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Literature summary for 1.1.3.38 extracted from

  • van den Heuvel, R.H.H.; Laane, C.; van Berkel, W.J.H.
    Exploring the biocatalytic potential of vanillyl-alcohol oxidase by site-directed mutagenesis (2001), Adv. Synth. Catal., 343, 515-520.
No PubMed abstract available
Search for more literature for 1.1.3.38

Application

Application Comment Organism
synthesis synthesis of natural vanillin from capsaicin using a two-enzyme system of carboxylesterase from liver and vanillyl-alcohol oxidase Penicillium simplicissimum

Protein Variants

Protein Variants Comment Organism
D170A only 50% of the FAD is covalently bound. With vanilly alcohol, eugenol, and 4-(methoxymethyl)phenol the mutant enzyme is more than 1000fold less active than the wild-type enzyme Penicillium simplicissimum
D170A/T457E produces (S)-1-(4'-hydroxyphenyl)ethanol from 4-ethylphenol. The wild-type enzyme produces (R)-1-(4'-hydroxyphenyl)ethanol Penicillium simplicissimum
D170E with vanilly alcohol, eugenol, and 4-(methoxymethyl)phenol the mutant enzyme is 5-fold to 100fold less active than the wild-type enzyme Penicillium simplicissimum
D170N no FAD is covalently bound. With vanilly alcohol, eugenol, and 4-(methoxymethyl)phenol the mutant enzyme is more than 1000fold less active than the wild-type enzyme Penicillium simplicissimum
D170S with vanilly alcohol, eugenol, and 4-(methoxymethyl)phenol the mutant enzyme is more than 1000fold less active than the wild-type enzyme Penicillium simplicissimum
D170S/T457E produces (S)-1-(4'-hydroxyphenyl)ethanol from 4-ethylphenol. The wild-type enzyme produces (R)-1-(4'-hydroxyphenyl)ethanol Penicillium simplicissimum

Organism

Organism UniProt Comment Textmining
Penicillium simplicissimum
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-
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-methoxy-4-hydroxybenzyl alcohol + O2 i.e. vanillyl alcohol Penicillium simplicissimum 3-methoxy-4-hydroxybenzaldehyde + H2O2 i.e. vanillin ?
4-butylphenol + O2
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 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
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 Penicillium simplicissimum (R)-1-(4'-hydroxyphenyl)ethanol + H2O2 product formed by wild-type enzyme and mutant enzymes D170S and D170A.D170A/T457E and D170S/T457E form (S)-1-(4'-hydroxyphenyl)ethanol. 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
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 Penicillium simplicissimum 4-isopropenylphenol + ? mutant D170E: 8% alcohol + 92% alkene. Mutant D170S: 80% alcohol + 20% alkene ?
4-n-propylphenol + O2
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 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-sec-butylphenol + O2
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 Penicillium simplicissimum ? mutant D170E: 1% alcohol + 99% alkene. Mutant D170S: 78% alcohol + 22% alkene ?
eugenol + O2 + H2O
-
 Penicillium simplicissimum coniferyl alcohol + H2O2
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 ?
additional information short-chain 4-alkylphenols are predominantly hydroxylated to (R)-1-(4'-hydroxyphenyl) alcohols, whereas medium-chain 4-alkylphenols are dehydrogenated to the corresponding 1-(4'-hydroxyphenyl) alkenes Penicillium simplicissimum ?
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 ?

Synonyms

Synonyms Comment Organism
VAO
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 Penicillium simplicissimum

Cofactor

Cofactor Comment Organism Structure
FAD covalently bound in wild-type enzyme and mutant enzymes D170E and D170S, 50% of the FAD is covalently bound in mutant enzyme D170A and no FAD is covalently bound in mutant enzyme D170N Penicillium simplicissimum