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(4-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
(R)-2-phenylpentan-3-one + NADPH + H+ + O2
?
-
-
-
-
?
(R)-3-phenylbutan-2-one + NADPH + H+ + O2
?
-
-
-
-
?
(R)-3-phenylpentan-2-one + NADPH + H+ + O2
?
-
-
-
-
?
(R)-4-phenylhexan-2-one + NADPH + H+ + O2
?
-
-
-
-
?
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
-
-
?
1-indanone + NADPH + H+ + O2
3,4-dihydrocoumarin + NADP+ + H2O
1-tetralone + NADPH + H+ + O2
4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O
2'-hydroxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
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-acetylpyridine + NADPH + H+ + O2
?
-
-
-
?
2-acetylpyrrole + NADPH + H+ + O2
?
-
-
-
?
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-chloro-thioanisole + NADPH + H+ + O2
2-chlorophenyl methyl sulfoxide + NADP+ + H2O
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-hydroxyacetophenone + NADPH + H+ + O2
2-hydroxyphenyl acetate + NADP+ + H2O
2-indanone + NADPH + H+ + O2
3-isochromanone + NADP+ + H2O
2-oxabicyclo[3.2.0]heptan-6-one + NADPH + O2
?
2-oxabicyclo[4.2.0]octan-7-one + NADPH + O2
?
-
-
-
-
?
2-phenylpentan-3-one + NADPH + H+ + O2
?
-
-
-
-
?
2-phenylpropionaldehyde + NADPH + H+ + O2
?
-
-
-
-
?
2-phenylpropionaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
2-pyrrole carboxaldehyde + NADPH + H+ + O2
?
-
-
-
?
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-chloro-thioanisole + NADPH + H+ + O2
3-chlorophenyl methyl sulfoxide + NADP+ + H2O
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-oxabicyclo[3.2.0]heptan-6-one + NADPH + O2
?
-
-
-
-
?
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-aminophenyl methyl sulfoxide + NADP+ + H2O
4-amino-thioanisole + NADPH + H+ + O2
4-[(S)-methylsulfinyl]aniline + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
4-aminoacetophenone + NADPH + H+ + O2
1-(4-aminophenyl)ethanol + NADP+ + H2O
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
4-fluorophenyl acetate + NADP+ + H2O
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-hydroxyacetophenone + NADH + H+ + O2
4-hydroxyphenyl acetate + NAD+ + H2O
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
4-hydroxybenzaldehyde + NADPH + H+ + O2
4-hydroxybenzoate + NADP+ + H2O
4-hydroxybenzaldehyde + NADPH + H+ + O2
?
strictly NADPH-dependent
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
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
4-methoxyphenyl acetate + 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
4-methylphenyl acetate + NADP+ + H2O
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
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
acetylcyclohexane + NADPH + H+ + O2
?
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
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
bicyclo[3.2.0]heptan-6-one + NADPH + O2
?
-
-
-
-
?
bicyclo[4.2.0]octan-7-one + NADPH + O2
?
-
-
-
-
?
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
-
?
cyclohexane carboxaldehyde + NADPH + H+ + O2
?
-
-
-
?
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
-
?
hydroxyacetone + NADPH + H+ + O2
?
-
very poor substrate
-
?
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
-
-
-
?
rac-2-methyl-1-indanone + NADPH + H+ + O2
(R)-3-methyl-3,4-dihydrocoumarin + NADP+ + H2O
thioanisole + NADPH + H+ + O2
methyl phenyl (S)-sulfoxide + NADP+ + H2O
-
-
99% enantiomeric excess
-
?
thioanisole + NADPH + H+ + O2
methyl phenyl sulfoxide + NADP+ + H2O
-
-
-
-
?
tricyclo[4.2.1.02,5]nonan-3-one + NADPH + O2
?
-
-
-
-
?
trifluoroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
additional information
?
-
(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
-
?
2-oxabicyclo[3.2.0]heptan-6-one + NADPH + O2
?
-
-
-
-
?
2-oxabicyclo[3.2.0]heptan-6-one + NADPH + O2
?
-
-
-
-
?
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
-
?
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
catalyzes the first step in the degradation of 4-hydroxyacetophenone
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
-
-
?
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
-
consumption of one molecule of oxygen and oxidation of one molecule of NADPH per substrate molecule, specific for NADPH as electron donor, requirement for O2
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
involved in the Baeyer-Villiger oxygenation of 4-hydroxyacetophenone, catalyzes one of the steps in the catabolism of 4-ethylphenol, inducible enzyme
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
and related cyclic aliphatic ketones, no activity with NADH as cofactor
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
consumption of one molecule of oxygen and oxidation of one molecule of NADPH per substrate molecule, specific for NADPH as electron donor, requirement for O2
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
-
involved in the Baeyer-Villiger oxygenation of 4-hydroxyacetophenone, catalyzes one of the steps in the catabolism of 4-ethylphenol, inducible enzyme
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
and related cyclic aliphatic ketones, no activity with NADH as cofactor
-
-
?
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
50 mM Tris-HCl, pH 8.0, 30°C
-
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
4-hydroxybenzoate + NADP+ + H2O
-
-
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
4-hydroxybenzoate + NADP+ + H2O
-
-
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
-
-
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
-
good substrate
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
strictly NADPH-dependent
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
-
good substrate
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
-
-
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
strictly NADPH-dependent
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
-
specific for NADPH as electron donor, requirement for O2
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
-
specific for NADPH as electron donor, requirement for O2
-
?
4-methoxyacetophenone + NADPH + H+ + O2
4-methoxyphenyl acetate + NADP+ + H2O
-
-
-
?
4-methoxyacetophenone + NADPH + H+ + O2
4-methoxyphenyl acetate + NADP+ + H2O
-
-
-
?
4-methoxyacetophenone + NADPH + H+ + O2
4-methoxyphenyl acetate + NADP+ + H2O
strictly NADPH-dependent
-
?
4-methoxyacetophenone + NADPH + H+ + O2
4-methoxyphenyl acetate + NADP+ + H2O
-
-
-
?
4-methoxyacetophenone + NADPH + H+ + O2
4-methoxyphenyl acetate + NADP+ + H2O
-
-
-
?
4-methylacetophenone + NADPH + H+ + O2
4-methylphenyl acetate + NADP+ + H2O
-
-
-
?
4-methylacetophenone + NADPH + H+ + O2
4-methylphenyl acetate + NADP+ + H2O
-
-
-
?
4-methylacetophenone + NADPH + H+ + O2
4-methylphenyl acetate + NADP+ + H2O
strictly NADPH-dependent
-
?
4-methylacetophenone + NADPH + H+ + O2
4-methylphenyl acetate + NADP+ + H2O
-
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
-
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
-
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
strictly NADPH-dependent
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
-
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
-
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
strictly NADPH-dependent
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
-
specific for NADPH as electron donor, requirement for O2
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
-
specific for NADPH as electron donor, requirement for O2
-
?
acetylcyclohexane + NADPH + H+ + O2
?
-
-
-
?
acetylcyclohexane + NADPH + H+ + O2
?
-
poor substrate
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
-
-
-
-
?
rac-2-methyl-1-indanone + NADPH + H+ + O2
(R)-3-methyl-3,4-dihydrocoumarin + NADP+ + H2O
-
low conversion and selectivity
-
-
?
rac-2-methyl-1-indanone + NADPH + H+ + O2
(R)-3-methyl-3,4-dihydrocoumarin + NADP+ + H2O
-
low conversion and selectivity
-
-
?
additional information
?
-
-
a broad range of carbonylic compounds that are structurally more or less similar to 4-hydroxyacetophenone are substrates, catalyzes Baeyer-Villiger reaction with aromatic ketones and aldehydes, enzyme is capable of enantioselective formation of lactones from ketones and is also able to catalyze stereoselective sulfoxidation reactions by using aromatic sulfides, enantioselectivity, not: 2-nitroacetophenone, 4-nitroacetophenone, benzophenone, benzoin, 2-acetonaphthone, 3-acetylpyridine, benzoic acid, methyl 4-hydroxybenzoate, benzamide, N,N-dimethylaniline, phenylacetone, 1-indanone, 4-hydroxy-1-indanone, 1,3-indanone, 4-chromanone, cyclopentanone, cyclohexanone, progesterone, dihydrocarvone, acetone, butanone, 4-heptanone
-
?
additional information
?
-
-
catalyzes Baeyer-Villiger oxidation reactions on various ketones, oxidizes a variety of aromatic ketones and sulfides
-
?
additional information
?
-
-
catalyzes the Baeyer-Villiger oxidation of aromatic compounds, converts a wide range of acetophenones via a Baeyer-Villiger rearrangement reaction into the corresponding phenyl acetates, the highest catalytic efficiency is observed 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 forming hydrogen peroxide, not: cyclohexanone, cyclopentanone, NADH
-
?
additional information
?
-
catalyzes the Baeyer-Villiger oxidation of aromatic compounds, converts a wide range of acetophenones via a Baeyer-Villiger rearrangement reaction into the corresponding phenyl acetates, the highest catalytic efficiency is observed 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 forming hydrogen peroxide, not: cyclohexanone, cyclopentanone, NADH
-
?
additional information
?
-
-
substrate specificity, regioselectivity, the enzyme preferably and stereospecifically catalyzes Baeyer-Villiger oxidations of of ketones bearing a cyclobutanone structural motif, e.g. oxidation of several prochiral cyclobutanones to antipodal butyrolactones, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes Baeyer-Villiger oxidations of a wide range of ketones, thereby generating esters or lactones, overview
-
-
?
additional information
?
-
-
the recombinant enzyme is highly enantioselective in the synthesis of chiral phenyl and benzyl sulfoxides, oxidation of aromatic sulfides, substrate specificity and enantioselectivity, overview
-
-
?
additional information
?
-
-
a Bayer-Villinger monooxygenase, substrate specificity with several racemic cyclic and linear ketones, as well as 2-phenylpropionaldehyde, high enantioselectivites can be obtained in the kinetic resolution processes depending on the substrate structure and the reaction conditions, overview
-
-
?
additional information
?
-
the enzyme is active with a wide range of aromatic and aliphatic ketones
-
-
?
additional information
?
-
-
the enzyme is active with a wide range of aromatic and aliphatic ketones
-
-
?
additional information
?
-
no reaction with 2-tetralone or 4-methoxy-1-indanone as substrate, no effect of changed conditions (pH, temperature, organic cosolvents)
-
-
?
additional information
?
-
-
no activity with a racemic 2-methyl-1-tetralone
-
-
?
additional information
?
-
-
a broad range of carbonylic compounds that are structurally more or less similar to 4-hydroxyacetophenone are substrates, catalyzes Baeyer-Villiger reaction with aromatic ketones and aldehydes, enzyme is capable of enantioselective formation of lactones from ketones and is also able to catalyze stereoselective sulfoxidation reactions by using aromatic sulfides, enantioselectivity, not: 2-nitroacetophenone, 4-nitroacetophenone, benzophenone, benzoin, 2-acetonaphthone, 3-acetylpyridine, benzoic acid, methyl 4-hydroxybenzoate, benzamide, N,N-dimethylaniline, phenylacetone, 1-indanone, 4-hydroxy-1-indanone, 1,3-indanone, 4-chromanone, cyclopentanone, cyclohexanone, progesterone, dihydrocarvone, acetone, butanone, 4-heptanone
-
?
additional information
?
-
-
catalyzes Baeyer-Villiger oxidation reactions on various ketones, oxidizes a variety of aromatic ketones and sulfides
-
?
additional information
?
-
-
substrate specificity, regioselectivity, the enzyme preferably and stereospecifically catalyzes Baeyer-Villiger oxidations of of ketones bearing a cyclobutanone structural motif, e.g. oxidation of several prochiral cyclobutanones to antipodal butyrolactones, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes Baeyer-Villiger oxidations of a wide range of ketones, thereby generating esters or lactones, overview
-
-
?
additional information
?
-
-
the recombinant enzyme is highly enantioselective in the synthesis of chiral phenyl and benzyl sulfoxides, oxidation of aromatic sulfides, substrate specificity and enantioselectivity, overview
-
-
?
additional information
?
-
-
no activity with a racemic 2-methyl-1-tetralone
-
-
?
additional information
?
-
-
catalyzes the Baeyer-Villiger oxidation of aromatic compounds, converts a wide range of acetophenones via a Baeyer-Villiger rearrangement reaction into the corresponding phenyl acetates, the highest catalytic efficiency is observed 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 forming hydrogen peroxide, not: cyclohexanone, cyclopentanone, NADH
-
?
additional information
?
-
catalyzes the Baeyer-Villiger oxidation of aromatic compounds, converts a wide range of acetophenones via a Baeyer-Villiger rearrangement reaction into the corresponding phenyl acetates, the highest catalytic efficiency is observed 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 forming hydrogen peroxide, not: cyclohexanone, cyclopentanone, NADH
-
?
additional information
?
-
no reaction with 2-tetralone or 4-methoxy-1-indanone as substrate, no effect of changed conditions (pH, temperature, organic cosolvents)
-
-
?
additional information
?
-
the enzyme is active with a wide range of aromatic and aliphatic ketones
-
-
?
additional information
?
-
-
the enzyme is active with a wide range of aromatic and aliphatic ketones
-
-
?
additional information
?
-
-
not: benzophenone, cyclohexylacetone, NADH
-
?
additional information
?
-
-
not: benzophenone, cyclohexylacetone, NADH
-
?
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