Information on EC 1.14.13.84 - 4-hydroxyacetophenone monooxygenase

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The expected taxonomic range for this enzyme is: Pseudomonas

EC NUMBER
COMMENTARY hide
1.14.13.84
-
RECOMMENDED NAME
GeneOntology No.
4-hydroxyacetophenone monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Bayer-Villiger reaction
oxidation
redox reaction
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
4-hydroxyacetophenone degradation
-
-
Bisphenol degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
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).
CAS REGISTRY NUMBER
COMMENTARY hide
156621-13-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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
4-aminophenyl acetate + 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
strictly NADPH-dependent
-
?
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
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
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
4-hydroxyacetophenone + NADPH + H+ + O2
4-hydroxyphenyl acetate + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
-
flavin-containing enzyme
NADH
-
700fold preference for NADPH over NADH
NADPH
additional information
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-Aminopyridine adenine dinucleotide phosphate
-
cofactor analogue, tight binding to the wild-type enzyme and mutant R440A
acetyl-NADP+
-
0.5 mM, 35% inhibition
amino-NADP+
-
very effective inhibitor, 0.005 mM, 80% inhibition
hexane
-
enzyme activity is markedly reduced at concentrations of hexane below 5% and over 30%
additional information
-
not inhibited by NADP+
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
hexane
-
enzyme activity is highest at concentrations of hexane between 5% and 30%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.857 - 4.9
2,4-Pentanedione
1.2
2-acetylpyridine
-
pH 7.5, 30C
0.103 - 0.33
2-acetylpyrrole
0.953
2-decanone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.121 - 0.61
2-hydroxyacetophenone
21.24
2-phenylpropionaldehyde
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.41
2-pyrrole carboxaldehyde
-
pH 7.5, 30C
0.246
3'-hydroxyacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.287
3-aminoacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
2 - 3
3-chloro-2-butanone
-
pH 7.5, 30C
1.4
3-hydroxyacetophenone
-
pH 7.5, 30C
0.0885
3-methoxyacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.244
3-nitroacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
1.9
4-acetylpyridine
-
pH 7.5, 30C
0.003 - 0.0082
4-aminoacetophenone
0.14
4-chloroacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.208 - 1.04
4-fluoroacetophenone
0.38
4-hydroxy-3-methylacetophenone
pH 8, 30C
0.0092 - 0.047
4-hydroxyacetophenone
0.1 - 0.101
4-hydroxybenzaldehyde
0.0024 - 0.023
4-hydroxypropiophenone
0.199 - 0.541
4-methoxyacetophenone
0.16 - 0.241
4-methylacetophenone
0.313
4-Nitroacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.384 - 2.3
acetophenone
4.8
acetylcyclohexane
-
pH 7.5, 30C
0.257 - 1.6
benzaldehyde
3.3
bicyclohept-2-en-6-one
-
pH 7.5, 30C
2 - 30.75
butyrophenone
3
cyclohexane carboxaldehyde
-
pH 7.5, 30C
29
Hydroxyacetone
-
pH 7.5, 30C
0.54
isobutyrophenone
-
pH 7.5, 30C
0.37
methyl 4-tolyl sulfide
-
pH 7.5, 30C
18.85
methyl-4-tolyl sulfide
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
1.4
methylphenyl sulfide
-
pH 7.5, 30C
0.3 - 3
NADH
0.012 - 3
NADPH
0.0894 - 0.53
propiophenone
0.112
trifluoroacetophenone
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
additional information
additional information
-
kinetic resolution of the racemic carbonyl compounds, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
21.2
2'-hydroxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
-
2.1 - 3.5
2,4-Pentanedione
7.8
2-acetylpyridine
Pseudomonas fluorescens
-
pH 7.5, 30C
9.4 - 11.3
2-acetylpyrrole
4.2
2-decanone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
6.7
2-hydroxyacetophenone
Pseudomonas fluorescens
-
pH 7.5, 30C
8.7
2-phenylpropionaldehyde
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
8.6
2-pyrrole carboxaldehyde
Pseudomonas fluorescens
-
pH 7.5, 30C
8.1
3'-hydroxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
1
3-aminoacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
7.4
3-chloro-2-butanone
Pseudomonas fluorescens
-
pH 7.5, 30C
4.8
3-hydroxyacetophenone
Pseudomonas fluorescens
-
pH 7.5, 30C
0.4
3-methoxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
1.2
3-nitroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.5
4-acetylpyridine
Pseudomonas fluorescens
-
pH 7.5, 30C
8.2 - 12.7
4-aminoacetophenone
1.6
4-chloroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
0.6 - 1.3
4-fluoroacetophenone
5.4
4-hydroxy-3-methylacetophenone
Pseudomonas fluorescens
Q93TJ5
pH 8, 30C
9.8 - 12.6
4-hydroxyacetophenone
7.6
4-hydroxybenzaldehyde
10.6 - 11.9
4-hydroxypropiophenone
1.2 - 1.7
4-methoxyacetophenone
4.4 - 6.3
4-methylacetophenone
2.6
4-Nitroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
4.5 - 16.3
acetophenone
3.9
acetylcyclohexane
Pseudomonas fluorescens
-
pH 7.5, 30C
2.2
benzaldehyde
6.7
bicyclohept-2-en-6-one
Pseudomonas fluorescens
-
pH 7.5, 30C
1.2 - 4.9
butyrophenone
5
cyclohexane carboxaldehyde
Pseudomonas fluorescens
-
pH 7.5, 30C
4.1
Hydroxyacetone
Pseudomonas fluorescens
-
pH 7.5, 30C
2.5
isobutyrophenone
Pseudomonas fluorescens
-
pH 7.5, 30C
7.3
methyl 4-tolyl sulfide
Pseudomonas fluorescens
-
pH 7.5, 30C
20
methyl-4-tolyl sulfide
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
4.7
methylphenyl sulfide
Pseudomonas fluorescens
-
pH 7.5, 30C
0.19 - 5.1
NADH
0.1 - 10.1
NADPH
2.6 - 11
propiophenone
15.4
trifluoroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.7
2,4-Pentanedione
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
3304
110
2-acetylpyrrole
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
9710
4.4
2-decanone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
7438
176
2-hydroxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
1365
0.4
2-phenylpropionaldehyde
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
13979
32.7
3'-hydroxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
39150
3.3
3-aminoacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
39151
4.3
3-methoxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
39152
4.9
3-nitroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
13130
1450
4-aminoacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
9709
11
4-chloroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
6308
6.2
4-fluoroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
7565
257
4-hydroxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
1816
5.9
4-methoxyacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
8521
18.5
4-methylacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
7564
8.4
4-Nitroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
3181
41.6
acetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
982
8.1
benzaldehyde
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
146
0.2
butyrophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
7566
1.1
methyl-4-tolyl sulfide
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
39153
28.5
propiophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
4109
138
trifluoroacetophenone
Pseudomonas putida
B7T912
312 microM NADPH, 50 mM Tris-HCl, pH 8.0, 30C
22480
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.54
crude cell extract, decrease of NADPH, 50 mM Tris-HCl, pH 8.0, 312.5 NADPH, air saturated, 30C
7.5
Q-Sepharose purified, decrease of NADPH, 50 mM Tris-HCl, pH 8.0, 312.5 NADPH, air saturated, 30C
8.1
-
pH 8, 30C
23.2
Reactive Red purified, decrease of NADPH, 50 mM Tris-HCl, pH 8.0, 312.5 NADPH, air saturated, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8 - 9
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 9
maximum activity pH at 8.0, below pH 6.0 the activity is very low, acetate buffer (pH 4.0-5.5), phosphate buffer (pH 7.5-8.0), Tris-HCl (pH 7.5-9.0), 25, 30 min
6 - 10
-
effects of pH on enantioselectivity, overview
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70000
-
gel filtration
140000
gel filtration
145100
-
mutant R339A, dimeric structure, mass spectrometry; mutant R440A, dimeric structure, mass spectrometry
145200
-
wild-type enzyme, dimeric structure, mass spectrometry
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
monomer
octamer
additional information
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 35
highest thermal stability at 30C, at 35C after 30 min 47% activity is retained, at 40C less than 1%, pH 8.0, 50 mM Tris-HCl buffer
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
the association with the coenzyme NADPH is crucial for enzyme stability, 3-aminopyridine adenine dinucleotide phosphate highly stabilizes the inactive dimeric state of the enzyme
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overexpressing Escherichia coli cells are centrifuged, washed, disrupted with a French pressure cell, centrifuged, supernatant (crude extract) purified to homogeneity in 2 chromatographic steps with Q-Sepharose and Reactive Red
recombinant HAPMO
-
wild-type and mutant HAPMO
-
wild-type, 25fold, and recombinant HAPMO
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli TOP10; gene hapE, overexpression in Escherichia coli
-
gene hapE, expression of wild-type and mutant enzymes in Escherichia coli
-
gne hapA, encoded in the hapCDEFGHIBA gene cluster, DNA and amino acid sequence determination and analysis
hapE gene, expression in Escherichia coli TOP10
-
hapE, expression in Escherichia coli BL21(DE3)pLysS, sequence analysis
overexpressed in Escherichia coli
-
overexpression of recombinant enzyme in Escherichia coli BL21(DE3)pLysS
PCR-amplification, expression in Escherichia coli DH5alpha, JM109, BL21 (DE3), and Rosetta
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G490A
strictly conserved glycine, dramatic effect of mutation on binding and oxidation of NADPH
H61T
-
the H61T mutant is purified as apo-enzyme and mainly exists as a dimeric species, the binding of FAD to the enzyme restores the octameric conformation
K439A
-
mutant with 100fold decrease in catalytic efficiency with NADPH, mainly caused by increased Km, 4fold increased efficiency with NADH
K439F
-
mutant with higher activity with NADH compared to wild-type HAPMO
K439N
-
mutant with higher activity with NADH compared to wild-type HAPMO
K439P
-
mutant with higher activity with NADH compared to wild-type HAPMO
G490A
-
strictly conserved glycine, dramatic effect of mutation on binding and oxidation of NADPH
-
H61T
-
the H61T mutant is purified as apo-enzyme and mainly exists as a dimeric species, the binding of FAD to the enzyme restores the octameric conformation
-
K439A
-
mutant with 100fold decrease in catalytic efficiency with NADPH, mainly caused by increased Km, 4fold increased efficiency with NADH
-
K439F
-
mutant with higher activity with NADH compared to wild-type HAPMO
-
K439N
-
mutant with higher activity with NADH compared to wild-type HAPMO
-
R339A
-
mutant with largely decreased affinity for NADPH and decreased catalytic efficiency with NADH; site-directed mutagenesiss, the mutant shows decreased activity and affinity to NADPH compared to the wild-type enzyme, the mutant only weakly interacts with 3-aminopyridine adenine dinucleotide phosphate
-
R440A
-
site-directed mutagenesiss, inactive mutant, the mutant shows highly increased affinity to NADPH compared to the wild-type enzyme; totally inactive mutant, Arg-440 is crucial for completing the catalytic cycle
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
additional information
Show AA Sequence (375 entries)
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