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Literature summary for 1.1.3.38 extracted from

  • van den Heuvel, R.H.; Fraaije, M.W.; van Berkel, W.J.
    Direction of the reactivity of vanillyl-alcohol oxidase with 4-alkylphenols (2000), FEBS Lett., 481, 109-112.
    View publication on PubMed

Protein Variants

Protein Variants Comment Organism
D170E substrate preference is similar to wild-type enzyme, as the wild-type enzyme the mutant enzyme favors the production of alkenes Penicillium simplicissimum
D170S most active with branched-chain 4-alkylphenol, mutant enzyme favors the formation of alcohols Penicillium simplicissimum

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.006
-
4-butylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.01
-
4-n-Propylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.026
-
4-isopropylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.048
-
4-Ethylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.062
-
4-sec-butylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.075
-
4-sec-butylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.088
-
4-isopropylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum

Organism

Organism UniProt Comment Textmining
Penicillium simplicissimum
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-butylphenol + O2
-
Penicillium simplicissimum 4-but-1-en-1-ylphenol + 4-[(1R)-1-hydroxybutyl]phenol mutant D170E: 0% alcohol + 100% alkene. Mutant D170S: 82% alcohol + 18% alkene ?
4-ethylphenol + O2 + H2O
-
Penicillium simplicissimum (R)-1-(4'-hydroxyphenyl)ethanol + 4-vinylphenol + H2O2 product formed by wild-type enzyme and mutant enzyme D170S. The hydroxylation reaction in D170S is nearly completely blocked and this mutant converts short-chain alkylphenols to the corresponding alkenes. Mutant D170E: 8% alcohol + 92% alkene. Mutant D170S: 92% alcohol + 8% alkene ?
4-isopropylphenol + O2
-
Penicillium simplicissimum 4-isopropenylphenol + ? mutant D170E: 8% alcohol + 92% alkene. Mutant D170S: 80% alcohol + 20% alkene ?
4-n-propylphenol + O2
-
Penicillium simplicissimum 1-(4'-hydroxyphenyl)propanol + 4-(prop-1-en-1-yl)phenol mutant D170E: 7% alcohol + 93% alkene. Mutant D170S: 96% alcohol + 4% alkene ?
4-Propylphenol + O2
-
Penicillium simplicissimum 1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone
-
r
4-sec-butylphenol + O2
-
Penicillium simplicissimum ? mutant D170E: 1% alcohol + 99% alkene. Mutant D170S: 78% alcohol + 22% alkene ?
p-cresol + O2
-
Penicillium simplicissimum ?
-
?

Synonyms

Synonyms Comment Organism
VAO
-
Penicillium simplicissimum

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.0001
-
4-Ethylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.0001
-
4-butylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.0002
-
p-Cresol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.0002
-
4-n-Propylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.05
-
4-sec-butylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.09
-
4-sec-butylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.12
-
4-butylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.13
-
4-isopropylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.17
-
4-Ethylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum
0.18
-
4-isopropylphenol pH 7.5, 25°C, mutant enzyme D170S Penicillium simplicissimum
0.26
-
propylphenol pH 7.5, 25°C, mutant enzyme D170E Penicillium simplicissimum