + O2
4-[(S)-methylsulfinyl]aniline + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
4-aminoacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-chloro-thioanisole + NADPH + H+ + O2
4-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O
-
-
96% enantiomeric excess
-
?
4-chloro-thioanisole + NADPH + H+ + O2
4-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-chloroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-cyano-thioanisole + NADPH + H+ + O2
4-cyanophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-cyano-thioanisole + NADPH + H+ + O2
4-[(S)-methylsulfinyl]benzonitrile + NADP+ + H2O
-
-
96% enantiomeric excess
-
?
4-fluoroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-hydroxy-2-decanone + NADPH + H+ + O2
2-hydroxyoctyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
4-hydroxy-2-nonanone + NADPH + H+ + O2
2-hydroxyheptyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
4-hydroxy-2-octanone + NADPH + H+ + O2
2-hydroxyhexyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
4-hydroxy-2-undecanone + NADPH + H+ + O2
2-hydroxynonyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
4-hydroxy-3-methylacetophenone + NADPH + H+ + O2
4-hydroxy-3-methylphenyl acetate + NADP+ + H2O
4-hydroxy-4-phenyl-2-butanone + NADPH + H+ + O2
1-hydroxy-1-phenylethyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 25°C
-
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
?
strictly NADPH-dependent
-
?
4-methoxy-thioanisole + NADPH + H+ + O2
4-methoxyphenyl methyl (S)-sulfoxide + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
4-methoxy-thioanisole + NADPH + H+ + O2
4-methoxyphenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-methoxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-methyl-thioanisole + NADPH + H+ + O2
4-methylphenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-methyl-thioanisole + NADPH + H+ + O2
methyl 4-methylphenyl (S)-sulfoxide + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
4-methylacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-nitro-thioanisole + NADPH + H+ + O2
4-nitrophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-nitro-thioanisole + NADPH + H+ + O2
methyl 4-nitrophenyl (S)-sulfoxide + NADP+ + H2O
-
-
87% enantiomeric excess
-
?
4-nitroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
5-bromo-1-indanone + NADPH + H+ + O2
5-bromo-3,4-dihydrochromen-2-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h lower activity than towards chlorine derivative, with 5% hexane 52% conversion
-
?
5-chloro-1-indanone + NADPH + H+ + O2
5-chloro-3,4-dihydrochromen-2-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h lower conversion without cosolvent than with 5% hexane (87% conversion)
-
?
5-methoxy-1-indanone + NADPH + H+ + O2
5-methoxy-3,4-dihydrochromen-2-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h with 5% hexane 32% conversion
-
?
6-chloro-1-indanone + NADPH + H+ + O2
7-chloro-3,4-dihydrochromen-2-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h higher conversion without cosolvent than with 5% hexane (56% conversion)
-
?
6-methoxy-1-indanone + NADPH + H+ + O2
6-methoxy-3,4-dihydrochromen-2-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h with 5% hexane 32% conversion
-
?
6-methoxy-1-indanone + NADPH + H+ + O2
? + NADP+ + H2O
-
substrate is only accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
acetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
benzaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
benzaldehyde + NADPH + H+ + O2
phenyl formate + NADP+ + H2O
-
-
-
?
benzocyclobutanone + NADPH + H+ + O2
2-coumaranone + NADP+ + H2O
-
reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
benzocyclobutanone + NADPH + H+ + O2
coumaranone + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h 87% conversion, with 5% hexane 93% conversion
-
?
benzyl 1-methylethyl sulfide + NADPH + H+ + O2
benzyl 1-methylethyl (R)-sulfoxide + NADP+ + H2O
-
-
82% enantiomeric excess
-
?
benzyl butyl sulfide + NADPH + H+ + O2
benzyl butyl (R)-sulfoxide + NADP+ + H2O
-
-
77% enantiomeric excess
-
?
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl (S)-sulfoxide + NADP+ + H2O
-
-
81% enantiomeric excess
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl (S)-sulfoxide + NADP+ + H2O
-
-
85% enantiomeric excess
-
?
benzyl propyl sulfide + NADPH + H+ + O2
benzyl propyl (R)-sulfoxide + NADP+ + H2O
-
-
65% enantiomeric excess
-
?
bicyclohept-2-en-6-one + NADPH + H+ + O2
?
-
enantioselectivity, preferably converts (1R,5S)-bicyclohept-2-en-6-one with an enantiomeric ratio (E) of 20
-
?
butyl phenyl sulfide + NADPH + H+ + O2
butyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
71% enantiomeric excess
-
?
butyrophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
butyrophenone + NADPH + H+ + O2
phenyl butyrate + NADP+ + H2O
-
-
-
?
chloromethyl phenyl sulfide + NADPH + H+ + O2
chloromethyl phenyl (R)-sulfoxide + NADP+ + H2O
-
-
76% enantiomeric excess
-
?
cyclopropyl phenyl sulfide + NADPH + H+ + O2
cyclopropyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
97% enantiomeric excess
-
?
ethenyl phenyl sulfide + NADPH + H+ + O2
ethenyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
98% enantiomeric excess
-
?
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
isobutyrophenone + NADPH + H+ + O2
phenyl isobutyrate + NADP+ + H2O
-
-
-
?
methyl (phenylsulfanyl)methyl ether + NADPH + H+ + O2
methoxymethyl phenyl (R)-sulfoxide + NADP+ + H2O
-
-
98% enantiomeric excess
-
?
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
methyl 2-phenylethyl (R)-sulfoxide + NADP+ + H2O
-
-
51% enantiomeric excess
-
?
methyl 3-phenylpropyl sulfide + NADPH + H+ + O2
methyl 3-phenylpropyl (R)-sulfoxide + NADP+ + H2O
-
-
57% enantiomeric excess
-
?
methyl 4-tolyl sulfide + NADPH + H+ + O2
?
-
enantioselectivity, HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxide
-
?
methyl naphthalen-2-yl sulfide + NADPH + H+ + O2
methyl naphthalen-2-yl (S)-sulfoxide + NADP+ + H2O
-
-
95% enantiomeric excess
-
?
methyl-4-tolyl sulfide + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
methylphenyl sulfide + NADPH + H+ + O2
?
-
enantioselectivity, HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxide
-
?
phenyl prop-2-en-1-yl sulfide + NADPH + H+ + O2
phenyl prop-2-en-1-yl (S)-sulfoxide + NADP+ + H2O
-
-
98% enantiomeric excess
-
?
phenyl propyl sulfide + NADPH + H+ + O2
phenyl propyl (S)-sulfoxide + NADP+ + H2O
-
-
97% enantiomeric excess
-
?
phenylacetone + NADPH + H+ + O2
benzyl acetate + NADP+ + H2O
-
reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
propiophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
propiophenone + NADPH + H+ + O2
phenyl propionate + NADP+ + H2O
-
-
-
?
thioanisole + NADPH + H+ + O2
methyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
thioanisole + NADPH + H+ + O2
methyl phenyl sulfoxide + NADP+ + H2O
-
-
-
-
?
trifluoroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
Baeyer-Villiger oxidation, stereospecific reaction, regioselectivity
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
1 unit enzyme oxidizes 1 micromol substrate to product per minute at pH 9.0, 25°C in the presence of NADPH
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
Baeyer-Villiger oxidation, stereospecific reaction, regioselectivity
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
1 unit enzyme oxidizes 1 micromol substrate to product per minute at pH 9.0, 25°C in the presence of NADPH
-
-
?
1-indanone + NADPH + H+ + O2
3,4-dihydrocoumarin + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h 26% conversion without cosolvent, with 5% 2-octanole 39% conversion, with 5% hexane 44% conversion, conversion with 5% hexane at pH 8.0 is 39%, at pH 9.0 44%, at pH 10.0 47%, at pH 10.5 21%
-
?
1-indanone + NADPH + H+ + O2
3,4-dihydrocoumarin + NADP+ + H2O
-
substrate is only accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
1-indanone + NADPH + H+ + O2
3,4-dihydrocoumarin + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h 26% conversion without cosolvent, with 5% 2-octanole 39% conversion, with 5% hexane 44% conversion, conversion with 5% hexane at pH 8.0 is 39%, at pH 9.0 44%, at pH 10.0 47%, at pH 10.5 21%
-
?
1-tetralone + NADPH + H+ + O2
4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 96 h only 5% of the expected product conversion without cosolvent, with 5% tBuOMe 7% conversion, with 5% toluene 26% conversion, with 5% 2-octanol 25% conversion, with 5% hexane 15% conversion
-
?
1-tetralone + NADPH + H+ + O2
4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O
-
substrate is accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
1-tetralone + NADPH + H+ + O2
4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 96 h only 5% of the expected product conversion without cosolvent, with 5% tBuOMe 7% conversion, with 5% toluene 26% conversion, with 5% 2-octanol 25% conversion, with 5% hexane 15% conversion
-
?
2'-hydroxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
2'-hydroxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
2-chloro-thioanisole + NADPH + H+ + O2
2-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
2-chloro-thioanisole + NADPH + H+ + O2
2-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
2-hydroxyacetophenone + NADPH + H+ + O2
2-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
2-hydroxyacetophenone + NADPH + H+ + O2
2-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
2-hydroxyacetophenone + NADPH + H+ + O2
2-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
2-indanone + NADPH + H+ + O2
3-isochromanone + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h no product without cosolvent, only with 5% hexane or 5% CH2Cl2 10% conversion
-
?
2-indanone + NADPH + H+ + O2
3-isochromanone + NADP+ + H2O
50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH
after 72 h no product without cosolvent, only with 5% hexane or 5% CH2Cl2 10% conversion
-
?
3-chloro-thioanisole + NADPH + H+ + O2
3-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
3-chloro-thioanisole + NADPH + H+ + O2
3-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-amino-thioanisole + NADPH + H+ + O2
4-aminophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-amino-thioanisole + NADPH + H+ + O2
4-aminophenyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
4-aminoacetophenone + NADPH + H+ + O2
1-(4-aminophenyl)ethanol + NADP+ + H2O
-
-
-
?
4-aminoacetophenone + NADPH + H+ + O2
1-(4-aminophenyl)ethanol + NADP+ + H2O
-
best substrate
-
?
4-aminoacetophenone + NADPH + H+ + O2
1-(4-aminophenyl)ethanol + NADP+ + H2O
strictly NADPH-dependent
-
?
4-aminoacetophenone + NADPH + H+ + O2
1-(4-aminophenyl)ethanol + NADP+ + H2O
-
-
-
?
4-fluoroacetophenone + NADPH + H+ + O2
4-fluorophenyl acetate + NADP+ + H2O
-
-
-
?
4-fluoroacetophenone + NADPH + H+ + O2
4-fluorophenyl acetate + NADP+ + H2O
-
-
-
?
4-fluoroacetophenone + NADPH + H+ + O2
4-fluorophenyl acetate + NADP+ + H2O
strictly NADPH-dependent, poor substrate
-
?
4-hydroxy-3-methylacetophenone + NADPH + H+ + O2
4-hydroxy-3-methylphenyl acetate + NADP+ + H2O
-
-
-
r
4-hydroxy-3-methylacetophenone + NADPH + H+ + O2
4-hydroxy-3-methylphenyl acetate + NADP+ + H2O
strictly NADPH-dependent
-
?
4-hydroxyacetophenone + NADH + H+ + O2
4-hydroxyphenyl acetate + NAD+ + H2O
-
700fold preference for NADPH over NADH
-
?
4-hydroxyacetophenone + NADH + H+ + O2
4-hydroxyphenyl acetate + NAD+ + H2O
-
700fold preference for NADPH over NADH
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
700fold preference for NADPH over NADH, Arg-440 plays an important role in catalysis
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
NADPH- and oxygen-dependent Baeyer-Villiger oxidation, good substrate
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
strictly NADPH-dependent, tight coupling between NADPH oxidation and substrate oxygenation
product is instable
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
physiological substrate
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
catalyzes the first step in the degradation of 4-hydroxyacetophenone
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
the enzyme catalyzes the first committed step in th 4-hydroxyacetophenone catabolism, pathway overview
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
enantiospecific reaction, overview
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
NADPH- and oxygen-dependent Baeyer-Villiger oxidation, good substrate
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
physiological substrate
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
700fold preference for NADPH over NADH, Arg-440 plays an important role in catalysis
-
?