Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 1.4.3.4 extracted from

  • Li, G.; Yao, P.; Gong, R.; Li, J.; Liu, P.; Lonsdale, R.; Wu, Q.; Lin, J.; Zhu, D.; Reetz, M.
    Simultaneous engineering of an enzymes entrance tunnel and active site The case of monoamine oxidase MAO-N (2017), Chem. Sci., 8, 4093-4099 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.4.3.4

Application

Application Comment Organism
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 Aspergillus niger

Protein Variants

Protein Variants Comment Organism
T354S LG-F-B5, no activity with 1,2,3,4-tetrahydro-1-phenylisoquinoline Aspergillus niger
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 Aspergillus niger
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 Aspergillus niger
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 Aspergillus niger
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 Aspergillus niger
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 Aspergillus niger

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.12
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication Aspergillus niger
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 Aspergillus niger
1.42
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication Aspergillus niger
1.96
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230I/W430R, pH and temperature not specified in the publication Aspergillus niger

Organism

Organism UniProt Comment Textmining
Aspergillus niger P46882
-
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
0.014
-
 substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230I/W430R, pH and temperature not specified in the publication Aspergillus niger
0.016
-
 substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230I/W430R, pH and temperature not specified in the publication Aspergillus niger
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 Aspergillus niger
0.02
-
 substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication Aspergillus niger
0.02
-
 substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication Aspergillus niger
0.025
-
 substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme T354S, pH and temperature not specified in the publication Aspergillus niger
0.03
-
 substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230I/T354S/W430R/M242R/Y365V, pH and temperature not specified in the publication Aspergillus niger
0.04
-
 substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230R/W430C, pH and temperature not specified in the publication Aspergillus niger
0.09
-
 substrate: (S)-2-phenyl-pyrroline, mutant enzyme T354S, pH and temperature not specified in the publication Aspergillus niger
0.108
-
 substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230R/W430C, pH and temperature not specified in the publication Aspergillus niger
0.13
-
 substrate: (S)-2-phenyl-pyrroline, wild-type enzyme, pH and temperature not specified in the publication Aspergillus niger
0.22
-
 substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230I/W430R, pH and temperature not specified in the publication Aspergillus niger
0.23
-
 substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230R/W430C, pH and temperature not specified in the publication Aspergillus niger
0.23
-
 substrate: (S)-2-phenyl-pyrroline, mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication Aspergillus niger
0.3
-
 substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication Aspergillus niger
0.52
-
 substrate: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline, mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication Aspergillus niger
0.66
-
 substrate: (S)-1,2,3,4-tetrahydro-1-methylisoquinoline, mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication Aspergillus niger
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 Aspergillus niger

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-1,2,3,4-tetrahydro-1-methylisoquinoline + H2O + O2
-
 Aspergillus niger ? + H2O2
-
 ?
1,2,3,4-tetrahydro-1-phenylisoquinoline + H2O + O2
-
 Aspergillus niger ? + H2O2
-
 ?
2-phenyl-pyrroline + H2O + O2
-
 Aspergillus niger ? + 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
0.36
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230I/W430R, pH and temperature not specified in the publication Aspergillus niger
0.62
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication Aspergillus niger
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 Aspergillus niger
1.03
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication Aspergillus niger

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.18
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230I/W430R, pH and temperature not specified in the publication Aspergillus niger
0.44
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230I/T354S/W430R, pH and temperature not specified in the publication Aspergillus niger
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 Aspergillus niger
0.92
-
 (S)-1,2,3,4-tetrahydro-1-methylisoquinoline mutant enzyme W230R/W430C/C214L, pH and temperature not specified in the publication Aspergillus niger