1.14.13.84: 4-hydroxyacetophenone monooxygenase

This is an abbreviated version!
For detailed information about 4-hydroxyacetophenone monooxygenase, go to the full flat file.

Word Map on EC 1.14.13.84

Reaction

(4-hydroxyphenyl)ethan-1-one
+
NADPH
+
H+
+
O2
=
4-hydroxyphenyl acetate
+
NADP+
+
H2O

Synonyms

4-hydroxyacetophenone monooxygenase, arylketone monooxygenase, Baeyer-Villiger monooxygenase, hAPA, HAPMO, More, oxygenase, 4-hydroxyacetophenone mono-

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.13.84 4-hydroxyacetophenone monooxygenase

Substrates Products

Substrates Products on EC 1.14.13.84 - 4-hydroxyacetophenone monooxygenase

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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-hydroxyphenyl)ethan-1-one + NADPH + O2
4-hydroxyphenyl acetate + NADP+ + H2O
show the reaction diagram
(R)-2-phenylpentan-3-one + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
(R)-3-phenylbutan-2-one + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
(R)-3-phenylpentan-2-one + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
(R)-4-phenylhexan-2-one + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
1-bromo-indanone + NADPH + H+ + O2
6-bromoisochroman-1-one + NADP+ + H2O
show the reaction diagram
-
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
show the reaction diagram
1-tetralone + NADPH + H+ + O2
4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O
show the reaction diagram
2'-hydroxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
2,4-pentanedione + NADPH + H+ + O2
?
show the reaction diagram
-
very poor substrate
-
?
2,4-pentanedione + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
2-acetylpyridine + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
2-acetylpyrrole + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
2-acetylpyrrole + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
2-chloro-thioanisole + NADPH + H+ + O2
2-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
96% enantiomeric excess
-
?
2-chloro-thioanisole + NADPH + H+ + O2
2-chlorophenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
2-chloroethyl phenyl sulfide + NADPH + H+ + O2
2-chloroethyl phenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
81% enantiomeric excess
-
?
2-decanone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
2-hydroxyacetophenone + NADPH + H+ + O2
2-hydroxyphenyl acetate + NADP+ + H2O
show the reaction diagram
2-indanone + NADPH + H+ + O2
3-isochromanone + NADP+ + H2O
show the reaction diagram
2-oxabicyclo[3.2.0]heptan-6-one + NADPH + O2
?
show the reaction diagram
2-oxabicyclo[4.2.0]octan-7-one + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
2-phenylpentan-3-one + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
2-phenylpropionaldehyde + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
2-phenylpropionaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
2-pyrrole carboxaldehyde + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
3'-hydroxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
3-aminoacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
3-chloro-2-butanone + NADPH + H+ + O2
?
show the reaction diagram
-
very poor substrate
-
?
3-chloro-thioanisole + NADPH + H+ + O2
3-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
99% enantiomeric excess
-
?
3-chloro-thioanisole + NADPH + H+ + O2
3-chlorophenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
3-hydroxyacetophenone + NADPH + H+ + O2
3-hydroxyphenyl acetate + NADP+ + H2O
show the reaction diagram
-
-
-
?
3-methoxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
3-nitroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
3-oxabicyclo[3.2.0]heptan-6-one + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
3-phenyl-2-butanone + NADPH + H+ + O2
1-phenylethyl acetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
3-phenyl-2-pentanone + NADPH + H+ + O2
1-phenylpropyl acetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
4-acetylpyridine + NADPH + H+ + O2
?
show the reaction diagram
-
very poor substrate
-
?
4-amino-thioanisole + NADPH + H+ + O2
4-aminophenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
4-amino-thioanisole + NADPH + H+ + O2
4-[(S)-methylsulfinyl]aniline + NADP+ + H2O
show the reaction diagram
-
-
99% enantiomeric excess
-
?
4-aminoacetophenone + NADPH + H+ + O2
1-(4-aminophenyl)ethanol + NADP+ + H2O
show the reaction diagram
4-aminoacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
4-chloro-thioanisole + NADPH + H+ + O2
4-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
96% enantiomeric excess
-
?
4-chloro-thioanisole + NADPH + H+ + O2
4-chlorophenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-chloroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
4-cyano-thioanisole + NADPH + H+ + O2
4-cyanophenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-cyano-thioanisole + NADPH + H+ + O2
4-[(S)-methylsulfinyl]benzonitrile + NADP+ + H2O
show the reaction diagram
-
-
96% enantiomeric excess
-
?
4-fluoroacetophenone + NADPH + H+ + O2
4-fluorophenyl acetate + NADP+ + H2O
show the reaction diagram
4-fluoroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
4-hydroxy-2-decanone + NADPH + H+ + O2
4-hydroxyoctyl acetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
4-hydroxy-2-nonanone + NADPH + H+ + O2
4-hydroxyheptylacetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
4-hydroxy-2-octanone + NADPH + H+ + O2
4-hydroxyhexyl acetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
4-hydroxy-2-undecanone + NADPH + H+ + O2
4-hydroxynonyl acetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
4-hydroxy-3-methylacetophenone + NADPH + H+ + O2
4-hydroxy-3-methylphenyl acetate + NADP+ + H2O
show the reaction diagram
4-hydroxy-4-phenyl-2-butanone + NADPH + H+ + O2
1-hydroxy-1-phenylethyl acetate + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 25C
-
-
?
4-hydroxyacetophenone + NADH + H+ + O2
4-hydroxyphenyl acetate + NAD+ + H2O
show the reaction diagram
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
show the reaction diagram
4-hydroxybenzaldehyde + NADPH + H+ + O2
4-hydroxybenzoate + NADP+ + H2O
show the reaction diagram
4-hydroxybenzaldehyde + NADPH + H+ + O2
?
show the reaction diagram
strictly NADPH-dependent
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
4-hydroxyphenyl propionate + NADP+ + H2O
show the reaction diagram
4-methoxy-thioanisole + NADPH + H+ + O2
4-methoxyphenyl methyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
99% enantiomeric excess
-
?
4-methoxy-thioanisole + NADPH + H+ + O2
4-methoxyphenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-methoxyacetophenone + NADPH + H+ + O2
4-methoxyphenyl acetate + NADP+ + H2O
show the reaction diagram
4-methoxyacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
4-methyl-thioanisole + NADPH + H+ + O2
4-methylphenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-methyl-thioanisole + NADPH + H+ + O2
methyl 4-methylphenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
99% enantiomeric excess
-
?
4-methylacetophenone + NADPH + H+ + O2
4-methylphenyl acetate + NADP+ + H2O
show the reaction diagram
4-methylacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
4-nitro-thioanisole + NADPH + H+ + O2
4-nitrophenyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-nitro-thioanisole + NADPH + H+ + O2
methyl 4-nitrophenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
87% enantiomeric excess
-
?
4-nitroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
5-bromo-1-indanone + NADPH + H+ + O2
5-bromo-3,4-dihydrochromen-2-one + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 9.0, 20C, 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
show the reaction diagram
50 mM Tris-HCl, pH 9.0, 20C, 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
show the reaction diagram
50 mM Tris-HCl, pH 9.0, 20C, 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
show the reaction diagram
50 mM Tris-HCl, pH 9.0, 20C, 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
show the reaction diagram
50 mM Tris-HCl, pH 9.0, 20C, 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
show the reaction diagram
-
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
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
acetophenone + NADPH + H+ + O2
phenyl acetate + NADP+ + H2O
show the reaction diagram
acetylcyclohexane + NADPH + H+ + O2
?
show the reaction diagram
benzaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
benzaldehyde + NADPH + H+ + O2
phenyl formate + NADP+ + H2O
show the reaction diagram
-
-
-
?
benzocyclobutanone + NADPH + H+ + O2
2-coumaranone + NADP+ + H2O
show the reaction diagram
-
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
show the reaction diagram
50 mM Tris-HCl, pH 9.0, 20C, 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
show the reaction diagram
-
-
82% enantiomeric excess
-
?
benzyl butyl sulfide + NADPH + H+ + O2
benzyl butyl (R)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
77% enantiomeric excess
-
?
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
81% enantiomeric excess
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
85% enantiomeric excess
-
?
benzyl propyl sulfide + NADPH + H+ + O2
benzyl propyl (R)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
65% enantiomeric excess
-
?
bicyclohept-2-en-6-one + NADPH + H+ + O2
?
show the reaction diagram
-
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
?
show the reaction diagram
bicyclo[3.2.0]heptan-6-one + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
bicyclo[4.2.0]octan-7-one + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
butyl phenyl sulfide + NADPH + H+ + O2
butyl phenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
71% enantiomeric excess
-
?
butyrophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
butyrophenone + NADPH + H+ + O2
phenyl butyrate + NADP+ + H2O
show the reaction diagram
-
-
-
?
chloromethyl phenyl sulfide + NADPH + H+ + O2
chloromethyl phenyl (R)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
76% enantiomeric excess
-
?
cyclohexane carboxaldehyde + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
cyclopropyl phenyl sulfide + NADPH + H+ + O2
cyclopropyl phenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
97% enantiomeric excess
-
?
ethenyl phenyl sulfide + NADPH + H+ + O2
ethenyl phenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
98% enantiomeric excess
-
?
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
99% enantiomeric excess
-
?
hydroxyacetone + NADPH + H+ + O2
?
show the reaction diagram
-
very poor substrate
-
?
isobutyrophenone + NADPH + H+ + O2
phenyl isobutyrate + NADP+ + H2O
show the reaction diagram
-
-
-
?
methyl (phenylsulfanyl)methyl ether + NADPH + H+ + O2
methoxymethyl phenyl (R)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
98% enantiomeric excess
-
?
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
methyl 2-phenylethyl (R)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
51% enantiomeric excess
-
?
methyl 3-phenylpropyl sulfide + NADPH + H+ + O2
methyl 3-phenylpropyl (R)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
57% enantiomeric excess
-
?
methyl 4-tolyl sulfide + NADPH + H+ + O2
?
show the reaction diagram
-
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
show the reaction diagram
-
-
95% enantiomeric excess
-
?
methyl-4-tolyl sulfide + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
methylphenyl sulfide + NADPH + H+ + O2
?
show the reaction diagram
-
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
show the reaction diagram
-
-
98% enantiomeric excess
-
?
phenyl propyl sulfide + NADPH + H+ + O2
phenyl propyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
97% enantiomeric excess
-
?
phenylacetone + NADPH + H+ + O2
benzyl acetate + NADP+ + H2O
show the reaction diagram
-
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
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
propiophenone + NADPH + H+ + O2
phenyl propionate + NADP+ + H2O
show the reaction diagram
-
-
-
?
rac-2-methyl-1-indanone + NADPH + H+ + O2
(R)-3-methyl-3,4-dihydrocoumarin + NADP+ + H2O
show the reaction diagram
thioanisole + NADPH + H+ + O2
methyl phenyl (S)-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
99% enantiomeric excess
-
?
thioanisole + NADPH + H+ + O2
methyl phenyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
tricyclo[4.2.1.02,5]nonan-3-one + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
trifluoroacetophenone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
50 mM Tris-HCl, pH 8.0, 30C
-
-
?
additional information
?
-