Application | Comment | Organism |
---|---|---|
additional information | potential of HAPMO for biotechnological applications | Pseudomonas fluorescens |
Cloned (Comment) | Organism |
---|---|
hapE gene, expression in Escherichia coli TOP10 | Pseudomonas fluorescens |
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 | 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 | UniProt | Comment | Textmining |
---|---|---|---|
Pseudomonas fluorescens | - |
- |
- |
Pseudomonas fluorescens ACB | - |
- |
- |
Purification (Comment) | Organism |
---|---|
recombinant HAPMO | Pseudomonas fluorescens |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O | enantioselectivity | Pseudomonas fluorescens |
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 | Comment | Organism |
---|---|---|
HAPMO | - |
Pseudomonas fluorescens |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
30 | - |
assay at | Pseudomonas fluorescens |
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 Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.5 | - |
assay at | Pseudomonas fluorescens |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
flavin | flavin-containing enzyme | Pseudomonas fluorescens | |
NADPH | NADPH-dependent | Pseudomonas fluorescens |