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Literature summary for 1.14.13.84 extracted from

  • Kamerbeek, N.M.; Moonen, M.J.; van der Ven, J.G.; van Berkel, W.J.H.; Fraaije, M.W.; Janssen, D.B.
    4- Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB: a novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds (2001), Eur. J. Biochem., 268, 2547-2557.
    View publication on PubMed

Application

Application Comment Organism
additional information as acylcatechols are valuable synthons for the fine chemical industry, HAPMO might develop as a useful biocatalytic tool Pseudomonas fluorescens

Cloned(Commentary)

Cloned (Comment) Organism
hapE, expression in Escherichia coli BL21(DE3)pLysS, sequence analysis Pseudomonas fluorescens

Protein Variants

Protein Variants Comment Organism
G490A strictly conserved glycine, dramatic effect of mutation on binding and oxidation of NADPH Pseudomonas fluorescens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.003
-
4-aminoacetophenone pH 8, 30°C Pseudomonas fluorescens
0.012
-
4-hydroxypropiophenone pH 8, 30°C Pseudomonas fluorescens
0.039
-
4-hydroxyacetophenone pH 8, 30°C Pseudomonas fluorescens
0.064
-
NADPH pH 8, 30°C Pseudomonas fluorescens
0.101
-
4-hydroxybenzaldehyde pH 8, 30°C Pseudomonas fluorescens
0.161
-
4-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
0.38
-
4-hydroxy-3-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
0.541
-
4-methoxyacetophenone pH 8, 30°C Pseudomonas fluorescens
1.04
-
4-fluoroacetophenone pH 8, 30°C Pseudomonas fluorescens
2.27
-
acetophenone pH 8, 30°C Pseudomonas fluorescens

Localization

Localization Comment Organism GeneOntology No. Textmining
soluble recombinant HAPMO Pseudomonas fluorescens
-
-

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
70000
-
2 * 70000, SDS-PAGE, 2 * 71884, sequence calculation Pseudomonas fluorescens
71884
-
2 * 70000, SDS-PAGE, 2 * 71884, sequence calculation Pseudomonas fluorescens
140000
-
gel filtration 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 catalyzes the first step in the degradation of 4-hydroxyacetophenone 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 Pseudomonas fluorescens ACB catalyzes the first step in the degradation of 4-hydroxyacetophenone 4-hydroxyphenyl acetate + NADP+ + H2O
-
?

Organism

Organism UniProt Comment Textmining
Pseudomonas fluorescens
-
ACB
-
Pseudomonas fluorescens Q93TJ5
-
-
Pseudomonas fluorescens ACB
-
ACB
-
Pseudomonas fluorescens ACB Q93TJ5
-
-

Purification (Commentary)

Purification (Comment) Organism
wild-type, 25fold, and recombinant HAPMO Pseudomonas fluorescens

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
5.5
-
pH 8, 30°C Pseudomonas fluorescens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
-
Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
-
Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-aminoacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 1-(4-aminophenyl)ethanol + NADP+ + H2O
-
?
4-aminoacetophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens 1-(4-aminophenyl)ethanol + NADP+ + H2O
-
?
4-aminoacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB 1-(4-aminophenyl)ethanol + NADP+ + H2O
-
?
4-fluoroacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-fluorophenyl acetate + NADP+ + H2O
-
?
4-fluoroacetophenone + NADPH + H+ + O2 strictly NADPH-dependent, poor substrate Pseudomonas fluorescens 4-fluorophenyl acetate + NADP+ + H2O
-
?
4-hydroxy-3-methylacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-hydroxy-3-methylphenyl acetate + NADP+ + H2O
-
r
4-hydroxy-3-methylacetophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens 4-hydroxy-3-methylphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 strictly NADPH-dependent, tight coupling between NADPH oxidation and substrate oxygenation Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O product is instable ?
4-hydroxyacetophenone + NADPH + H+ + O2 catalyzes the first step in the degradation of 4-hydroxyacetophenone Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxyacetophenone + NADPH + H+ + O2 strictly NADPH-dependent, tight coupling between NADPH oxidation and substrate oxygenation Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O product is instable ?
4-hydroxyacetophenone + NADPH + H+ + O2 catalyzes the first step in the degradation of 4-hydroxyacetophenone Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens ?
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-hydroxybenzoate + NADP+ + H2O
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-hydroxyphenyl propionate + NADP+ + H2O
-
?
4-hydroxypropiophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens 4-hydroxyphenyl propionate + NADP+ + H2O
-
?
4-hydroxypropiophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB 4-hydroxyphenyl propionate + NADP+ + H2O
-
?
4-hydroxypropiophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens ACB 4-hydroxyphenyl propionate + NADP+ + H2O
-
?
4-methoxyacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methoxyphenyl acetate + NADP+ + H2O
-
?
4-methoxyacetophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens 4-methoxyphenyl acetate + NADP+ + H2O
-
?
4-methylacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methylphenyl acetate + NADP+ + H2O
-
?
4-methylacetophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens 4-methylphenyl acetate + NADP+ + H2O
-
?
4-methylacetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB 4-methylphenyl acetate + NADP+ + H2O
-
?
acetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl acetate + NADP+ + H2O
-
?
acetophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens phenyl acetate + NADP+ + H2O
-
?
acetophenone + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB phenyl acetate + NADP+ + H2O
-
?
acetophenone + NADPH + H+ + O2 strictly NADPH-dependent Pseudomonas fluorescens ACB phenyl acetate + NADP+ + H2O
-
?
additional information catalyzes the Baeyer-Villiger oxidation of aromatic compounds, converts a wide range of acetophenones via a Baeyer-Villiger rearrangement reaction into the corresponding phenyl acetates, the highest catalytic efficiency is observed with compounds bearing an electron donating substituent at the para position of the aromatic ring, in the absence of substrate the enzyme can act as an NADPH oxidase forming hydrogen peroxide, not: cyclohexanone, cyclopentanone, NADH Pseudomonas fluorescens ?
-
?
additional information catalyzes the Baeyer-Villiger oxidation of aromatic compounds, converts a wide range of acetophenones via a Baeyer-Villiger rearrangement reaction into the corresponding phenyl acetates, the highest catalytic efficiency is observed with compounds bearing an electron donating substituent at the para position of the aromatic ring, in the absence of substrate the enzyme can act as an NADPH oxidase forming hydrogen peroxide, not: cyclohexanone, cyclopentanone, NADH Pseudomonas fluorescens ACB ?
-
?

Subunits

Subunits Comment Organism
homodimer 2 * 70000, SDS-PAGE, 2 * 71884, sequence calculation Pseudomonas fluorescens

Synonyms

Synonyms Comment Organism
HAPMO
-
Pseudomonas fluorescens

Temperature Optimum [°C]

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

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.6
-
4-fluoroacetophenone pH 8, 30°C Pseudomonas fluorescens
1.7
-
4-methoxyacetophenone pH 8, 30°C Pseudomonas fluorescens
4.5
-
acetophenone pH 8, 30°C Pseudomonas fluorescens
5.4
-
4-hydroxy-3-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
6.3
-
4-methylacetophenone pH 8, 30°C Pseudomonas fluorescens
7.6
-
4-hydroxybenzaldehyde pH 8, 30°C Pseudomonas fluorescens
9.3
-
NADPH pH 8, 30°C Pseudomonas fluorescens
10.1
-
4-hydroxyacetophenone pH 8, 30°C Pseudomonas fluorescens
10.6
-
4-hydroxypropiophenone pH 8, 30°C Pseudomonas fluorescens
12.3
-
4-aminoacetophenone pH 8, 30°C Pseudomonas fluorescens

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
FAD FAD-dependent, each subunit contains a noncovalently bound FAD molecule, both molecules participate in the reduction reaction, molecular oxygen is able to reoxidize the flavin cofactor Pseudomonas fluorescens
additional information not: NADH Pseudomonas fluorescens
NADPH strictly NADPH-dependent Pseudomonas fluorescens