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 | 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 | UniProt | Comment | Textmining |
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Penicillium simplicissimum | - |
- |
- |
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 | - |
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 + 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 | - |
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-sec-butylphenol + O2 | - |
Penicillium simplicissimum | ? | mutant D170E: 1% alcohol + 99% alkene. Mutant D170S: 78% alcohol + 22% alkene | ? | |
eugenol + O2 + H2O | - |
Penicillium simplicissimum | coniferyl alcohol + H2O2 | - |
? | |
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 | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
VAO | - |
Penicillium simplicissimum |
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 |