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Literature summary for 1.1.3.38 extracted from

  • Ewing, T.A.; Nguyen, Q.T.; Allan, R.C.; Gygli, G.; Romero, E.; Binda, C.; Fraaije, M.W.; Mattevi, A.; van Berkel, W.J.H.
    Two tyrosine residues, Tyr-108 and Tyr-503, are responsible for the deprotonation of phenolic substrates in vanillyl-alcohol oxidase (2017), J. Biol. Chem., 292, 14668-14679 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.1.3.38

Cloned(Commentary)

Cloned (Comment) Organism
-
 Penicillium simplicissimum

Crystallization (Commentary)

Crystallization (Comment) Organism
tyrosine residues Tyr-108 and Tyr-503 are positioned to facilitate deprotonation of substrate's phenol groups Penicillium simplicissimum

Protein Variants

Protein Variants Comment Organism
Y108F deprotonation of the substrate's phenol group is impaired Penicillium simplicissimum
Y108F/Y503F deprotonation of the substrate's phenol group is impaired Penicillium simplicissimum
Y503F deprotonation of the substrate's phenol group is impaired Penicillium simplicissimum

Inhibitors

Inhibitors Comment Organism Structure
chavicol substrate inhibition Penicillium simplicissimum
isoeugenol competitive inhibitor, isoeugenol is predominantly in its deprotonated form when bound to wild-type VAOA, but predominantly in its protonated form when bound to the variants Y108F or Y503F Penicillium simplicissimum

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0065
-
 chavicol wild-type, pH 7.5, 25°C Penicillium simplicissimum
0.021
-
 chavicol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
0.067
-
 chavicol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum
0.074
-
 chavicol mutant Y108F/Y503F, pH 7.5, 25°C Penicillium simplicissimum
0.149
-
 Vanillyl alcohol wild-type, pH 7.5, 25°C Penicillium simplicissimum
0.99
-
 Vanillyl alcohol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
1.75
-
 Vanillyl alcohol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum

Organism

Organism UniProt Comment Textmining
Penicillium simplicissimum P56216
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
chavicol + O2 + H2O
-
 Penicillium simplicissimum coumaryl alcohol + H2O2
-
 ?
vanillyl alcohol + O2
-
 Penicillium simplicissimum vanillin + H2O2
-
 ?

Synonyms

Synonyms Comment Organism
VAOA
-
 Penicillium simplicissimum

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
52
-
 mutant Y108F/Y503F, midpoint of unfolding Penicillium simplicissimum
53
-
 mutants Y108F and Y503F, midpoint of unfolding Penicillium simplicissimum
55
-
 wild-type, midpoint of unfolding Penicillium simplicissimum

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.042
-
 Vanillyl alcohol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum
0.055
-
 Vanillyl alcohol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
0.13
-
 chavicol mutant Y108F/Y503F, pH 7.5, 25°C Penicillium simplicissimum
2.6
-
 Vanillyl alcohol wild-type, pH 7.5, 25°C Penicillium simplicissimum
3.3
-
 chavicol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
3.4
-
 chavicol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum
7.4
-
 chavicol wild-type, pH 7.5, 25°C Penicillium simplicissimum

Cofactor

Cofactor Comment Organism Structure
FAD covalently bound FAD Penicillium simplicissimum

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.45
-
 chavicol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
1.4
-
 chavicol mutant Y108F/Y503F, pH 7.5, 25°C Penicillium simplicissimum
2.9
-
 chavicol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum
7
-
 chavicol wild-type, pH 7.5, 25°C Penicillium simplicissimum

General Information

General Information Comment Organism
metabolism tyrosine residues Tyr-108 and Tyr-503 are positioned to facilitate deprotonation of substrate's phenol groups. The reduction of VAOA by chavicol or vanillyl alcohol occurs at two different rates: kobs1, which corresponds to its reaction with the deprotonated form of the substrate, and kobs2, which corresponds to its reaction with the protonated form of the substrate. In mutants Y108F, Y503F, and Y108F/Y503F, the relative contribution of kobs2 to the reduction is larger than in wild-type VAOA Penicillium simplicissimum

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.024
-
 Vanillyl alcohol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum
0.056
-
 Vanillyl alcohol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
1.8
-
 chavicol mutant Y108F/Y503F, pH 7.5, 25°C Penicillium simplicissimum
17
-
 Vanillyl alcohol wild-type, pH 7.5, 25°C Penicillium simplicissimum
51
-
 chavicol mutant Y108F, pH 7.5, 25°C Penicillium simplicissimum
157
-
 chavicol mutant Y503F, pH 7.5, 25°C Penicillium simplicissimum
1138
-
 chavicol wild-type, pH 7.5, 25°C Penicillium simplicissimum