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Information on EC 1.4.3.4 - monoamine oxidase and Organism(s) Aspergillus niger and UniProt Accession P46882
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1.4.3.4 monoamine oxidaseIUBMB Comments
A mitochondrial outer-membrane flavoprotein (FAD) that catalyses the oxidative deamination of neurotransmitters and biogenic amines . Acts on primary amines, and also on some secondary and tertiary amines. It differs from EC 1.4.3.21, primary-amine oxidase as it can oxidize secondary and tertiary amines but not methylamine. This enzyme is inhibited by acetylenic compounds such as chlorgyline, 1-deprenyl and pargyline but, unlike EC 1.4.3.21 and EC 1.4.3.22 (diamine oxidase), it is not inhibited by semicarbazide.
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Word Map
- 1.4.3.4
- dopamine
-
antidepressant
- parkinsonism
- platelet
-
dopaminergic
-
neurotransmitter
-
tricyclic
- norepinephrine
- pargyline
-
reuptake
- deprenyl
-
deamination
- clorgyline
- catecholamine
- noradrenaline
- 5-hydroxytryptamine
-
neuroprotective
-
serotonergic
- striatal
-
anxiety
-
psychiatric
- l-dopa
- fluoxetine
- catechol-o-methyltransferase
- 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
biogenic
- levodopa
-
mood
- reserpine
- imipramine
-
monoaminergic
- tryptamine
-
3,4-dihydroxyphenylacetic
- benzodiazepine
- mpp+
- amphetamine
-
nigrostriatal
-
homovanillic
-
5-hydroxyindoleacetic
-
noradrenergic
-
dopac
- 5-hydroxytryptophan
- 1-methyl-4-phenylpyridinium
- paroxetine
- desipramine
-
electroconvulsive
-
panic
-
mptp-induced
-
anticholinergic
-
antidepressant-like
- drug development
- analysis
- synthesis
- medicine
The taxonomic range for the selected organisms is: Aspergillus niger
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
monoamine oxidase, mao-b, mao-a, monoamine oxidase a, mao a, mao b, monoamine oxidase b, monoamine oxidase-b, monoamine oxidase-a, semicarbazide-sensitive amine oxidase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
adrenaline oxidase
-
-
-
-
epinephrine oxidase
-
-
-
-
MAO
monoamine oxidase
-
-
-
-
monoamine:O2 oxidoreductase (deaminating)
-
-
-
-
serotonin deaminase
-
-
-
-
tyraminase
-
-
-
-
tyramine oxidase
-
-
-
-
MAO
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Deamination
-
-
-
-
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
PATHWAY SOURCE
PATHWAYS
KEGG
-
-, -, -, -, -, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
amine:oxygen oxidoreductase (deaminating)
A mitochondrial outer-membrane flavoprotein (FAD) that catalyses the oxidative deamination of neurotransmitters and biogenic amines [3]. Acts on primary amines, and also on some secondary and tertiary amines. It differs from EC 1.4.3.21, primary-amine oxidase as it can oxidize secondary and tertiary amines but not methylamine. This enzyme is inhibited by acetylenic compounds such as chlorgyline, 1-deprenyl and pargyline but, unlike EC 1.4.3.21 and EC 1.4.3.22 (diamine oxidase), it is not inhibited by semicarbazide.
CAS REGISTRY NUMBER
COMMENTARY
9001-66-5
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1E)-1-phenylhexa-1,5-dien-3-amine + H2O + O2
-1-phenylhexa-1,5-dien-3-one + NH3 + H2O2
3% relative activity, enzyme variant D9
-
-
?
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline + H2O + O2
? + H2O2
-
-
-
?
1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
1-(2,4-difluorophenyl)ethan-1-amine + H2O + O2
1-(2,4-difluorophenyl)ethan-1-one + NH3 + H2O2
148% relative activity, enzyme variant D9
-
-
?
1-(2,6-difluorophenyl)ethan-1-amine + H2O + O2
1-(2,6-difluorophenyl)ethan-1-one + NH3 + H2O2
48% relative activity, enzyme variant D9
-
-
?
1-(2-bromo-4-fluorophenyl)ethan-1-amine + H2O + O2
1-(2-bromo-4-fluorophenyl)ethan-1-one + NH3 + H2O2
28% relative activity, enzyme variant D9
-
-
?
1-(2-chloro-4-fluorophenyl)ethan-1-amine + H2O + O2
1-(2-chloro-4-fluorophenyl)ethan-1-one + NH3 + H2O2
96% relative activity, enzyme variant D9
-
-
?
1-(2-chlorophenyl)ethan-1-amine + H2O + O2
1-(2-chlorophenyl)ethan-1-one + NH3 + H2O2
19% relative activity, enzyme variant D9
-
-
?
1-(2-fluorophenyl)ethan-1-amine + H2O + O2
1-(2-fluorophenyl)ethan-1-one + NH3 + H2O2
175% relative activity, enzyme variant D9
-
-
?
1-(2-fluorophenyl)propan-2-amine + H2O + O2
1-(2-fluorophenyl)propan-2-one + NH3 + H2O2
16% relative activity, enzyme variant D9
-
-
?
1-(2-methoxyphenyl)ethan-1-amine + H2O + O2
1-(2-methoxyphenyl)ethan-1-one + NH3 + H2O2
59% relative activity, enzyme variant D9
-
-
?
1-(2-methylphenyl)ethan-1-amine + H2O + O2
1-(2-methylphenyl)ethan-1-one + NH3 + H2O2
23% relative activity, enzyme variant D9
-
-
?
1-(3,5-difluorophenyl)ethan-1-amine + H2O + O2
1-(3,5-difluorophenyl)ethan-1-one + NH3 + H2O2
8% relative activity, enzyme variant D9
-
-
?
1-(3-fluorophenyl)ethan-1-amine + H2O + O2
1-(3-fluorophenyl)ethan-1-one + NH3 + H2O2
30% relative activity, enzyme variant D9
-
-
?
1-(3-methylphenyl)but-3-en-1-amine + H2O + O2
1-(3-methylphenyl)but-3-en-1-one + NH3 + H2O2
9% relative activity, enzyme variant D9
-
-
?
1-(4-bromo-3-fluorophenyl)but-3-en-1-amine + H2O + O2
1-(4-bromo-3-fluorophenyl)but-3-en-1-one + NH3 + H2O2
16% relative activity, enzyme variant D9
-
-
?
1-(4-bromophenyl)ethan-1-amine + H2O + O2
1-(4-bromophenyl)ethan-1-one + NH3 + H2O2
147% relative activity, enzyme variant D9
-
-
?
1-(4-chlorophenyl)but-3-en-1-amine + H2O + O2
1-(4-chlorophenyl)but-3-en-1-one + NH3 + H2O2
20% relative activity, enzyme variant D9
-
-
?
1-(4-chlorophenyl)ethan-1-amine + H2O + O2
1-(4-chlorophenyl)ethan-1-one + NH3 + H2O2
246% relative activity, enzyme variant D9
-
-
?
1-(4-fluoro-2-methylphenyl)ethan-1-amine + H2O + O2
1-(4-fluoro-2-methylphenyl)ethan-1-one + NH3 + H2O2
19% relative activity, enzyme variant D9
-
-
?
1-(4-fluoro-3-methylphenyl)ethan-1-amine + H2O + O2
1-(4-fluoro-3-methylphenyl)ethan-1-one + NH3 + H2O2
74% relative activity, enzyme variant D9
-
-
?
1-(4-fluorophenyl)ethan-1-amine + H2O + O2
1-(4-fluorophenyl)ethan-1-one + NH3 + H2O2
123% relative activity, enzyme variant D9
-
-
?
1-(4-iodophenyl)ethan-1-amine + H2O + O2
1-(4-iodophenyl)ethan-1-one + NH3 + H2O2
39% relative activity, enzyme variant D9
-
-
?
1-(4-methoxyphenyl)ethan-1-amine + H2O + O2
1-(4-methoxyphenyl)ethan-1-one + NH3 + H2O2
111% relative activity, enzyme variant D9
-
-
?
1-(4-methylphenyl)ethan-1-amine + H2O + O2
1-(4-methylphenyl)ethan-1-one + NH3 + H2O2
211% relative activity, enzyme variant D9
-
-
?
1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-amine + H2O + O2
1-(5,6,7,8-tetrahydrynaphthalen-2-yl)ethan-1-one + NH3 + H2O2
18% relative activity, enzyme variant D9
-
-
?
1-(6-methoxynaphthalen-2-yl)ethan-1-amine + H2O + O2
1-(6-methoxynaphthalen-2-yl)ethan-1-one + NH3 + H2O2
4% relative activity, enzyme variant D9
-
-
?
1-(adamantan-1-yl)ethan-1-amine + H2O + O2
1-(adamantan-1-yl)ethan-1-one + NH3 + H2O2
50% relative activity, enzyme variant D9
-
-
?
1-(furan-2-yl)ethan-1-amine + H2O + O2
1-(furan-2-yl)ethan-1-one + NH3 + H2O2
9% relative activity, enzyme variant D9
-
-
?
1-(naphthalen-2-yl)but-3-en-1-amine + H2O + O2
1-(naphthalen-2-yl)but-3-en-1-one + NH3 + H2O2
22% relative activity, enzyme variant D9
-
-
?
1-(pyridin-4-yl)but-3-en-1-amine + H2O + O2
1-(pyridin-4-yl)but-3-en-1-one + NH3 + H2O2
28% relative activity, enzyme variant D9
-
-
?
1-(pyrimidin-4-yl)ethan-1-amine + H2O + O2
1-(pyrimidin-4-yl)ethan-1-one + NH3 + H2O2
11% relative activity, enzyme variant D9
-
-
?
1-(thiophen-2-yl)ethan-1-amine + H2O + O2
1-(thiophen-2-yl)ethan-1-one + NH3 + H2O2
10% relative activity, enzyme variant D9
-
-
?
1-cyclohexylethan-1-amine + H2O + O2
1-cyclohexylethan-1-one + NH3 + H2O2
202% relative activity, enzyme variant D9
-
-
?
1-cyclopropyl-1-(4-fluorophenyl)methanamine + H2O + O2
cyclopropyl(4-fluorophenyl)methanone + NH3 + H2O2
184% relative activity, enzyme variant D9
-
-
?
1-phenylbut-3-en-1-amine + H2O + O2
1-phenylbut-3-en-1-one + NH3 + H2O2
5% relative activity, enzyme variant D9
-
-
?
1-phenylethan-1-amine + H2O + O2
1-phenylethan-1-one + NH3 + H2O2
100% relative activity, enzyme variant D9
-
-
?
1-phenylpropan-1-amine + H2O + O2
1-phenylpropan-1-one + NH3 + H2O2
34% relative activity, enzyme variant D9
-
-
?
1-phenylpropan-2-amine + H2O + O2
1-phenylpropan-2-one+ NH3 + H2O2
22% relative activity, enzyme variant D9
-
-
?
1-[4-(trifluoromethyl)phenyl]ethan-1-amine + H2O + O2
1-(4-trifluoromethylphenyl)ethan-1-one + NH3 + H2O2
125% relative activity, enzyme variant D9
-
-
?
2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-1-amine + H2O + O2
2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-1-one + NH3 + H2O2
12% relative activity, enzyme variant D9
-
-
?
2,3-dihydro-1H-inden-1-amine + H2O + O2
2,3-dihydro-1H-inden-1-one + NH3 + H2O2
199% relative activity, enzyme variant D9
-
-
?
2,3-dihydro-1H-inden-1-one + NH3 + H2O2
2,3-dihydro-1H-inden-1-amine + H2O + O2
165% relative activity, enzyme variant D11
-
-
?
2-methyl-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
2-methyl-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
4% relative activity, enzyme variant D9
-
-
?
3,4-dihydro-2H-1-benzopyran-4-amine + H2O + O2
2,3-dihydro-4H-1-benzopyran-4-one + NH3 + H2O2
22% relative activity, enzyme variant D9
-
-
?
4-bromo-2,3-dihydro-1H-inden-1-amine + H2O + O2
4-bromo-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
4% relative activity, enzyme variant D9
-
-
?
4-chloro-2,3-dihydro-1H-inden-1-amine + H2O + O2
4-chloro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
3% relative activity, enzyme variant D9
-
-
?
4-fluoro-2,3-dihydro-1H-inden-1-amine + H2O + O2
4-fluoro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
101% relative activity, enzyme variant D9
-
-
?
4-methyl-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
4-methyl-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
5% relative activity, enzyme variant D9
-
-
?
4-methylpentan-2-amine + H2O + O2
4-methylpentan-2-one + NH3 + H2O2
69% relative activity, enzyme variant D9
-
-
?
5,6-dihydro-4H-cyclopenta[b]thiophen-4-amine + H2O + O2
6-dihydro-4H-cyclopenta[b]thiophen-4-one + NH3 + H2O2
33% relative activity, enzyme variant D9
-
-
?
5-amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile + H2O + O2
5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile + NH3 + H2O2
103% relative activity, enzyme variant D9
-
-
?
5-fluoro-2,3-dihydro-1H-inden-1-amine + H2O + O2
5-fluoro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
242% relative activity, enzyme variant D9
-
-
?
5-methyl-2,3-dihydro-1H-inden-1-amine + H2O + O2
5-methyl-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
61% relative activity, enzyme variant D9
-
-
?
5-methyl-4,5,6,7-tetrahydro-1-benzofuran-4-amine + H2O + O2
5-methyl-4,5,6,7-tetrahydro-1-benzofuran-4-one + NH3 + H2O2
214% relative activity, enzyme variant D9
-
-
?
5-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulene + H2O + O2
6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one + methylamine + H2O2
6% relative activity, enzyme variant D9
-
-
?
6-chloro-2,3-dihydro-1H-inden-1-amine + H2O + O2
6-chloro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
103% relative activity, enzyme variant D9
-
-
?
6-fluoro-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
6-fluoro-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
155% relative activity, enzyme variant D9
-
-
?
6-fluoro-2,3-dihydro-1H-inden-1-amine + H2O + O2
6-fluoro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
143% relative activity, enzyme variant D9
-
-
?
6-methoxy-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
49% relative activity, enzyme variant D9
-
-
?
6-methylhept-1-en-4-amine + H2O + O2
6-methylhept-1-en-4-one + NH3 + H2O2
27% relative activity, enzyme variant D9
-
-
?
7-fluoro-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
7-fluoro-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
90% relative activity, enzyme variant D9
-
-
?
7-methyl-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
7-methyl-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
39% relative activity, enzyme variant D9
-
-
?
7-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-amine + H2O + O2
7-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one + NH3 + H2O2
14% relative activity, enzyme variant D9
-
-
?
bicyclo[4.2.0]octa-1,3,5-trien-7-amine + H2O + O2
bicyclo[4.2.0]octa-1,3,5-trien-7-one + NH3 + H2O2
12% relative activity, enzyme variant D9
-
-
?
butan-2-amine + H2O + O2
butan-2-one + NH3 + H2O2
67% relative activity, enzyme variant D9
-
-
?
heptan-2-amine + H2O + O2
heptan-2-one + NH3 + H2O2
87% relative activity, enzyme variant D9
-
-
?
N-methyl-1-phenylethan-1-amine + H2O + O2
1-phenylethan-1-one + methylamine + H2O2
14% relative activity, enzyme variant D9
-
-
?
1-(2-aminoethyl)pyrrolidine + H2O + O2
2,5,6,7-tetrahydro-3H-pyrrolo[1,2-a]imidazole + NH3 + H2O2
-
-
-
-
?
3-(2,3-dihydro-1H-indole-1-yl)propan-1-amine + H2O + O2
2,3,4,10-tetrahydropyrimido[1,2-a]indole + NH3 + H2O2
-
-
-
-
?
3-azabicyclo[3,3,0]octane + H2O + O2
3-azabicyclo-[3,3,0]oct-2-ene + NH3 + H2O2
-
-
-
-
?
dopamine + H2O + O2
(3,4-dihydroxyphenyl)acetaldehyde + NH3 + H2O2
-
-
-
?
serotonin + H2O + O2
(5-hydroxy-1H-indol-3-yl)acetaldehyde + NH3 + H2O2
-
-
-
?
1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
19% relative activity, enzyme variant D11
-
-
?
1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2
1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
92% relative activity, enzyme variant D9
-
-
?
additional information
?
-
the enzyme is used to successfully identify the alkaloid (+/-)-crispine A as a target for chemo-enzymatic deracemisation yielding the biologically active (R)-enantiomer in 97% enantiomeric excess
-
-
?
additional information
?
-
-
the enzyme is used to successfully identify the alkaloid (+/-)-crispine A as a target for chemo-enzymatic deracemisation yielding the biologically active (R)-enantiomer in 97% enantiomeric excess
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.12
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication
-
1.25
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication
-
1.42
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication
-
1.96
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/W430R, pH and temperature not specified in the publication
-
0.51
1,2,3,4-tetrahydronaphthalen-1-amine
pH 7.8, 30°C, enzyme variant D9
-
5.85
1,2,3,4-tetrahydronaphthalen-1-amine
pH 7.8, 30°C, variant D11
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.36
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/W430R, pH and temperature not specified in the publication
-
0.62
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication
-
0.77
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication
-
1.03
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication
-
0.342
1,2,3,4-tetrahydronaphthalen-1-amine
pH 7.8, 30°C, variant D11
-
0.491
1,2,3,4-tetrahydronaphthalen-1-amine
pH 7.8, 30°C, enzyme variant D9
-
2.882
2,3-dihydro-1H-inden-1-amine
pH 7.8, 30°C, enzyme variant D9
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.18
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/W430R, pH and temperature not specified in the publication
-
0.44
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication
-
0.62
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication
-
0.92
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline
mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication
-
0.058
1,2,3,4-tetrahydronaphthalen-1-amine
pH 7.8, 30°C, variant D11
-
0.963
1,2,3,4-tetrahydronaphthalen-1-amine
pH 7.8, 30°C, enzyme variant D9
-
1.958
2,3-dihydro-1H-inden-1-amine
pH 7.8, 30°C, enzyme variant D9
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.014
substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230I/W430R, pH and temperature not specified in the publication
0.016
substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230I/W430R, pH and temperature not specified in the publication
0.018
substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication
0.02
0.025
substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme T354S, pH and temperature not specified in the publication
0.03
substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication
0.04
substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230R/W430C, pH and temperature not specified in the publication
0.09
substrate: (S)-2-phenyl-pyrroline, mutant enzyme T354S, pH and temperature not specified in the publication
0.108
substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230R/W430C, pH and temperature not specified in the publication
0.13
substrate: (S)-2-phenyl-pyrroline, wild-type enzyme, pH and temperature not specified in the publication
0.22
substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230I/W430R, pH and temperature not specified in the publication
0.23
0.3
substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication
0.52
substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication
0.66
substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication
0.67
substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication
0.02
substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication
0.02
substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication
0.23
substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230R/W430C, pH and temperature not specified in the publication
0.23
substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). AOFN_ASPNG
495
0
55617
Swiss-Prot
other Location (Reliability: 1)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
T354S
LG-F-B5, no activity with 1,2,3,4-tetrahydro-1-phenylisoquinoline
W230I/T354S/W430R
LG-F-B7, the mutant enzyme accepts the bulky substrate 1,2,3,4-tetrahydro-1-phenylisoquinoline with a specific activity of 0.3 U/mg
W230I/T354S/W430R/M242R/Y365V
LG-J-B4, specific activity towards 1,2,3,4-tetrahydro-1-phenylisoquinoline is improved more than 2fold as compared to mutant enzyme W230I/T354S/W430R
W230I/W430R
LG-F-B6, mutations change the size and thus shape of the active site pocket so that 1,2,3,4-tetrahydro-1-phenylisoquinoline is accepted with notable activity
W230R/W430C
LG-F-G6, specific activity towards 1,2,3,4-tetrahydro-1-methylisoquinoline is improved 6fold by mutant enzyme W230R/W430C/C214L as compared to mutant enzyme W230R/W430C
W230R/W430C/C214L
LG-I-D11, specific activity towards 1,2,3,4-tetrahydro-1-methylisoquinoline is improved 6fold as compared to mutant enzyme W230R/W430C, it is also active with 1,2,3,4-tetrahydro-1-phenylisoquinoline. When deracemizing 1,2,3,4-tetrahydro-1-methylisoquinoline on a preparative scale, the MAO-N variant allows access to the (S)-enantiomer. It also shows good activity in the preparation of (S)-1,2,3,4-tetrahydro-1-ethylisoquinoline and (S)-1,2,3,4-tetrahydro-1-isopropylisoquinoline on a preparative scale
additional information
the variant D9 exhibits the highest activity for most substrates and is applied to the deracemisation of a comprehensive set of selected primary amines. In all cases, excellent enantioselectivity is achieved (enantiomeric excess is higher than 99%) with moderate to good yields (55-80%)
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21-Gold (DE3), BL21 Plyse, and BL21 Plysee cells
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
the enzyme is used to successfully identify the alkaloid (+/-)-crispine A as a target for chemo-enzymatic deracemisation yielding the biologically active (R)-enantiomer in 97% enantiomeric excess
synthesis
monoamine oxidase (MAO-N) is a synthetic tool for the enantioselective synthesis of chiral amines
synthesis
when deracemizing 1,2,3,4-tetrahydro-1-methylisoquinoline on a preparative scale, the MAO-N variant W230R/W430C/C214L allows access to the (S)-enantiomer. It also shows good activity in the preparation of (S)-1,2,3,4-tetrahydro-1-ethylisoquinoline and (S)-1,2,3,4-tetrahydro-1-isopropylisoquinoline on a preparative scale
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schilling, B.; Lerch, K.
Amine oxidases from Aspergillus niger: identification of a novel flavin-dependent enzyme
Biochim. Biophys. Acta
1243
529-537
1995
Aspergillus niger
Suzuki, H.; Ogura, Y.; Yamada, H.
Kinetic studies on the amine oxidase reaction
J. Biochem.
72
703-712
1972
Aspergillus niger
Bailey, K.R.; Ellis, A.J.; Reiss, R.; Snape, T.J.; Turner, N.J.
A template-based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (+/-)-crispine A
Chem. Commun. (Camb. )
2007
3640-3642
2007
Aspergillus niger (P46882), Aspergillus niger
Ramesh, H.; Woodley, J.
Process characterization of a monoamine oxidase
J. Mol. Catal. B
106
124-131
2014
Aspergillus niger
-
Rios-Solis, L.; Mothia, B.; Yi, S.; Zhou, Y.; Micheletti, M.; Lye, G.
High throughput screening of monoamine oxidase (MAO-N-D5) substrate selectivity and rapid kinetic model generation
J. Mol. Catal. B
120
100-110
2015
Aspergillus niger
-
Herter, S.; Medina, F.; Wagschal, S.; Benhaaim, C.; Leipold, F.; Turner, N.
Mapping the substrate scope of monoamine oxidase (MAO-N) as a synthetic tool for the enantioselective synthesis of chiral amines
Bioorg. Med. Chem.
26
1338-1346
2018
Aspergillus niger (P46882)
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