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Literature summary 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

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

Cloned(Commentary)

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

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.13.84 0.0024
-
 4-hydroxypropiophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.0082
-
 4-aminoacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.0092
-
 4-hydroxyacetophenone pH 7.5, 30°C, pH-dependent Pseudomonas fluorescens
1.14.13.84 0.1
-
 4-hydroxybenzaldehyde pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 0.16
-
 4-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 0.33
-
 2-acetylpyrrole pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.37
-
 methyl 4-tolyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.41
-
 2-pyrrole carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.53
-
 propiophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.54
-
 isobutyrophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.54
-
 4-methoxyacetophenone pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 0.61
-
 2-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 1
-
 4-fluoroacetophenone pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 1.2
-
 2-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 1.4
-
 3-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 1.4
-
 methylphenyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 1.6
-
 benzaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 1.9
-
 4-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 2
-
 butyrophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 2 3 3-chloro-2-butanone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 2.3
-
 acetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 3
-
 cyclohexane carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 3.3
-
 bicyclohept-2-en-6-one pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 4.8
-
 acetylcyclohexane pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 4.9
-
 2,4-Pentanedione pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 29
-
 Hydroxyacetone pH 7.5, 30°C Pseudomonas fluorescens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.13.84 4-hydroxyacetophenone + NADPH + H+ + O2 Pseudomonas fluorescens physiological substrate 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxyacetophenone + NADPH + H+ + O2 Pseudomonas fluorescens ACB physiological substrate 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.84 Pseudomonas fluorescens
-
-
-
1.14.13.84 Pseudomonas fluorescens ACB
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.13.84 recombinant HAPMO Pseudomonas fluorescens

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O enantioselectivity Pseudomonas fluorescens
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.84 2,4-pentanedione + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
 ?
1.14.13.84 2-acetylpyridine + NADPH + H+ + O2
-
 Pseudomonas fluorescens ?
-
 ?
1.14.13.84 2-acetylpyrrole + NADPH + H+ + O2
-
 Pseudomonas fluorescens ?
-
 ?
1.14.13.84 2-hydroxyacetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens 2-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 2-pyrrole carboxaldehyde + NADPH + H+ + O2
-
 Pseudomonas fluorescens ?
-
 ?
1.14.13.84 3-chloro-2-butanone + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
 ?
1.14.13.84 3-hydroxyacetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens 3-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-acetylpyridine + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
 ?
1.14.13.84 4-aminoacetophenone + NADPH + H+ + O2 best substrate Pseudomonas fluorescens 1-(4-aminophenyl)ethanol + NADP+ + H2O
-
 ?
1.14.13.84 4-fluoroacetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-fluorophenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxyacetophenone + NADPH + H+ + O2 NADPH- and oxygen-dependent Baeyer-Villiger oxidation, good substrate Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxyacetophenone + NADPH + H+ + O2 physiological substrate Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxyacetophenone + NADPH + H+ + O2 NADPH- and oxygen-dependent Baeyer-Villiger oxidation, good substrate Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxyacetophenone + NADPH + H+ + O2 physiological substrate Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxybenzaldehyde + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-hydroxybenzoate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxypropiophenone + NADPH + H+ + O2 good substrate Pseudomonas fluorescens 4-hydroxyphenyl propionate + NADP+ + H2O
-
 ?
1.14.13.84 4-hydroxypropiophenone + NADPH + H+ + O2 good substrate Pseudomonas fluorescens ACB 4-hydroxyphenyl propionate + NADP+ + H2O
-
 ?
1.14.13.84 4-methoxyacetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-methoxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 4-methylacetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-methylphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 acetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 acetophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens ACB phenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 acetylcyclohexane + NADPH + H+ + O2
-
 Pseudomonas fluorescens ?
-
 ?
1.14.13.84 acetylcyclohexane + NADPH + H+ + O2 poor substrate Pseudomonas fluorescens ?
-
 ?
1.14.13.84 benzaldehyde + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl formate + NADP+ + H2O
-
 ?
1.14.13.84 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 ?
-
 ?
1.14.13.84 butyrophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl butyrate + NADP+ + H2O
-
 ?
1.14.13.84 cyclohexane carboxaldehyde + NADPH + H+ + O2
-
 Pseudomonas fluorescens ?
-
 ?
1.14.13.84 hydroxyacetone + NADPH + H+ + O2 very poor substrate Pseudomonas fluorescens ?
-
 ?
1.14.13.84 isobutyrophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl isobutyrate + NADP+ + H2O
-
 ?
1.14.13.84 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 ?
-
 ?
1.14.13.84 methylphenyl sulfide + NADPH + H+ + O2 enantioselectivity, HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxide Pseudomonas fluorescens ?
-
 ?
1.14.13.84 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 ?
-
 ?
1.14.13.84 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 ?
-
 ?
1.14.13.84 propiophenone + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl propionate + NADP+ + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.84 HAPMO
-
 Pseudomonas fluorescens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.13.84 30
-
 assay at Pseudomonas fluorescens

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.14.13.84 0.5
-
 4-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 0.6
-
 4-fluoroacetophenone pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 1.2
-
 butyrophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 1.7
-
 4-methoxyacetophenone pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 2.1
-
 2,4-Pentanedione pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 2.2
-
 benzaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 2.5
-
 isobutyrophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 3.9
-
 acetylcyclohexane pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 4.1
-
 Hydroxyacetone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 4.7
-
 methylphenyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 4.8
-
 3-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 5
-
 cyclohexane carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 6.3
-
 4-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 6.7
-
 2-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 6.7
-
 bicyclohept-2-en-6-one pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 7.3
-
 methyl 4-tolyl sulfide pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 7.4
-
 3-chloro-2-butanone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 7.6
-
 4-hydroxybenzaldehyde pH 8, 30°C Pseudomonas fluorescens
1.14.13.84 7.8
-
 2-acetylpyridine pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 8.6
-
 2-pyrrole carboxaldehyde pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 9.4
-
 2-acetylpyrrole pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 11
-
 propiophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 11.9
-
 4-hydroxypropiophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 12.6
-
 4-hydroxyacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 12.7
-
 4-aminoacetophenone pH 7.5, 30°C Pseudomonas fluorescens
1.14.13.84 13.2
-
 acetophenone pH 7.5, 30°C Pseudomonas fluorescens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.13.84 7.5
-
 assay at Pseudomonas fluorescens

Cofactor

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