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Literature summary for 1.4.3.4 extracted from

  • 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 (2018), Bioorg. Med. Chem., 26, 1338-1346 .
    View publication on PubMed
Search for more literature for 1.4.3.4

Application

Application Comment Organism
synthesis monoamine oxidase (MAO-N) is a synthetic tool for the enantioselective synthesis of chiral amines Aspergillus niger

Protein Variants

Protein Variants Comment Organism
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%) Aspergillus niger

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.51
-
 1,2,3,4-tetrahydronaphthalen-1-amine pH 7.8, 30°C, enzyme variant D9 Aspergillus niger
1.47
-
 2,3-dihydro-1H-inden-1-amine pH 7.8, 30°C, enzyme variant D9 Aspergillus niger
5.85
-
 1,2,3,4-tetrahydronaphthalen-1-amine pH 7.8, 30°C, variant D11 Aspergillus niger
7.06
-
 2,3-dihydro-1H-inden-1-amine pH 7.8, 30°C, variant D11 Aspergillus niger

Organism

Organism UniProt Comment Textmining
Aspergillus niger P46882
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(1E)-1-phenylhexa-1,5-dien-3-amine + H2O + O2 3% relative activity, enzyme variant D9 Aspergillus niger -1-phenylhexa-1,5-dien-3-one + NH3 + H2O2
-
 ?
1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 19% relative activity, enzyme variant D11 Aspergillus niger 1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 92% relative activity, enzyme variant D9 Aspergillus niger 1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
1-(2,4-difluorophenyl)ethan-1-amine + H2O + O2 148% relative activity, enzyme variant D9 Aspergillus niger 1-(2,4-difluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2,6-difluorophenyl)ethan-1-amine + H2O + O2 48% relative activity, enzyme variant D9 Aspergillus niger 1-(2,6-difluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2-bromo-4-fluorophenyl)ethan-1-amine + H2O + O2 28% relative activity, enzyme variant D9 Aspergillus niger 1-(2-bromo-4-fluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2-chloro-4-fluorophenyl)ethan-1-amine + H2O + O2 96% relative activity, enzyme variant D9 Aspergillus niger 1-(2-chloro-4-fluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2-chlorophenyl)ethan-1-amine + H2O + O2 19% relative activity, enzyme variant D9 Aspergillus niger 1-(2-chlorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2-fluorophenyl)ethan-1-amine + H2O + O2 175% relative activity, enzyme variant D9 Aspergillus niger 1-(2-fluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2-fluorophenyl)propan-2-amine + H2O + O2 16% relative activity, enzyme variant D9 Aspergillus niger 1-(2-fluorophenyl)propan-2-one + NH3 + H2O2
-
 ?
1-(2-methoxyphenyl)ethan-1-amine + H2O + O2 59% relative activity, enzyme variant D9 Aspergillus niger 1-(2-methoxyphenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(2-methylphenyl)ethan-1-amine + H2O + O2 23% relative activity, enzyme variant D9 Aspergillus niger 1-(2-methylphenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(3,5-difluorophenyl)ethan-1-amine + H2O + O2 8% relative activity, enzyme variant D9 Aspergillus niger 1-(3,5-difluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(3-fluorophenyl)ethan-1-amine + H2O + O2 30% relative activity, enzyme variant D9 Aspergillus niger 1-(3-fluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(3-methylphenyl)but-3-en-1-amine + H2O + O2 9% relative activity, enzyme variant D9 Aspergillus niger 1-(3-methylphenyl)but-3-en-1-one + NH3 + H2O2
-
 ?
1-(4-bromo-3-fluorophenyl)but-3-en-1-amine + H2O + O2 16% relative activity, enzyme variant D9 Aspergillus niger 1-(4-bromo-3-fluorophenyl)but-3-en-1-one + NH3 + H2O2
-
 ?
1-(4-bromophenyl)ethan-1-amine + H2O + O2 147% relative activity, enzyme variant D9 Aspergillus niger 1-(4-bromophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-chlorophenyl)but-3-en-1-amine + H2O + O2 20% relative activity, enzyme variant D9 Aspergillus niger 1-(4-chlorophenyl)but-3-en-1-one + NH3 + H2O2
-
 ?
1-(4-chlorophenyl)ethan-1-amine + H2O + O2 246% relative activity, enzyme variant D9 Aspergillus niger 1-(4-chlorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-fluoro-2-methylphenyl)ethan-1-amine + H2O + O2 19% relative activity, enzyme variant D9 Aspergillus niger 1-(4-fluoro-2-methylphenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-fluoro-3-methylphenyl)ethan-1-amine + H2O + O2 74% relative activity, enzyme variant D9 Aspergillus niger 1-(4-fluoro-3-methylphenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-fluorophenyl)ethan-1-amine + H2O + O2 123% relative activity, enzyme variant D9 Aspergillus niger 1-(4-fluorophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-iodophenyl)ethan-1-amine + H2O + O2 39% relative activity, enzyme variant D9 Aspergillus niger 1-(4-iodophenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-methoxyphenyl)ethan-1-amine + H2O + O2 111% relative activity, enzyme variant D9 Aspergillus niger 1-(4-methoxyphenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(4-methylphenyl)ethan-1-amine + H2O + O2 211% relative activity, enzyme variant D9 Aspergillus niger 1-(4-methylphenyl)ethan-1-one + NH3 + H2O2
-
 ?
1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-amine + H2O + O2 18% relative activity, enzyme variant D9 Aspergillus niger 1-(5,6,7,8-tetrahydrynaphthalen-2-yl)ethan-1-one + NH3 + H2O2
-
 ?
1-(6-methoxynaphthalen-2-yl)ethan-1-amine + H2O + O2 4% relative activity, enzyme variant D9 Aspergillus niger 1-(6-methoxynaphthalen-2-yl)ethan-1-one + NH3 + H2O2
-
 ?
1-(adamantan-1-yl)ethan-1-amine + H2O + O2 50% relative activity, enzyme variant D9 Aspergillus niger 1-(adamantan-1-yl)ethan-1-one + NH3 + H2O2
-
 ?
1-(furan-2-yl)ethan-1-amine + H2O + O2 9% relative activity, enzyme variant D9 Aspergillus niger 1-(furan-2-yl)ethan-1-one + NH3 + H2O2
-
 ?
1-(naphthalen-2-yl)but-3-en-1-amine + H2O + O2 22% relative activity, enzyme variant D9 Aspergillus niger 1-(naphthalen-2-yl)but-3-en-1-one + NH3 + H2O2
-
 ?
1-(pyridin-4-yl)but-3-en-1-amine + H2O + O2 28% relative activity, enzyme variant D9 Aspergillus niger 1-(pyridin-4-yl)but-3-en-1-one + NH3 + H2O2
-
 ?
1-(pyrimidin-4-yl)ethan-1-amine + H2O + O2 11% relative activity, enzyme variant D9 Aspergillus niger 1-(pyrimidin-4-yl)ethan-1-one + NH3 + H2O2
-
 ?
1-(thiophen-2-yl)ethan-1-amine + H2O + O2 10% relative activity, enzyme variant D9 Aspergillus niger 1-(thiophen-2-yl)ethan-1-one + NH3 + H2O2
-
 ?
1-cyclohexylethan-1-amine + H2O + O2 202% relative activity, enzyme variant D9 Aspergillus niger 1-cyclohexylethan-1-one + NH3 + H2O2
-
 ?
1-cyclopropyl-1-(4-fluorophenyl)methanamine + H2O + O2 184% relative activity, enzyme variant D9 Aspergillus niger cyclopropyl(4-fluorophenyl)methanone + NH3 + H2O2
-
 ?
1-phenylbut-3-en-1-amine + H2O + O2 5% relative activity, enzyme variant D9 Aspergillus niger 1-phenylbut-3-en-1-one + NH3 + H2O2
-
 ?
1-phenylethan-1-amine + H2O + O2 100% relative activity, enzyme variant D9 Aspergillus niger 1-phenylethan-1-one + NH3 + H2O2
-
 ?
1-phenylpropan-1-amine + H2O + O2 34% relative activity, enzyme variant D9 Aspergillus niger 1-phenylpropan-1-one + NH3 + H2O2
-
 ?
1-phenylpropan-2-amine + H2O + O2 22% relative activity, enzyme variant D9 Aspergillus niger 1-phenylpropan-2-one+ NH3 + H2O2
-
 ?
1-[4-(trifluoromethyl)phenyl]ethan-1-amine + H2O + O2 125% relative activity, enzyme variant D9 Aspergillus niger 1-(4-trifluoromethylphenyl)ethan-1-one + NH3 + H2O2
-
 ?
2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-1-amine + H2O + O2 12% relative activity, enzyme variant D9 Aspergillus niger 2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-1-one + NH3 + H2O2
-
 ?
2,3-dihydro-1H-inden-1-amine + H2O + O2 199% relative activity, enzyme variant D9 Aspergillus niger 2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
2,3-dihydro-1H-inden-1-one + NH3 + H2O2 165% relative activity, enzyme variant D11 Aspergillus niger 2,3-dihydro-1H-inden-1-amine + H2O + O2
-
 ?
2-methyl-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 4% relative activity, enzyme variant D9 Aspergillus niger 2-methyl-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
3,4-dihydro-2H-1-benzopyran-4-amine + H2O + O2 22% relative activity, enzyme variant D9 Aspergillus niger 2,3-dihydro-4H-1-benzopyran-4-one + NH3 + H2O2
-
 ?
4-bromo-2,3-dihydro-1H-inden-1-amine + H2O + O2 4% relative activity, enzyme variant D9 Aspergillus niger 4-bromo-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
4-chloro-2,3-dihydro-1H-inden-1-amine + H2O + O2 3% relative activity, enzyme variant D9 Aspergillus niger 4-chloro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
4-fluoro-2,3-dihydro-1H-inden-1-amine + H2O + O2 101% relative activity, enzyme variant D9 Aspergillus niger 4-fluoro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
4-methyl-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 5% relative activity, enzyme variant D9 Aspergillus niger 4-methyl-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
4-methylpentan-2-amine + H2O + O2 69% relative activity, enzyme variant D9 Aspergillus niger 4-methylpentan-2-one + NH3 + H2O2
-
 ?
5,6-dihydro-4H-cyclopenta[b]thiophen-4-amine + H2O + O2 33% relative activity, enzyme variant D9 Aspergillus niger 6-dihydro-4H-cyclopenta[b]thiophen-4-one + NH3 + H2O2
-
 ?
5-amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile + H2O + O2 103% relative activity, enzyme variant D9 Aspergillus niger 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile + NH3 + H2O2
-
 ?
5-fluoro-2,3-dihydro-1H-inden-1-amine + H2O + O2 242% relative activity, enzyme variant D9 Aspergillus niger 5-fluoro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
5-methyl-2,3-dihydro-1H-inden-1-amine + H2O + O2 61% relative activity, enzyme variant D9 Aspergillus niger 5-methyl-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
5-methyl-4,5,6,7-tetrahydro-1-benzofuran-4-amine + H2O + O2 214% relative activity, enzyme variant D9 Aspergillus niger 5-methyl-4,5,6,7-tetrahydro-1-benzofuran-4-one + NH3 + H2O2
-
 ?
5-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulene + H2O + O2 6% relative activity, enzyme variant D9 Aspergillus niger 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one + methylamine + H2O2
-
 ?
6-chloro-2,3-dihydro-1H-inden-1-amine + H2O + O2 103% relative activity, enzyme variant D9 Aspergillus niger 6-chloro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
6-fluoro-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 155% relative activity, enzyme variant D9 Aspergillus niger 6-fluoro-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
6-fluoro-2,3-dihydro-1H-inden-1-amine + H2O + O2 143% relative activity, enzyme variant D9 Aspergillus niger 6-fluoro-2,3-dihydro-1H-inden-1-one + NH3 + H2O2
-
 ?
6-methoxy-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 49% relative activity, enzyme variant D9 Aspergillus niger 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
6-methylhept-1-en-4-amine + H2O + O2 27% relative activity, enzyme variant D9 Aspergillus niger 6-methylhept-1-en-4-one + NH3 + H2O2
-
 ?
7-fluoro-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 90% relative activity, enzyme variant D9 Aspergillus niger 7-fluoro-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
7-methyl-1,2,3,4-tetrahydronaphthalen-1-amine + H2O + O2 39% relative activity, enzyme variant D9 Aspergillus niger 7-methyl-1,2,3,4-tetrahydronaphthalen-1-one + NH3 + H2O2
-
 ?
7-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-amine + H2O + O2 14% relative activity, enzyme variant D9 Aspergillus niger 7-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one + NH3 + H2O2
-
 ?
bicyclo[4.2.0]octa-1,3,5-trien-7-amine + H2O + O2 12% relative activity, enzyme variant D9 Aspergillus niger bicyclo[4.2.0]octa-1,3,5-trien-7-one + NH3 + H2O2
-
 ?
butan-2-amine + H2O + O2 67% relative activity, enzyme variant D9 Aspergillus niger butan-2-one + NH3 + H2O2
-
 ?
heptan-2-amine + H2O + O2 87% relative activity, enzyme variant D9 Aspergillus niger heptan-2-one + NH3 + H2O2
-
 ?
N-methyl-1-phenylethan-1-amine + H2O + O2 14% relative activity, enzyme variant D9 Aspergillus niger 1-phenylethan-1-one + methylamine + H2O2
-
 ?

Synonyms

Synonyms Comment Organism
MAO-N
-
 Aspergillus niger
monoamine oxidase N
-
 Aspergillus niger

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.342
-
 1,2,3,4-tetrahydronaphthalen-1-amine pH 7.8, 30°C, variant D11 Aspergillus niger
0.491
-
 1,2,3,4-tetrahydronaphthalen-1-amine pH 7.8, 30°C, enzyme variant D9 Aspergillus niger
1.213
-
 2,3-dihydro-1H-inden-1-amine pH 7.8, 30°C, variant D11 Aspergillus niger
2.882
-
 2,3-dihydro-1H-inden-1-amine pH 7.8, 30°C, enzyme variant D9 Aspergillus niger

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.058
-
 1,2,3,4-tetrahydronaphthalen-1-amine pH 7.8, 30°C, variant D11 Aspergillus niger
0.172
-
 2,3-dihydro-1H-inden-1-amine pH 7.8, 30°C, variant D11 Aspergillus niger
0.963
-
 1,2,3,4-tetrahydronaphthalen-1-amine pH 7.8, 30°C, enzyme variant D9 Aspergillus niger
1.958
-
 2,3-dihydro-1H-inden-1-amine pH 7.8, 30°C, enzyme variant D9 Aspergillus niger