(2,5-dioxoimidazolidin-4-yl)urea

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Uric acid is oxidized enzymatically by uricase to allantoin and hydrogen peroxide at about pH 7. The stoichiometry of the enzyme reaction proper, regardless of buffer or pH, is given by equation (1), i.e., the transfer of an electron pair from the urate monoanion to oxygen, yielding an unstable acid intermediate (1-carboxy-2,4,6,8-tetraazabicycl [3,3,0]-octa-4-en-3,7-dione), and hydrogen peroxide. The stoichiometry of the enzyme reaction proper

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Allantoin (1.58 g) was stirred with meta-iodobenzyl bromide (2.97 g) in DMF (25 ml) at 21° under nitrogen and sodium hydride (60% oil dispersion; 0.40 g) was added over 5 min. After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3. The separated aqueous layer was extracted with more EtOAc and the combined organic layers were washed with water and brine twice. After drying (MgSO4), the solution was concentrated to 20 ml. After 1 h the solid was collected by filtration and washed with EtOAc. The residue was boiled with EtOAc (50 ml) and the slurry was allowed to cool. The solid was collected by filtration, washed with ethyl acetate and dried to give the title compound (0.507 g). LCMS RT=2.44 min After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3 The separated aqueous layer was extracted with more EtOAc the combined organic layers were washed with water and brine twice After drying (MgSO4) the solution was concentrated to 20 ml After 1 h the solid was collected by filtration washed with EtOAc to cool The solid was collected by filtration washed with ethyl acetate dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Allantoin (1.58 g) was stirred with meta-iodobenzyl bromide (2.97 g) in DMF (25 ml) at 21° under nitrogen and sodium hydride (60% oil dispersion; 0.40 g) was added over 5 min. After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3. The separated aqueous layer was extracted with more EtOAc and the combined organic layers were washed with water and brine twice. After drying (MgSO4), the solution was concentrated to 20 ml. After 1 h the solid was collected by filtration and washed with EtOAc. The residue was boiled with EtOAc (50 ml) and the slurry was allowed to cool. The solid was collected by filtration, washed with ethyl acetate and dried to give the title compound (0.507 g). LCMS RT=2.44 min After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3 The separated aqueous layer was extracted with more EtOAc the combined organic layers were washed with water and brine twice After drying (MgSO4) the solution was concentrated to 20 ml After 1 h the solid was collected by filtration washed with EtOAc to cool The solid was collected by filtration washed with ethyl acetate dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For these enzymes, glucose oxidase catalyzes the reaction of β-D-glucose, water, and oxygen to produce hydrogen peroxide and gluconic acid. Galactose oxidase catalyzes the reaction of D-galactose and oxygen to produce hydrogen peroxide and D-galacto-hexodialdose. Urate oxidase catalyzes the reaction of uric acid, water, and oxygen to produce hydrogen peroxide, allantoin, and carbon dioxide. Choline oxidase catalyzes the reaction of choline and oxygen to produce hydrogen peroxide and betaine aldehyde. D-amino acid oxidase catalyzes the reaction of D-amino acids such as D-proline, D-methionine, D-isoleucine, D-alanine, D-valine, or D-phenylalanine with water and oxygen to produce hydrogen peroxide, ammonia, and the α-keto acid corresponding to the D-amino acid being oxidized. D-glutamate oxidase catalyzes the reaction of D-glutamic acid, water, and oxygen to produce hydrogen peroxide, ammonia, and 2-ketoglutarate. Glycine oxidase catalyzes the reaction of glycine, water, and oxygen to produce hydrogen peroxide, ammonia, and glyoxylic acid. Glycolic acid oxidase (also known as 2-hydroxyacid oxidase) catalyzes the reaction of glycolic acid and oxygen to produce 2-ketoacetic acid and hydrogen peroxide. L-sorbose oxidase catalyzes the reaction of L-sorbose and oxygen to produce 5-dehydro-D-fructose and hydrogen peroxide. Alcohol oxidase catalyzes the reaction of a lower primary alcohol or an unsaturated alcohol and oxygen to produce the corresponding aldehyde and hydrogen peroxide. Amine oxidase catalyzes the reaction of an amine, typically a primary amine, but also, in some cases, a secondary or tertiary amine, water, and oxygen to produce the corresponding aldehyde, ammonia, and hydrogen peroxide. In an illustrative reaction, glucose oxidase catalyzes the reaction of β-D-glucose, water, and oxygen during application to the outer ear to produce hydrogen peroxide and gluconic acid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Urate oxidase catalyzes the interaction of urate, water and oxygen to produce hydrogen peroxide, allantoin and carbon dioxide;

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 30.6 g of glyoxylic acid butyl ester butyl hemiacetal (0.15 mol), 30.0 g of urea (0.5 mol), 300 g of n-butanol and 7.5 g of 8% strength butanolic sulfuric acid was heated at 85° C. for a total of 4 hours. After the reaction had ended, the suspension formed was cooled to room temperature, whereupon a colorless precipitate separated out, which was filtered off, washed with methanol and dried in vacuo at 75° C. 23.1 g, that is to say 66% of theory, of crystalline allantoin acid butyl ester were obtained by this reaction. the suspension formed was cooled to room temperature, whereupon a colorless precipitate separated out which was filtered off washed with methanol dried in vacuo at 75° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 26.4 g of glyoxylic acid propyl ester propyl hemiacetal (0.15 mol), 30.0 g of urea (0.5 mol), 600 g of propanol and 7.5 g of 8% strength propanolic sulfuric acid was heated under reflux for 4 hours. Thereafter, the reaction had ended and the reaction mixture was cooled to room temperature, whereupon a colorless precipitate separated out, which was filtered off, washed with methanol and dried in vacuo at 50° C. 13.6 g, that is to say 42% of theory, of crystalline allantoin acid propyl ester were obtained by this reaction. was heated under reflux for 4 hours separated out which was filtered off washed with methanol dried in vacuo at 50° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 22.2 g of glyoxylic acid ethyl ester ethyl hemiacetal (0.15 mol), 30.0 g of urea (0.5 mol), 90 g of ethanol and 7.5 g of 8% strength ethanolic sulfuric acid was heated under reflux for 4 hours. Thereafter, the reaction had ended and the reaction mixture was cooled to room temperature, whereupon a colorless precipitate separated out, which was filtered off, washed three times with ethanol and dried in vacuo at 70° C. 24.5 g, that is to say 80% of theory, of allantoin acid ethyl ester were obtained by this reaction. was heated under reflux for 4 hours separated out which was filtered off washed three times with ethanol dried in vacuo at 70° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Urate oxidase catalyzes the interaction of urate, water and oxygen to produce hydrogen peroxide, allantoin and carbon dioxide;

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Uric acid is oxidized enzymatically by uricase to allantoin and hydrogen peroxide at about pH 7. The stoichiometry of the enzyme reaction proper, regardless of buffer or pH, is given by equation (1), i.e., the transfer of an electron pair from the urate monoanion to oxygen, yielding an unstable acid intermediate (1-carboxy-2,4,6,8-tetraazabicycl [3,3,0]-octa-4-en-3,7-dione), and hydrogen peroxide. The stoichiometry of the enzyme reaction proper

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Allantoin (1.58 g) was stirred with meta-iodobenzyl bromide (2.97 g) in DMF (25 ml) at 21° under nitrogen and sodium hydride (60% oil dispersion; 0.40 g) was added over 5 min. After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3. The separated aqueous layer was extracted with more EtOAc and the combined organic layers were washed with water and brine twice. After drying (MgSO4), the solution was concentrated to 20 ml. After 1 h the solid was collected by filtration and washed with EtOAc. The residue was boiled with EtOAc (50 ml) and the slurry was allowed to cool. The solid was collected by filtration, washed with ethyl acetate and dried to give the title compound (0.507 g). LCMS RT=2.44 min After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3 The separated aqueous layer was extracted with more EtOAc the combined organic layers were washed with water and brine twice After drying (MgSO4) the solution was concentrated to 20 ml After 1 h the solid was collected by filtration washed with EtOAc to cool The solid was collected by filtration washed with ethyl acetate dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For these enzymes, glucose oxidase catalyzes the reaction of β-D-glucose, water, and oxygen to produce hydrogen peroxide and gluconic acid. Galactose oxidase catalyzes the reaction of D-galactose and oxygen to produce hydrogen peroxide and D-galacto-hexodialdose. Urate oxidase catalyzes the reaction of uric acid, water, and oxygen to produce hydrogen peroxide, allantoin, and carbon dioxide. Choline oxidase catalyzes the reaction of choline and oxygen to produce hydrogen peroxide and betaine aldehyde. D-amino acid oxidase catalyzes the reaction of D-amino acids such as D-proline, D-methionine, D-isoleucine, D-alanine, D-valine, or D-phenylalanine with water and oxygen to produce hydrogen peroxide, ammonia, and the α-keto acid corresponding to the D-amino acid being oxidized. D-glutamate oxidase catalyzes the reaction of D-glutamic acid, water, and oxygen to produce hydrogen peroxide, ammonia, and 2-ketoglutarate. Glycine oxidase catalyzes the reaction of glycine, water, and oxygen to produce hydrogen peroxide, ammonia, and glyoxylic acid. Glycolic acid oxidase (also known as 2-hydroxyacid oxidase) catalyzes the reaction of glycolic acid and oxygen to produce 2-ketoacetic acid and hydrogen peroxide. L-sorbose oxidase catalyzes the reaction of L-sorbose and oxygen to produce 5-dehydro-D-fructose and hydrogen peroxide. Alcohol oxidase catalyzes the reaction of a lower primary alcohol or an unsaturated alcohol and oxygen to produce the corresponding aldehyde and hydrogen peroxide. Amine oxidase catalyzes the reaction of an amine, typically a primary amine, but also, in some cases, a secondary or tertiary amine, water, and oxygen to produce the corresponding aldehyde, ammonia, and hydrogen peroxide. In an illustrative reaction, glucose oxidase catalyzes the reaction of β-D-glucose, water, and oxygen during application to the outer ear to produce hydrogen peroxide and gluconic acid.