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Literature summary for 1.14.18.1 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
Search for more literature for 1.14.18.1

Inhibitors

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

KM Value [mM]

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

Metals/Ions

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Agaricus bisporus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
commercial preparation
-
 Agaricus bisporus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2 L-dopa + O2
-
 Agaricus bisporus 2 dopaquinone + 2 H2O
-
 ?
2-methylresorcinol + O2 acts as enzyme substrate and inhibitor, low activity Agaricus bisporus ?
-
 ?
4-ethoxyphenol + O2
-
 Agaricus bisporus ?
-
 ?
4-ethylresorcinol + O2 acts as enzyme substrate and inhibitor Agaricus bisporus ?
-
 ?
4-methoxyphenol + O2
-
 Agaricus bisporus ?
-
 ?
4-methylresorcinol + O2 acts as enzyme substrate and inhibitor Agaricus bisporus ?
-
 ?
hydroquinone + O2
-
 Agaricus bisporus ?
-
 ?
L-tyrosine + O2
-
 Agaricus bisporus dopaquinone + H2O
-
 ?
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 ?
-
 ?
phenol + O2
-
 Agaricus bisporus ?
-
 ?
resorcinol + O2 acts as enzyme substrate and inhibitor Agaricus bisporus ?
-
 ?

Synonyms

Synonyms Comment Organism
mushroom tyrosinase
-
 Agaricus bisporus

Temperature Optimum [°C]

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

Turnover Number [1/s]

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

pH Optimum

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

IC50 Value

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

kcat/KM [mM/s]

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