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Literature summary extracted from

  • Garcia-Jimenez, A.; Teruel-Puche, J.A.; Berna, J.; Rodriguez-Lopez, J.N.; Tudela, J.; Garcia-Ruiz, P.A.; Garcia-Canovas, F.
    Characterization of the action of tyrosinase on resorcinols (2016), Bioorg. Med. Chem., 24, 4434-4443 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.18.1 2-Methylresorcinol acts as enzyme substrate and inhibitor Agaricus bisporus
1.14.18.1 4-ethylresorcinol acts as enzyme substrate and inhibitor Agaricus bisporus
1.14.18.1 4-methylresorcinol acts as enzyme substrate and inhibitor Agaricus bisporus
1.14.18.1 additional information structural mechanism of resorcinol inhibitors, overview Agaricus bisporus
1.14.18.1 resorcinol acts as enzyme substrate and inhibitor Agaricus bisporus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.18.1 additional information
-
 additional information Michaelis-Menten kinetics Agaricus bisporus
1.14.18.1 0.08
-
 4-methoxyphenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.117
-
 4-ethylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.17
-
 4-ethoxyphenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.203
-
 4-methylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.21
-
 L-tyrosine pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.46
-
 resorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.7
-
 phenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 0.92
-
 hydroquinone pH 7.0, 25°C Agaricus bisporus
1.14.18.1 2.7
-
 2-Methylresorcinol pH 7.0, 25°C Agaricus bisporus

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.18.1 Cu2+ a copper-containing enzyme Agaricus bisporus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.18.1 2 L-dopa + O2 Agaricus bisporus
-
 2 dopaquinone + 2 H2O
-
 ?
1.14.18.1 L-tyrosine + O2 Agaricus bisporus
-
 dopaquinone + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.18.1 Agaricus bisporus
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.18.1 commercial preparation
-
 Agaricus bisporus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.18.1 2 L-dopa + O2
-
 Agaricus bisporus 2 dopaquinone + 2 H2O
-
 ?
1.14.18.1 2-methylresorcinol + O2 acts as enzyme substrate and inhibitor, low activity Agaricus bisporus ?
-
 ?
1.14.18.1 4-ethoxyphenol + O2
-
 Agaricus bisporus ?
-
 ?
1.14.18.1 4-ethylresorcinol + O2 acts as enzyme substrate and inhibitor Agaricus bisporus ?
-
 ?
1.14.18.1 4-methoxyphenol + O2
-
 Agaricus bisporus ?
-
 ?
1.14.18.1 4-methylresorcinol + O2 acts as enzyme substrate and inhibitor Agaricus bisporus ?
-
 ?
1.14.18.1 hydroquinone + O2
-
 Agaricus bisporus ?
-
 ?
1.14.18.1 L-tyrosine + O2
-
 Agaricus bisporus dopaquinone + H2O
-
 ?
1.14.18.1 additional information resorcinol and some derivatives, 4-ethylresorcinol, 2-methylresorcinol and 4-methylresorcinol, all act as substrates of tyrosinase if the catalytic cycle is completed with a reductant such as ascorbic acid or an o-diphenol such as 4-tert-butylcatechol. The reaction can also be carried out, adding hydrogen peroxide to the reaction medium. Measurement of the activity of the enzyme after pre-incubation with resorcinol, 4-ethylresorcinol or 4-methylresorcinol points to an apparent loss of activity at short times. If the measurements are extended over longer times, a burst is observed and the enzymatic activity is recovered, demonstrating that these compounds are not suicide substrates of the enzyme. These effects are not observed with 2-methylresorcinol. The docking results indicate that the binding of met-tyrosinase with these resorcinols occurs in the same way, but not with 2-methylresorcinol, due to steric hindrance. The enzyme assays are performed in preenceof ascorbic acid or hydrogen peroxide. Molecular docking simulations and modeling, overview Agaricus bisporus ?
-
 ?
1.14.18.1 phenol + O2
-
 Agaricus bisporus ?
-
 ?
1.14.18.1 resorcinol + O2 acts as enzyme substrate and inhibitor Agaricus bisporus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.18.1 mushroom tyrosinase
-
 Agaricus bisporus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.18.1 25
-
 assay at Agaricus bisporus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.14.18.1 6
-
 4-ethylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 7.73
-
 4-methylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 7.9
-
 L-tyrosine pH 7.0, 25°C Agaricus bisporus
1.14.18.1 9.94
-
 2-Methylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 12.7
-
 phenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 18.34
-
 resorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 101.5
-
 hydroquinone pH 7.0, 25°C Agaricus bisporus
1.14.18.1 132
-
 4-ethoxyphenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 184.2
-
 4-methoxyphenol pH 7.0, 25°C Agaricus bisporus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.18.1 7
-
 assay at Agaricus bisporus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.18.1 0.0011
-
 pH 7.0, 25°C, inhibition of the diphenolase activity of mushroom tyrosinase Agaricus bisporus 4-methylresorcinol
1.14.18.1 0.0019
-
 pH 7.0, 25°C, inhibition of the monophenolase activity of mushroom tyrosinase Agaricus bisporus 4-ethylresorcinol
1.14.18.1 0.0033
-
 pH 7.0, 25°C, inhibition of the diphenolase activity of mushroom tyrosinase Agaricus bisporus 4-ethylresorcinol
1.14.18.1 0.00931
-
 pH 7.0, 25°C, inhibition of the monophenolase activity of mushroom tyrosinase Agaricus bisporus 4-ethylresorcinol
1.14.18.1 0.652
-
 pH 7.0, 25°C, inhibition of the diphenolase activity of mushroom tyrosinase Agaricus bisporus resorcinol
1.14.18.1 0.717
-
 pH 7.0, 25°C, inhibition of the diphenolase activity of mushroom tyrosinase Agaricus bisporus 2-Methylresorcinol
1.14.18.1 1.125
-
 pH 7.0, 25°C, inhibition of the monophenolase activity of mushroom tyrosinase Agaricus bisporus resorcinol
1.14.18.1 1.415
-
 pH 7.0, 25°C, inhibition of the monophenolase activity of mushroom tyrosinase Agaricus bisporus 2-Methylresorcinol

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.14.18.1 3.7
-
 2-Methylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 18.1
-
 phenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 37.6
-
 L-tyrosine pH 7.0, 25°C Agaricus bisporus
1.14.18.1 38.1
-
 4-methylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 39.9
-
 resorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 51.3
-
 4-ethylresorcinol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 110.3
-
 hydroquinone pH 7.0, 25°C Agaricus bisporus
1.14.18.1 776.5
-
 4-ethoxyphenol pH 7.0, 25°C Agaricus bisporus
1.14.18.1 2300
-
 4-methoxyphenol pH 7.0, 25°C Agaricus bisporus