Page last updated: 2024-10-24

D-amino-acid oxidase activity

Definition

Target type: molecularfunction

Catalysis of the reaction: a D-amino acid + H2O + O2 = a 2-oxo acid + NH3 + hydrogen peroxide. [EC:1.4.3.3]

D-amino-acid oxidase activity is a catalytic function that specifically oxidizes D-amino acids, which are stereoisomers of the naturally occurring L-amino acids. This enzymatic activity involves the removal of two hydrogen atoms from the α-carbon of a D-amino acid, resulting in the formation of an α-keto acid and ammonia. The reaction requires molecular oxygen as the oxidant, which is reduced to hydrogen peroxide as a byproduct.

D-amino-acid oxidases belong to the flavin-containing oxidoreductase family, and their active site contains a flavin adenine dinucleotide (FAD) cofactor. The catalytic cycle of D-amino-acid oxidase begins with the binding of a D-amino acid substrate to the enzyme, followed by the reduction of the FAD cofactor to FADH2. This reduction step involves the transfer of two electrons from the substrate to FAD, which is accompanied by the release of ammonia. The reduced FAD cofactor then reacts with molecular oxygen, regenerating the oxidized FAD and generating hydrogen peroxide. The α-keto acid product is released from the enzyme, and the cycle is ready to begin anew.

D-amino-acid oxidase activity plays a crucial role in various biological processes, including:

* **Amino acid metabolism:** D-amino-acid oxidases catalyze the breakdown of D-amino acids, which are not typically found in proteins but can be produced by various metabolic pathways or through bacterial contamination.
* **Neurotransmission:** Some D-amino acids, such as D-serine, act as neuromodulators, and their levels are regulated by D-amino-acid oxidase activity.
* **Immune response:** D-amino-acid oxidase activity is involved in the production of reactive oxygen species, which contribute to immune responses.

The specific D-amino acids that can be oxidized by D-amino-acid oxidases vary depending on the enzyme. Some D-amino-acid oxidases exhibit broad substrate specificity, while others are more selective. For example, the enzyme D-amino acid oxidase (DAO) found in mammals primarily oxidizes D-serine and D-alanine.'
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Proteins (1)

ProteinDefinitionTaxonomy
D-amino-acid oxidaseA D-amino-acid oxidase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P14920]Homo sapiens (human)

Compounds (33)

CompoundDefinitionClassesRoles
benzoic acidaromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.

benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.

Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.
benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
malonic aciddicarboxylic acid : Any carboxylic acid containing two carboxy groups.

malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.
alpha,omega-dicarboxylic acidhuman metabolite
niacinNiacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.

nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.

vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).
pyridine alkaloid;
pyridinemonocarboxylic acid;
vitamin B3
antidote;
antilipemic drug;
EC 3.5.1.19 (nicotinamidase) inhibitor;
Escherichia coli metabolite;
human urinary metabolite;
metabolite;
mouse metabolite;
plant metabolite;
vasodilator agent
kojic acid4-pyranones;
enol;
primary alcohol
Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent
3-hydroxy-2-oxoindole3-hydroxyindolin-2-one : An oxindole that is 1,3-dihydro-2H-indol-2-one substituted by a hydroxy group at position 3.

3-hydroxyindolin-2-one: structure in first source
hydroxyindoles;
oxindoles
thiophene-3-carboxylic acidthiophene-3-carboxylic acid: structure in first source
3-aminobenzoic acid3-aminobenzoic acid : An aminobenzoic acid carrying an amino group at position 3.

3-aminobenzoic acid: RN given refers to parent cpd
aminobenzoic acid
adrenaloneadrenalone: RN given refers to parent cpdaromatic ketone
5-chlorosalicylic acid5-chlorosalicylic acid : A monohydroxybenzoic acid that is 2-hydroxybenzoic acid (salicylic acid) in which the hydrogen at position 5 is replaced by chlorine.

5-chlorosalicylic acid: major metabolite of meseclazone; RN given refers to parent cpd
chlorobenzoic acid;
monochlorobenzenes;
monohydroxybenzoic acid
5-methylpyrazole-3-carboxylic acid5-methyl-pyrazole-3-carboxylic acid : A memebr of the class of pyrazoles that is 1H-pyrazole with methyl and carboxylic acid group substituents at positions 5 and 3 respectively.

5-methylpyrazole-3-carboxylic acid: structure
monocarboxylic acid;
pyrazoles
metabolite
3-aminopyridine
thiophene-2-carboxylatethiophene-2-carboxylic acid : A thiophenecarboxylic acid in which the carboxy group is located at position 2.thiophenecarboxylic acid
2-hydroxy benzimidazole2-hydroxy benzimidazole: structure in first source
2-pyrrolecarboxylic acid2-pyrrolecarboxylic acid: hypocalcemic action; structure

pyrrole-2-carboxylic acid : A pyrrolecarboxylic acid that is 1H-pyrrole carrying a carboxy substituent at position 2.
pyrrolecarboxylic acidplant metabolite
3-hydroxypicolinic acidmonocarboxylic acid;
monohydroxypyridine
MALDI matrix material
3-hydroxy-1-benzopyran-2-one3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source

hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent.
hydroxycoumarin
oxiniacic acidaromatic carboxylic acid;
pyridines
6-aminonicotinic acid6-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 6 of the pyridine ring.

6-aminonicotinic acid: RN given refers to parent cpd
aminonicotinic acid;
aminopyridine;
aromatic amine
metabolite
2,3-dihydroxypyridine2,3-dihydroxypyridine: affects thyroid function

pyridine-2,3-diol : A dihydroxypyridine in which the two hydroxy groups are located at positions 2 and 3.
dihydroxypyridine
5-hydroxynicotinic acidaromatic carboxylic acid;
pyridines
5-fluorosalicylic acid5-fluorosalicylic acid: structure given in first source; product from action of alkaline phosphatase on 5-fluorosalicyl phosphate; forms highly fluorescent terbium ternary complex
indole-2-carboxylic acidindolyl carboxylic acid
2-aminonicotinic acid2-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 2 of the pyridine ring.

2-aminonicotinic acid: structure in first source

aminonicotinic acid : An aromatic amino acid that is nicotinic acid in which one of the hydrogens attached to the pyridine ring is replaced by an amino group. A 'closed class'.
aminonicotinic acid;
aminopyridine
metabolite
3-aminopicolinic acid
5-aminonicotinic acid5-aminonicotinic acid : An aminonicotinic acid in which the amino group is situated at position 5 of the pyridine ring.

5-aminonicotinic acid: an inhibitor of D-aspartate oxidase; structure in first source
aminonicotinic acid;
aminopyridine;
aromatic amine
metabolite
crotonic acidbutenoic acid : Any C4, straight-chain fatty acid containing one double bond.

crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.

crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL
2-butenoic acidplant metabolite
3-coumaric acid3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.

3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline

trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.
3-coumaric acid
pseudoginsenoside f11
3-hydroxyquinolin-2(1h)-one3-hydroxyquinolin-2(1H)-one: structure in first source

dihydroxyquinoline : Any hydroxyquinoline in which the number of hydroxy substituents is specified as two.
hydroxyquinoline;
quinolone
6-Chlorobenzo[d]isoxazol-3-olbenzisoxazole
ceftriaxone1,2,4-triazines;
1,3-thiazoles;
cephalosporin;
oxime O-ether
antibacterial drug;
drug allergen;
EC 3.5.2.6 (beta-lactamase) inhibitor
mofegiline
sun