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xanthine + H2O + O2 = urate + H2O2
xanthine + H2O + O2 = urate + H2O2
mechanism
-
xanthine + H2O + O2 = urate + H2O2
hydrogen-bonding arrangement of the substrate-bound complex at the active site, and proposed mechanism of the purine oxidation reaction by XOR
-
xanthine + H2O + O2 = urate + H2O2
catalytic mechanism of xanthine oxidoreductase, overview
-
xanthine + H2O + O2 = urate + H2O2
favored mechanism for the reaction with xanthine, overview
-
xanthine + H2O + O2 = urate + H2O2
reaction mechanism for xanthine oxidase, overview. Catalysis is initiated by base-assisted nucleophilic attack of the equatorial Mo-OH on the C-8 carbon of xanthine with concomitant hydride transfer from C-8 to Mo=S, which simultaneously results in reduction of Mo(VI) to Mo(IV). Reoxidation of the molybdenum center occurs by electron transfer to the other redox-active centers of the enzyme, accompanied by deprotonation of the Mo-SH bond and displacement of bound product by hydroxide from solvent to regenerate the Mo-OH group
xanthine + H2O + O2 = urate + H2O2
reaction mechanism of XOR and binding modes of the substrate xanthine, overview. The oxidative hydroxylation of purine substrates takes place at the molybdenum center. Reducing equivalents introduced there are then transferred via two [2Fe-2S] centers to the FAD cofactor where reduction of the physiological electron acceptors occurs, NAD+ in the case of the dehydrogenase form, XDH, or O2 in the oxidase form, XO, of the enzyme occur
-
xanthine + H2O + O2 = urate + H2O2
reaction mechanism of XOR and binding modes of the substrate xanthine, overview. The oxidative hydroxylation of purine substrates takes place at the molybdenum center. Reducing equivalents introduced there are then transferred via two [2Fe-2S] centers to the FAD cofactor where reduction of the physiological electron acceptors occurs, NAD+ in the case of the dehydrogenase form, XDH, or O2 in the oxidase form, XO, of the enzyme occur
xanthine + H2O + O2 = urate + H2O2
reaction mechanism, detailed overview. The reaction is initiated by proton abstraction from the Mo-OH group by Glu1261, the active-site base, followed by nucleophilic attack on the carbon to be hydroxylated, and hydride transfer to the Mo-S double bond. Suitable substrate orientation, overview. Arg880 is involved in stablizing the transition state in the course of nucleophilic attack, overview
-
xanthine + H2O + O2 = urate + H2O2
mechanism of the reductive half-reaction of xanthine oxidase
xanthine + H2O + O2 = urate + H2O2
the catalytic reaction of xanthine oxidase is initiated by abstraction of a proton from the Mo-OH group by a conserved active site glutamate residue. The oxidative hydroxylation of xanthine to uric acid takes place at the molybdenum center and results in the two-electron reduction of the metal from Mo(VI) to Mo(IV). The enzyme is subsequently re-oxidized by NAD+ or molecular oxygen in a reaction that occurs at the FAD cofactor
-
xanthine + H2O + O2 = urate + H2O2
the catalytic reaction of xanthine oxidase is initiated by abstraction of a proton from the Mo-OH group by a conserved active site glutamate residue. The oxidative hydroxylation of xanthine to uric acid takes place at the molybdenum center and results in the two-electron reduction of the metal from Mo(VI) to Mo(IV). The enzyme is subsequently re-oxidized by NAD+ or molecular oxygen in a reaction that occurs at the FAD cofactor
-
-
xanthine + H2O + O2 = urate + H2O2
-
-
-
-
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(carboxymethyl)cellulose with endohydrolysed (1->4)-beta-D-glucosidic linkages + H2O + O2
?
-
-
-
-
r
1,3-dimethylxanthine + H2O + O2
1,3-dimethylurate + H2O2
-
-
-
-
?
1,7-dimethylxanthine + H2O + O2
1,7-dimethylurate + H2o2
-
-
-
-
?
1-methyl-2-hydroxypurine + H2O + O2
1-methyl-2-hydroxy-7,9-dihydropurin-8-one + H2O2
-
-
-
?
1-methylxanthine + H2O + O2
1-methylurate + H2O2
2,3-dihydroxybenzaldehyde + H2O + O2
2,3-dihydroxybenzoate + H2O2
-
-
-
?
2,5-dihydroxybenzaldehyde + H2O + O2
?
-
-
-
-
?
2,6-diaminopurine + H2O + O2
2,6-diamino-7,9-dihydro-8H-purin-8-one
-
-
-
-
?
2-amino-4-hydroxypteridine + H2O + O2
?
2-amino-4-hydroxypterin + H2O + O2
? + H2O2
-
substrate inhibition kinetic pattern
-
-
?
2-amino-6-chloro-purine + H2O + O2
2-amino-6-chloro-7,9-dihydro-purin-8-one + H2O2
-
-
-
-
?
2-hydroxybenzaldehyde + H2O + O2
2-hydroxybenzoate + H2O2
-
-
-
-
?
2-mercaptopurine + H2O + O2
8-hydroxy-2-mercaptopurine + H2O2
-
no conversion to 2-thioxanthine
-
-
?
2-methoxybenzaldehyde + H2O + O2
2-methoxybenzoate + H2O2
-
-
-
-
?
2-methylbenzaldehyde + H2O + O2
2-methylbenzoate + H2O2
-
-
-
-
?
2-nitrobenzaldehyde + H2O + O2
2-nitrobenzoate + H2O2
-
-
-
-
?
2-oxo-6-methylpurine + H2O + O2
? + H2O2
-
low activity
-
-
?
2-thioxanthine + H2O + O2
2-thiourate + H2O2
-
-
-
-
?
2-thioxanthine + H2O + O2
2-thiouric acid + H2O2
-
-
-
-
?
3,4-dihydroxybenzaldehyde + H2O + O2
3,4-dihydroxybenzoate + H2O2
-
-
-
-
?
3,4-dimethoxybenzaldehyde + H2O + O2
3,4-dimethoxybenzoate + H2O2
-
-
-
-
?
3-hydroxy-4-methoxybenzaldehyde + H2O + O2
3-hydroxy-4-methoxybenzoate + H2O2
-
-
-
-
?
3-hydroxybenzaldehyde + H2O + O2
3-hydroxybenzoate + H2O2
-
-
-
-
?
3-methoxybenzaldehyde + H2O + O2
3-methoxybenzoate + H2O2
-
-
-
-
?
3-methylbenzaldehyde + H2O + O2
3-methylbenzoate + H2O2
-
-
-
-
?
3-methylhypoxanthine + H2O + O2
3-methylxanthine + H2O2
-
-
-
?
3-methylxanthine + H2O + O2
3-methylurate + H2O2
-
-
-
-
?
3-nitrobenzaldehyde + H2O + O2
3-nitrobenzoate + H2O2
-
-
-
-
?
4-hydroxy-3-methoxybenzaldehyde + H2O + O2
4-hydroxy-3-methoxybenzoate + H2O2
-
-
-
-
?
4-hydroxybenzaldehyde + H2O + O2
4-hydroxybenzoate + H2O2
-
-
-
-
?
4-hydroxyphenylglycoaldehyde + H2O + O2
?
-
-
-
-
?
4-methoxybenzaldehyde + H2O + O2
4-methoxybenzoate + H2O2
-
-
-
-
?
4-methylbenzaldehyde + H2O + O2
4-methylbenzoate + H2O2
-
-
-
-
?
4-nitrobenzaldehyde + H2O + O2
4-nitrobenzoate + H2O2
-
-
-
-
?
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-3H-pyrimidin-4-one + H2O + O2
?
-
-
-
-
?
6'-deoxyacyclovir + H2O + O2
acyclovir + H2O2
-
prodrug of the antiviral agent acyclovir
-
?
6,8-dihydroxypurine + H2O + O2
?
-
-
-
-
?
6,8-dihydroxypurine + H2O + O2
? + H2O2
6,8-dihydroxypurine binding structure, overview
-
-
?
6-amino-5-bromo-1H-pyrimidin-2-one + H2O + O2
?
-
-
-
-
?
6-amino-5-bromo-3H-pyrimidin-4-one + H2O + O2
?
-
-
-
-
?
6-amino-5-bromopyrimidine + H2O + O2
?
-
-
-
-
?
6-cyanopurine + H2O + O2
6-cyano-7,9-dihydropurine-8-one
-
-
-
?
6-formylpterin + H2O + O2
?
-
-
-
-
?
6-formylpterin + H2O + O2
? + H2O2
-
-
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
6-mercaptopurine + H2O + O2
6-mercapto-7,9-dihydropurin-8-one + H2O2
-
4.4% of activity with xanthin
-
?
6-mercaptopurine + H2O + O2
?
-
an anticancer drug
-
-
?
6-thioxanthine + H2O + O2
6-thiourate + H2O2
6-thioxanthine + H2O + O2
6-thiouric acid + H2O2
-
-
-
-
?
7-alkylpteridin-4-one + H2O + O2
7-alkyllumazine + H2O2
-
-
-
?
7-methylxanthine + H2O + O2
7-methylurate + H2O2
-
-
-
-
?
7-phenylpteridin-4-one + H2O + O2
7-phenyllumazine + H2O2
-
-
-
?
7H-pyrrolo[2,3-d]pyrimidin-2(1H)-one + H2O + O2
?
-
-
-
-
?
7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one + H2O + O2
?
-
-
-
-
?
7H-pyrrolo[2,3-d]pyrimidine + H2O + O2
?
-
-
-
-
?
acetaldehyde + H2O + O2
acetic acid + H2O2
adenine + H2O + O2
6-amino-7,9-dihydropurin-8-one + H2O2
adenine + H2O + O2
? + H2O2
-
substrate inhibition kinetic pattern
-
-
?
aldehyde + indophenol
?
-
-
-
-
r
allopurinol + H2O + O2
oxypurinol + H2O2
benzaldehyde + H2O + O2
benzoate + H2O2
butanal + H2O + O2
butanoate + H2O2
-
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
dibromoacetonitrile + H2O + O2
?
-
-
-
-
r
formaldehyde + H2O + O2
?
-
-
-
-
r
formycin B + H2O + O2
?
-
-
-
-
?
FYX-051 + O2 + H2O
?
-
the structure of bovine XOR exposed to the slow-reacting substrate FYX-051 shows a covalent intermediate of the hydroxylation reaction, in which the hydroxyl oxygen bridged the molybdenumatom and the acceptor carbon atom of the aromatic ring of the substrate
-
-
?
glyceraldehyde-3-phosphate + H2O + O2
?
-
-
-
-
?
glyceryl trinitrate + 2,3-dihydroxybenzaldehyde
?
-
-
-
-
?
glyceryl trinitrate + NADH
? + NAD+ + H2O
-
-
further reaction of organic nitrite with thiols or ascorbate leads to generation of NO or nitrosothiols
-
?
glyceryl trinitrate + xanthine
urate + ?
-
-
-
-
?
guanine + H2O + O2
2-amino-7,9-dihydro-1H-purine-6,8-dione + H2O2
hypoxanthine + 2 H2O + 2 O2
urate + 2 H2O2
hypoxanthine + H2O + O2
urate + H2O2
-
-
-
-
?
hypoxanthine + NAD+ + H2O
xanthine + NADH + H+
indole-3-acetaldehyde + H2O + O2
?
-
-
-
-
?
indole-3-aldehyde + H2O + O2
?
-
-
-
-
?
isosorbide dinitrate + 2,3-dihydroxybenzaldehyde
?
-
-
-
-
?
isosorbide dinitrate + NADH
? + NAD+ + H2O
-
-
further reaction of organic nitrite with thiols or ascorbate leads to generation of NO or nitrosothiols
-
?
isosorbide dinitrate + xanthine
urate + ?
-
-
-
-
?
lumazine + H2O + O2
? + H2O2
-
classical Michaelis-Menten hyperbolic saturation kinetic pattern
-
-
?
N-methylnicotinamide + H2O + O2
?
-
poor oxidation reaction
-
-
r
N1-methylnicotinamide + H2O + O2
?
NADH + H2O + O2
NAD+ + H2O2
NADPH + indophenol
?
-
-
-
-
r
nitrate + 2,3-dihydroxybenzaldehyde
nitrite + ?
-
-
-
-
?
nitrate + NADH
nitrite + NAD+ + H2O
nitrate + xanthine
nitrite + urate + ?
-
-
-
-
?
nitrite + 2,3-dihydroxybenzaldehyde
NO + ?
-
NO generation occurs under aerobic conditions and is regulated by O2 tension, pH, nitrite, and reducing substrate concentrations
-
-
?
nitrite + NADH
NO + NAD+ + H2O
nitrite + O2 + hypoxanthine
peroxynitrite + ?
-
-
-
-
?
nitrite + O2 + pterin
peroxynitrite + ?
-
-
-
-
?
nitrite + xanthine
NO + ?
o-hydroxybenzaldehyde + H2O + O2
o-hydroxybenzoate + H2O2
-
-
-
?
organic nitrate + NADH
organic nitrite + NAD+ + H2O
-
organic nitrite is the initial product in the process of xanthine oxidase mediated organic nitrate biotransformation and is the precursor of NO and nitrosothiols, serving as the link between organic nitrate and soluble guanylyl cyclase
-
-
?
propanal + H2O + O2
propanoate + H2O2
-
-
-
?
pterin + H2O + O2
?
-
fluorometric assay method
-
-
?
pterin + H2O + O2
isoxanthopterin + H2O2
-
-
-
?
pterine + NAD+
? + H2O + NADH
-
-
-
?
purine + H2O + O2
7,9-dihydropurin-8-one + H2O2
purine + NAD+
? + H2O + NADH
-
-
-
?
pyridine 3-aldehyde + H2O + O2
?
-
-
-
-
r
pyridine-2-aldehyde + H2O + O2
?
-
-
-
-
?
pyridine-3-aldehyde + H2O + O2
?
-
-
-
-
?
pyridine-4-aldehyde + H2O + O2
?
-
-
-
-
?
pyrimidine derivatives + H2O + O2
?
salicylaldehyde + H2O + O2
salicylic acid + H2O2
-
-
-
?
succinate semialdehyde + H2O + O2
succinate + H2O2
-
-
-
-
?
xanthine + 2,6-dichlorophenolindophenol + H2O
urate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
xanthine + cytochrome c + H2O
urate + reduced cytochrome c
-
-
-
-
?
xanthine + H2O + O2
?
-
-
-
-
?
xanthine + H2O + O2
superoxide + urate + ?
-
-
-
-
?
xanthine + H2O + O2
urate + H2O2
xanthine + H2O + O2
uric acid + H2O2
xanthine + methylene blue + O2
urate + reduced methylene blue
-
-
-
-
?
xanthine + NAD+ + H2O
urate + NADH
-
-
-
?
xanthine + NO2-
uric acid + NO
xanthine + O2 + H2O
urate + H2O2
xanthine + thionine + O2
urate + reduced thionine
-
-
-
-
?
xanthopterin + H2O + O2
?
-
-
-
-
?
xanthopterin + H2O + O2
? + H2O2
-
substrate activation kinetic pattern
-
-
?
additional information
?
-
1-methylxanthine + H2O + O2
1-methylurate + H2O2
-
-
-
?
1-methylxanthine + H2O + O2
1-methylurate + H2O2
-
-
-
?
1-methylxanthine + H2O + O2
1-methylurate + H2O2
-
-
-
-
?
1-methylxanthine + H2O + O2
1-methylurate + H2O2
-
-
-
-
?
2-amino-4-hydroxypteridine + H2O + O2
?
-
-
-
-
r
2-amino-4-hydroxypteridine + H2O + O2
?
-
-
-
-
r
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
-
-
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
-
production of superoxide radicals
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
-
a two-step reaction with 6-thioxanthine as intermediate
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
-
-
-
-
?
6-mercaptopurine + 2 H2O + 2 O2
6-thiouric acid + 2 H2O2
-
an anticancer prodrug, no activation by xanthine oxidase but conversion to the inactive metabolite 6-thiouric acid, catabolism, overview
-
-
?
6-thioxanthine + H2O + O2
6-thiourate + H2O2
-
-
-
?
6-thioxanthine + H2O + O2
6-thiourate + H2O2
-
-
-
-
?
acetaldehyde + H2O + O2
acetic acid + H2O2
-
-
-
?
acetaldehyde + H2O + O2
acetic acid + H2O2
-
-
-
?
adenine + H2O + O2
6-amino-7,9-dihydropurin-8-one + H2O2
-
-
-
?
adenine + H2O + O2
6-amino-7,9-dihydropurin-8-one + H2O2
-
no activity with adenine
-
-
?
adenine + H2O + O2
6-amino-7,9-dihydropurin-8-one + H2O2
-
-
-
?
allopurinol + H2O + O2
?
-
-
-
-
?
allopurinol + H2O + O2
?
-
-
-
-
?
allopurinol + H2O + O2
oxypurinol + H2O2
-
-
allopurinol is a conventional substrate that generates superoxide radicals during its oxidation
-
?
allopurinol + H2O + O2
oxypurinol + H2O2
-
allopurinol is a substrate and a competitive inhibitor for xanthine oxidase, it binds irreversibly at the active site reducing molybdenum VI to IV
-
-
?
allopurinol + H2O + O2
oxypurinol + H2O2
-
allopurinol is a substrate and a competitive inhibitor for xanthine oxidase, it binds irreversibly at the active site reducing molybdenum VI to IV
-
-
?
benzaldehyde + H2O + O2
benzoate + H2O2
-
-
-
-
?
benzaldehyde + H2O + O2
benzoate + H2O2
-
-
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
carboxylic aldehyde + H2O + O2
carboxylic acid + H2O2
-
enzyme is implicated in the control of various redox reactions in the cell, in milk: assures absorption of iron from the gut, coupling antibacterial effect via the lactoperoxidase system
-
-
?
guanine + H2O + O2
2-amino-7,9-dihydro-1H-purine-6,8-dione + H2O2
-
-
-
-
?
guanine + H2O + O2
2-amino-7,9-dihydro-1H-purine-6,8-dione + H2O2
-
53.3% of activity with xanthin
-
?
hypoxanthine + 2 H2O + 2 O2
urate + 2 H2O2
-
-
-
1.17.3.2 xanthine oxidase
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