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-Canovas, F.
Action of tyrosinase on alpha and beta-arbutin A kinetic study (2017), PLoS ONE, 12, e0177330 .

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Activating Compound

Activating Compound	Comment	Organism	Structure
H2O2	the addition of hydrogen peroxide transforms Em to Eox, which is able to hydroxylate alpha/beta-arbutin, although the o-quinone that is originated is unstable	Agaricus bisporus

Inhibitors

Inhibitors	Comment	Organism	Structure
4-hexylresorcinol	-	Agaricus bisporus
4-n-butylresorcinol	-	Agaricus bisporus
alpha-arbutin	inhibition of monophenolase activity, the inhibitory activity of beta-arbutin is higher compared to alpha-arbutin, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions	Agaricus bisporus
ascorbic acid	-	Agaricus bisporus
beta-arbutin	inhibition of monophenolase activity, the inhibitory activity of beta-arbutin is higher compared to alpha-arbutin, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions	Agaricus bisporus
ellagic acid	-	Agaricus bisporus
hydroquinone	-	Agaricus bisporus
additional information	the compounds with resorcinol structure can also act as substrates, react with tyrosinase producing reactive quinones	Agaricus bisporus
oxyresveratrol	-	Agaricus bisporus

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
additional information	-	additional information	Michaelis-Menten steady-state kinetics	Agaricus bisporus
3	-	beta-arbutin	pH 7.0, 25°C	Agaricus bisporus
6.5	-	alpha-arbutin	pH 7.0, 25°C	Agaricus bisporus

Metals/Ions

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

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.
4-hexylresorcinol + O2	-	Agaricus bisporus	?	-	?
4-n-butylresorcinol + O2	-	Agaricus bisporus	?	-	?
alpha-arbutin + O2	alpha-arbutin also has a weaker inhibitory effect on the monophenolase activity of the enzyme, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions	Agaricus bisporus	?	-	?
beta-arbutin + O2	alpha-arbutin also has a weaker inhibitory effect on the monophenolase activity of the enzyme, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions	Agaricus bisporus	?	-	?
ellagic acid + O2	-	Agaricus bisporus	?	-	?
hydroquinone + O2	-	Agaricus bisporus	?	-	?
additional information	the oxy form of tyrosinase (oxytyrosinase) hydroxylates alpha and beta-arbutin in ortho position of the phenolic hydroxyl group, giving rise to a complex formed by met-tyrosinase with the hydroxylated alpha or beta-arbutin. This complex can evolve in two ways: by oxidizing the originated o-diphenol to o-quinone and deoxy-tyrosinase, or by delivering the o-diphenol and met-tyrosinase to the medium, which would produce the self-activation of the system. If 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate is used, the o-quinone is attacked, so that it becomes an adduct, which can be oxidized by another molecule of o-quinone, generating o-diphenol in the medium. In this way, the system reaches the steady state and originates a chromophore, which, in turn, has a high absorptivity in the visible spectrum and can be measured. The catalysis cannot be quantified because the quinones generated in both cases are unstable. 3-Methyl-2-benzothiazolinone hydrazone, MBTH, is a very potent nucleophile, which, in its deprotonated form, attacks the o-quinone generated by the action of tyrosinase on alpha- and beta-arbutin. The addition of hydrogen peroxide is required and transforms Em to Eox, which is able to hydroxylate arbutin, although the o-quinone that is originated is unstable	Agaricus bisporus	?	-	?
oxyresveratrol + O2	-	Agaricus bisporus	?	-	?
rhododendrol + O2	-	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
3.7	-	beta-arbutin	pH 7.0, 25°C	Agaricus bisporus
4.43	-	alpha-arbutin	pH 7.0, 25°C	Agaricus bisporus

pH Optimum

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

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Release 2023.1 (January 2023)