Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 1.14.13.84 extracted from

  • Kamerbeek, N.M.; Olsthoorn, A.J.J.; Fraaije, M.W.; Janssen, D.B.
    Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase (2003), Appl. Environ. Microbiol., 69, 419-426.
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
additional information potential of HAPMO for biotechnological applications Pseudomonas fluorescens

Cloned(Commentary)

Cloned (Comment) Organism
hapE gene, expression in Escherichia coli TOP10 Pseudomonas fluorescens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0024
-
4-hydroxypropiophenone pH 7.5, 30°C Pseudomonas fluorescens
0.0082
-
4-aminoacetophenone pH 7.5, 30°C Pseudomonas fluorescens
0.0092
-
4-hydroxyacetophenone pH 7.5, 30°C, pH-dependent Pseudomonas fluorescens
0.1
-
4-hydroxybenzaldehyde pH 8, 30°C Pseudomonas fluorescens
0.16
-
4-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
0.33
-
2-acetylpyrrole pH 7.5, 30°C Pseudomonas fluorescens
0.37
-
methyl 4-tolyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
0.41
-
2-pyrrole carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
0.53
-
propiophenone pH 7.5, 30°C Pseudomonas fluorescens
0.54
-
isobutyrophenone pH 7.5, 30°C Pseudomonas fluorescens
0.54
-
4-methoxyacetophenone pH 8, 30°C Pseudomonas fluorescens
0.61
-
2-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1
-
4-fluoroacetophenone pH 8, 30°C Pseudomonas fluorescens
1.2
-
2-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
1.4
-
3-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.4
-
methylphenyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
1.6
-
benzaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.9
-
4-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
2
-
butyrophenone pH 7.5, 30°C Pseudomonas fluorescens
2 3 3-chloro-2-butanone pH 7.5, 30°C Pseudomonas fluorescens
2.3
-
acetophenone pH 7.5, 30°C Pseudomonas fluorescens
3
-
cyclohexane carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
3.3
-
bicyclohept-2-en-6-one pH 7.5, 30°C Pseudomonas fluorescens
4.8
-
acetylcyclohexane pH 7.5, 30°C Pseudomonas fluorescens
4.9
-
2,4-Pentanedione pH 7.5, 30°C Pseudomonas fluorescens
29
-
Hydroxyacetone pH 7.5, 30°C Pseudomonas fluorescens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4-hydroxyacetophenone + NADPH + H+ + O2 Pseudomonas fluorescens physiological substrate 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 Pseudomonas fluorescens ACB physiological substrate 4-hydroxyphenyl acetate + NADP+ + H2O
-
?

Organism

Organism UniProt Comment Textmining
Pseudomonas fluorescens
-
-
-
Pseudomonas fluorescens ACB
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant HAPMO Pseudomonas fluorescens

Reaction

Reaction Comment Organism Reaction ID
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O enantioselectivity Pseudomonas fluorescens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,4-pentanedione + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
?
2-acetylpyridine + NADPH + H+ + O2
-
Pseudomonas fluorescens ?
-
?
2-acetylpyrrole + NADPH + H+ + O2
-
Pseudomonas fluorescens ?
-
?
2-hydroxyacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 2-hydroxyphenyl acetate + NADP+ + H2O
-
?
2-pyrrole carboxaldehyde + NADPH + H+ + O2
-
Pseudomonas fluorescens ?
-
?
3-chloro-2-butanone + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
?
3-hydroxyacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 3-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-acetylpyridine + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
?
4-aminoacetophenone + NADPH + H+ + O2 best substrate Pseudomonas fluorescens 1-(4-aminophenyl)ethanol + NADP+ + H2O
-
?
4-fluoroacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-fluorophenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 NADPH- and oxygen-dependent Baeyer-Villiger oxidation, good substrate Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 physiological substrate Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 NADPH- and oxygen-dependent Baeyer-Villiger oxidation, good substrate Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 physiological substrate Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-hydroxybenzoate + NADP+ + H2O
-
?
4-hydroxypropiophenone + NADPH + H+ + O2 good substrate Pseudomonas fluorescens 4-hydroxyphenyl propionate + NADP+ + H2O
-
?
4-hydroxypropiophenone + NADPH + H+ + O2 good substrate Pseudomonas fluorescens ACB 4-hydroxyphenyl propionate + NADP+ + H2O
-
?
4-methoxyacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methoxyphenyl acetate + NADP+ + H2O
-
?
4-methylacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methylphenyl acetate + NADP+ + H2O
-
?
acetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl acetate + NADP+ + H2O
-
?
acetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB phenyl acetate + NADP+ + H2O
-
?
acetylcyclohexane + NADPH + H+ + O2
-
Pseudomonas fluorescens ?
-
?
acetylcyclohexane + NADPH + H+ + O2 poor substrate Pseudomonas fluorescens ?
-
?
benzaldehyde + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl formate + NADP+ + H2O
-
?
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 Pseudomonas fluorescens ?
-
?
butyrophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl butyrate + NADP+ + H2O
-
?
cyclohexane carboxaldehyde + NADPH + H+ + O2
-
Pseudomonas fluorescens ?
-
?
hydroxyacetone + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
?
isobutyrophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl isobutyrate + NADP+ + H2O
-
?
methyl 4-tolyl sulfide + NADPH + H+ + O2 enantioselectivity, HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxide Pseudomonas fluorescens ?
-
?
methylphenyl sulfide + NADPH + H+ + O2 enantioselectivity, HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxide Pseudomonas fluorescens ?
-
?
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 Pseudomonas fluorescens ?
-
?
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 Pseudomonas fluorescens ACB ?
-
?
propiophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl propionate + NADP+ + H2O
-
?

Synonyms

Synonyms Comment Organism
HAPMO
-
Pseudomonas fluorescens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Pseudomonas fluorescens

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.5
-
4-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
0.6
-
4-fluoroacetophenone pH 8, 30°C Pseudomonas fluorescens
1.2
-
butyrophenone pH 7.5, 30°C Pseudomonas fluorescens
1.7
-
4-methoxyacetophenone pH 8, 30°C Pseudomonas fluorescens
2.1
-
2,4-Pentanedione pH 7.5, 30°C Pseudomonas fluorescens
2.2
-
benzaldehyde pH 7.5, 30°C Pseudomonas fluorescens
2.5
-
isobutyrophenone pH 7.5, 30°C Pseudomonas fluorescens
3.9
-
acetylcyclohexane pH 7.5, 30°C Pseudomonas fluorescens
4.1
-
Hydroxyacetone pH 7.5, 30°C Pseudomonas fluorescens
4.7
-
methylphenyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
4.8
-
3-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
5
-
cyclohexane carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
6.3
-
4-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
6.7
-
2-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
6.7
-
bicyclohept-2-en-6-one pH 7.5, 30°C Pseudomonas fluorescens
7.3
-
methyl 4-tolyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
7.4
-
3-chloro-2-butanone pH 7.5, 30°C Pseudomonas fluorescens
7.6
-
4-hydroxybenzaldehyde pH 8, 30°C Pseudomonas fluorescens
7.8
-
2-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
8.6
-
2-pyrrole carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
9.4
-
2-acetylpyrrole pH 7.5, 30°C Pseudomonas fluorescens
11
-
propiophenone pH 7.5, 30°C Pseudomonas fluorescens
11.9
-
4-hydroxypropiophenone pH 7.5, 30°C Pseudomonas fluorescens
12.6
-
4-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
12.7
-
4-aminoacetophenone pH 7.5, 30°C Pseudomonas fluorescens
13.2
-
acetophenone pH 7.5, 30°C Pseudomonas fluorescens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Pseudomonas fluorescens

Cofactor

Cofactor Comment Organism Structure
flavin flavin-containing enzyme Pseudomonas fluorescens
NADPH NADPH-dependent Pseudomonas fluorescens