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Literature summary for 1.1.3.38 extracted from

  • Van der Heuvel, R.H.H.; Fraaije, M.W.; Laane, C.; van Berkel, W.J.H.
    Regio- and stereospecific conversion of 4-alkylphenols by the covalent flavoprotein vanillyl-alcohol oxidase (1998), J. Bacteriol., 180, 5646-5651.
    View publication on PubMedView publication on EuropePMC

Inhibitors

Inhibitors Comment Organism Structure
4-vinylphenol
-
Penicillium simplicissimum
Medium-chain 4-alkylphenol product inhibition Penicillium simplicissimum

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.002
-
4-n-butylphenol
-
Penicillium simplicissimum
0.004
-
4-Propylphenol
-
Penicillium simplicissimum
0.006
-
2-Methoxy-4-n-propylphenol
-
Penicillium simplicissimum
0.008
-
4-n-pentylphenol
-
Penicillium simplicissimum
0.009
-
4-Ethylphenol
-
Penicillium simplicissimum
0.016
-
4-isopropylphenol
-
Penicillium simplicissimum
0.026
-
(S)-1-(4'-hydroxyphenyl)ethanol
-
Penicillium simplicissimum
0.03
-
(R,S)-1-(4'-Hydroxyphenyl)propanol
-
Penicillium simplicissimum
0.042
-
4-n-heptylphenol
-
Penicillium simplicissimum
0.065
-
4-(3'-methylcrotyl)phenol
-
Penicillium simplicissimum
0.072
-
4-sec-butylphenol
-
Penicillium simplicissimum
0.077
-
5-indanol
-
Penicillium simplicissimum
0.094
-
5,6,7,8-tetrahydro-2-naphthol
-
Penicillium simplicissimum
0.1
-
2-(4'-hydroxyphenyl)ethanol
-
Penicillium simplicissimum
0.128
-
1-(4'-Hydroxyphenyl)-2-butanone
-
Penicillium simplicissimum
0.222
-
(R)-1-(4'-hydroxyphenol)ethanol
-
Penicillium simplicissimum

Organism

Organism UniProt Comment Textmining
Penicillium simplicissimum
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-1-(4'-Hydroxyphenyl)ethanol + O2
-
Penicillium simplicissimum ?
-
?
(R,S)-1-(4'-Hydroxyphenyl)propanol + O2
-
Penicillium simplicissimum ?
-
?
(S)-1-(4'-Hydroxyphenyl)ethanol + O2
-
Penicillium simplicissimum ?
-
?
1-(4'-Hydroxyphenyl)-2-butanone + O2
-
Penicillium simplicissimum ?
-
?
1-(4'-Hydroxyphenyl)-2-butanone + O2 i.e., frambinon Penicillium simplicissimum ?
-
r
2-(4'-Hydroxyphenyl)ethanol + O2
-
Penicillium simplicissimum ?
-
?
2-Methoxy-4-n-propylphenol + O2
-
Penicillium simplicissimum 1-(4'-Hydroxy-3'-methoxyphenyl)propanol 90% 4-hydroxyphenylalcohol + 10% 4-hydroxyphenylalkene. Less than 1% cis-4-hydroxyphenylalkene + more than 99% trans-4-hydroxyphenylalkene ?
3-(4'-Hydroxyphenyl)propanol + O2
-
Penicillium simplicissimum ?
-
?
4-(3'-methylcrotyl)phenol + O2
-
Penicillium simplicissimum 4-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]phenol + 4-[(1E)-3-methylbuta-1,3-dien-1-yl]phenol 40% 4-hydroxyphenylalcohol + 60% 4-hydroxyphenylalkene. 100% trans-4-hydroxyphenylalkene ?
4-ethylphenol + O2
-
Penicillium simplicissimum 1-(4'-hydroxyphenyl)ethanol + 4-vinylphenol + 4-hydroxyacetophenone 76% 4-hydroxyphenolalcohol + 24% 4-hydroxyphenylalkene ?
4-isopropylphenol + O2
-
Penicillium simplicissimum 4-(2-hydroxypropan-2-yl)phenol + 4-isopropenylphenol 20% 4-hydroxyphenylalcohol + 80% 4-hydroxyphenylalkene ?
4-n-butylphenol + O2
-
Penicillium simplicissimum 4-[(1E)-but-1-en-1-yl]phenol + 4-[(1Z)-but-1-en-1-yl]phenol 93% cis-4-hydroxyphenylalkene + 7% trans-4-hydroxyphenylalkene ?
4-n-heptylphenol + O2
-
Penicillium simplicissimum 4-[(1E)-hept-1-en-1-yl]phenol + 4-[(1Z)-hept-1-en-1-yl]phenol 50% cis-4-hydroxyphenylalkene + 50% trans-4-hydroxyphenylalkene ?
4-n-pentylphenol + O2
-
Penicillium simplicissimum 4-[(1E)-pent-1-en-1-yl]phenol + 4-[(1Z)-pent-1-en-1-yl]phenol + H2O2 60% cis-4-hydroxyphenylalkene + 40% trans-4-hydroxyphenylalkene ?
4-Propylphenol + O2 4-n-propylphenol Penicillium simplicissimum 1-(4'-Hydroxyphenyl)propanol + 4-propenylphenol + 1-(4'-hydroxyphenyl)propanone 45% cis-4-hydroxyphenylalkene + 55% trans-4-hydroxyphenylalkene ?
4-sec-butylphenol + O2
-
Penicillium simplicissimum 4-(2-hydroxybutan-2-yl)phenol + 4-(but-1-en-2-yl)phenol + 4-[(2Z)-but-2-en-2-yl]phenol 26% 4-hydroxyphenylalcohol + 74% 4-hydroxyphenylalkene. 100% cis-4-hydroxyphenylalkene ?
5,6,7,8-tetrahydro-2-naphthol + O2
-
Penicillium simplicissimum ? 4% 4-hydroxyphenylalcohol + 94% 4-hydroxyphenylalkene + 2% 4-hydroxyphenylalkanone ?
5-indanol + O2
-
Penicillium simplicissimum ? 16% 4-hydroxyphenylalcohol + 24% 4-hydroxyphenylalkene + 60% 4-hydroxyphenylalkanone ?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.004
-
2-(4'-hydroxyphenyl)ethanol
-
Penicillium simplicissimum
0.1
-
3-(4'-hydroxyphenol)propanol
-
Penicillium simplicissimum
0.3
-
4-n-pentylphenol
-
Penicillium simplicissimum
0.3
-
1-(4'-Hydroxyphenyl)-2-butanone
-
Penicillium simplicissimum
0.5
-
4-sec-butylphenol
-
Penicillium simplicissimum
0.5
-
5-indanol
-
Penicillium simplicissimum
0.7
-
5,6,7,8-tetrahydro-2-naphthol
-
Penicillium simplicissimum
1.2
-
4-n-butylphenol
-
Penicillium simplicissimum
1.3
-
4-isopropylphenol
-
Penicillium simplicissimum
1.4
-
4-(3'-methylcrotyl)phenol
-
Penicillium simplicissimum
2.5
-
4-Ethylphenol
-
Penicillium simplicissimum
3
-
(R,S)-1-(4'-Hydroxyphenyl)propanol
-
Penicillium simplicissimum
3.2
-
2-Methoxy-4-n-propylphenol
-
Penicillium simplicissimum
4.2
-
4-n-Propylphenol
-
Penicillium simplicissimum
4.4
-
(S)-1-(4'-hydroxyphenyl)ethanol
-
Penicillium simplicissimum
13
-
eugenol
-
Penicillium simplicissimum