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1.14.13.92: phenylacetone monooxygenase

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

Word Map on EC 1.14.13.92

Reaction

phenylacetone
+
NADPH
+
H+
+
O2
=
Benzyl acetate
+
NADP+
+
H2O

Synonyms

4-hydroxyacetophenone monooxygenase, Baeyer-Villiger monooxygenase, BVMO, EtaA, HAPMO, M-PAMO, More, PAMO, phenylacetone monooxygenase, Tf PAMO

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
                1.14.13.92 phenylacetone monooxygenase

Substrates Products

Substrates Products on EC 1.14.13.92 - phenylacetone 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
(2-methylphenyl)acetone + NADPH + O2
? + NADP+ + O2
show the reaction diagram
-
-
-
-
?
(2R,3S)-3-methyl-2-pentylcyclopentanone + NADPH + H+ + O2
?
show the reaction diagram
-
less than 5% conversion
-
-
?
(R)-1-acetoxy-phenylacetone + NADPH + O2
(R)-1-hydroxy-1-phenylacetone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(R)-2-acetoxyphenylacetonitrile + NADPH + H+ + O2
?
show the reaction diagram
-
enantioselective reaction
-
-
?
(R)-3-(4-bromophenyl)butan-2-one + NADPH + H+ + O2
?
show the reaction diagram
-
enantioselective reaction
-
-
?
(S)-1-(3-trifluoromethylphenyl)ethyl acetate + NADPH + H+ + O2
?
show the reaction diagram
-
enantioselective reaction
-
-
?
(S)-nicotine + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
1-bromo-indanone + NADPH + O2
6-bromoisochroman-1-one + NADP+ + H2O
show the reaction diagram
-
substrate was only accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction was performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
1-indanone + NADPH + H+ + O2
1-isochromanone + NADP+ + H2O
show the reaction diagram
-
reaction product is only synthesized by the mutant M446G of phenylacetone monooxygenase 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
-
substrate was only accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction was performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
1-tetralone + NADPH + O2
4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O
show the reaction diagram
-
substrate was accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction was performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
1-[3-(benzylselanyl)phenyl]ethanone + NADPH + H+ + O2
1-(3-(benzylseleninyl)phenyl)ethanone + NADP+ + H2O
show the reaction diagram
-
more than 99% conversion
-
-
?
1-[3-(methylselanyl)phenyl]ethanone + NADPH + H+ + O2
1-(3-(methylseleninyl)phenyl)ethanone + NADP+ + H2O
show the reaction diagram
-
76% conversion
-
-
?
1-[4-(benzylselanyl)phenyl]ethanone + NADPH + H+ + O2
1-(4-(benzylseleninyl)phenyl)ethanone + NADP+ + H2O
show the reaction diagram
-
more than 99% conversion
-
-
?
1-[4-(methylselanyl)phenyl]ethanone + NADPH + H+ + O2
1-(4-(methylseleninyl)phenyl)ethanone + NADP+ + H2O
show the reaction diagram
-
more than 99% conversion
-
-
?
2-benzylcyclopentanone + NADPH + H+ + O2
?
show the reaction diagram
-
about 10% conversion
-
-
?
2-decanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
2-decanone + NADPH + O2
methyl nonanoate + octyl acetate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-dodecanone + NADPH + O2
? + NADP+
show the reaction diagram
-
-
-
-
?
2-dodecanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
2-dodecanone + NADPH + O2
nonyl acetate + methyl decanoate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-heptanone + NADPH + O2
pentyl acetate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-hexanone + NADPH + O2
butyl acetate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-indanone + NADPH + H+ + O2
3-isochromanone + NADP+ + H2O
show the reaction diagram
-
substrate is only accepted by the mutant M446G of phenylacetone monooxygenase of Thermobifida fusca, reaction is performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
2-methylcyclohexanone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
no activity with wild-type PAMO, but low to increased activity with enzyme mutants
-
-
?
2-methylphenylcyclohexanone + NADPH + O2
7-benzyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
mutant P3 prefers the R-isomer
-
-
?
2-nonanone + NADPH + H+ + O2
?
show the reaction diagram
-
less than 40% conversion
-
-
?
2-nonanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
2-octanone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
2-octanone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
?
2-octanone + NADPH + H+ + O2
heptylacetate + NADP+ + H2O
show the reaction diagram
-
-
-
?
2-octanone + NADPH + O2
heptyl acetate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
very low activity with wild-type PAMO, significantly increased activity with enzyme mutant P253F/G254A/R258M/L443F
-
-
?
2-phenylcyclohexanone + NADPH + O2
7-phenyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
molecular modeling of the Criegee intermediate, the wild-type enzyme prefers the S-isomer, while mutants P1-P3 all prefer the R-isomer
-
-
?
2-phenylpropionaldehyde + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
2-undecanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
3-(3-trifluoromethylphenyl)butan-2-one + NADPH + H+ + O2
?
show the reaction diagram
-
enantioselective reaction
-
-
?
3-(4-chlorophenyl)cyclobutanone + NADPH + H+ + O2
?
show the reaction diagram
-
about 40% conversion
-
-
?
3-benzylcyclobutanone + NADPH + H+ + O2
?
show the reaction diagram
-
about 45% conversion
-
-
?
3-decanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
3-octanone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
3-octanone + NADPH + O2
ethyl hexanoate + pentyl propanoate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
3-phenyl-2-butanone + NADPH + H+ + O2
(R)-3-phenylbutan-2-one + (S)-1-phenyethyl acetate
show the reaction diagram
-
enantioselective reaction
-
-
?
3-phenylcyclobutanone + NADPH + H+ + O2
?
show the reaction diagram
-
about 70% conversion
-
-
?
3-phenylpenta-2,4-dione + NADPH + O2
(R)-phenylacetylcarbinol + NADP+ + H2O
show the reaction diagram
-
-
the product is a well-known precursor in the synthesis of ephedrine and pseudoephedrine
-
?
4-decanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
4-heptanone + NADPH + O2
propanyl butanoate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-hydroxyacetophenone + NADPH + O2
acetic acid 4-hydroxyphenyl ester + NADP+ + O2
show the reaction diagram
-
-
-
-
?
4-methylcyclohexanone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
no activity with wild-type PAMO, but low to increased activity with enzyme mutants
-
-
?
4-phenylcyclohexanone + NADPH + O2
4-phenyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
6-methoxy-1-indanone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
-
substrate was only accepted by phenylacetone monooxygenase of Pseudomonas fluorescens but not of Thermobifida fusca, reaction was performed in presence of 10 U glucose-6-phosphate dehydrogenase and glucose-6-phosphate to recover NADPH
-
-
?
alpha-acetylphenylacetonitrile + NADPH + H+ + O2
(R)-2-acetoxyphenylacetonitrile + NADP+ + H2O
show the reaction diagram
-
enantioselective reaction
enantiopure product formation
-
?
benzocyclobutanone + NADPH + O2
2-coumaranone + NADP+ + H2O
show the reaction diagram
benzylacetone + NADPH + O2
?
show the reaction diagram
-
low activity
-
-
?
benzylacetone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
bicyclohept-2-en-6-one + NADPH + O2
3-oxabicyclo[3.3.0]oct-6-en-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
bicyclohept-2-en-6-one + NADPH + O2
? + NADP+ + O2
show the reaction diagram
-
-
-
-
?
bicyclo[2.2.1]heptan-2-one + NADPH + H+ + O2
?
show the reaction diagram
-
about 5% conversion
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
cycloheptanone + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
no activity with wild-type PAMO, but low to increased activity with enzyme mutants
-
-
?
cyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
show the reaction diagram
cyclopentanone + NADPH + H+ + O2
5-valerolactone + NADP+ + H2O
show the reaction diagram
cyclopentanone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
diketone + NADPH + O2
(R)-1-acetoxy-phenylacetone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
ethionamide + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
ethionamide + NADPH + O2
? + NADP+ + O2
show the reaction diagram
-
-
-
-
?
methyl 4-tolylsulfide + NADPH + O2
? + NADP+ + O2
show the reaction diagram
-
-
-
-
?
methyl-p-tolylsulfide + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
N,N-dimethylbenzylamine + NADPH + O2
N,N-dimethylbenzylamine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
phenylacetone + NADPH + H+ + O2
benzyl acetate + NADP+ + H2O
show the reaction diagram
phenylacetone + NADPH + O2
benzyl acetate + NADP+ + H2O
show the reaction diagram
phenylboronic acid + NADPH + O2
?
show the reaction diagram
-
formation of phenol
-
-
?
rac-2-ethylcyclohexanone + NADPH + O2
benzyl acetate + NADP+ + H2O
show the reaction diagram
-
substrate is only accepted by mutants of phenylacetone monooxygenase, reaction is performed in presence of 2 U secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus and isopropanol to recover NADPH
-
-
?
rac-3-methyl-4-phenylbutan-2-one + NADH + H+ + O2
(2R)-1-phenylpropan-2-yl acetate + NAD+ + H2O
show the reaction diagram
-
enantioselective reaction by PAMO
-
-
?
rac-3-methyl-4-phenylbutan-2-one + NADPH + H+ + O2
(2R)-1-phenylpropan-2-yl acetate + NADP+ + H2O
show the reaction diagram
-
enantioselective reaction by PAMO
-
-
?
rac-bicyclo [3.2.0]hept-2-en-6-one + NADPH + O2
?
show the reaction diagram
-
activity and stereoselectivity of wild-type and mutant enzymes, overview
-
-
?
thioanisole + NADH + H+ + O2
thioanisole sulfoxide + NAD+ + H2O
show the reaction diagram
-
low activity, less enantioselective reaction
-
-
?
thioanisole + NADPH + H+ + O2
?
show the reaction diagram
thioanisole + NADPH + H+ + O2
methyl phenyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
thioanisole + NADPH + H+ + O2
thioanisole sulfoxide + NADP+ + H2O
show the reaction diagram
-
enantioselective reaction
mainly (R)-sulfoxide
-
?
additional information
?
-