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1.14.13.8: flavin-containing monooxygenase

This is an abbreviated version!
For detailed information about flavin-containing monooxygenase, go to the full flat file.

Word Map on EC 1.14.13.8

Reaction

Hypotaurine
+
H2O
 +
NAD+
=
taurine
 +
NADH
 +
H+

Synonyms

class 3 flavin-containing mono-oxygenase, class 3 FMO, dechlorinating flavin-dependent monooxygenase, dimethylaniline monooxygenase (N-oxide-forming), dimethylaniline monooxygenase [N-oxide-forming] 1, dimethylaniline N-oxidase, dimethylaniline oxidase, dimethylsulfone monooxygenase, DMA oxidase, EC 1.13.12.11, EC 1.8.1.3, EtaA, FAD-containing monooxygenase, FAD-containing monooxygenase 3, flavin containing monooxygenase 3, flavin mono-oxygenase, flavin monooxygenase, flavin-containing mono-oxygenase, flavin-containing monooxygenase, flavin-containing monooxygenase 1, flavin-containing monooxygenase 3, flavin-containing monooxygenase 5, flavin-containing monooxygenase-3, flavin-containing-monooxygenase, flavin-dependent monooxygenase, flavoprotein monooxygenase, FMO, FMO 1A1, FMO 1B1, FMO 1C1, FMO 1D1, FMO 1E1, FMO-E, FMO-I, FMO-II, FMO1, FMO2, FMO2.1, FMO3, FMO4, FMO5, FMOGS-OX6, FMOGS-OX7, HadA, hFMO1, hFMO3, hFMO5, Met S-oxidase, mFMO, mixed-function amine oxidase, monooxygenase FMO1, More, MymA, N,N-dimethylaniline monooxygenase, oxygenase, dimethylaniline mono- (N-oxide-forming), oxygenase, methylphenyltetrahydropyridine N-mono-, PtFMO, sfnG, TetX, type II flavin-containing monooxygenase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.13.8 flavin-containing monooxygenase

Engineering

Engineering on EC 1.14.13.8 - flavin-containing monooxygenase

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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A52T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
C530L
naturally occuring single nucleotide polymorphism of FMO2
D132H
D198E
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
D227K
pKa value 7.3 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
D36G
naturally occuring single nucleotide polymorphism of FMO2
down
-
FMO5 is downregulated in type II diabetes in liver. FMO1 downregulation and inhibition by 3,3'-diindolylmethane
E132H
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
E132H/E158K
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
E158K/E308G
E158K/T201K/E308G
-
naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
E158K/V257M
-
the naturally occuring polymorphisms reduce the oxidation and clearance of FMO3 substrates such as tyramine, and TMA in vitro, and mutations are highly likely to eliminate the enzyme function in vivo
E305X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E314G
naturally occuring single nucleotide polymorphism of FMO2
E314X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E32K
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
E339Q
naturally occuring single nucleotide polymorphism of FMO4
E362Q
naturally occuring single nucleotide polymorphism of FMO3
F182S
naturally occuring single nucleotide polymorphism of FMO2
F510X
-
natural genetic variant of isozyme FMO2, substrate specificity, overview
F69Y
naturally occuring single nucleotide polymorphism of FMO2
F81S
naturally occuring single nucleotide polymorphism of FMO2
G148X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
G180V
naturally occuring single nucleotide polymorphism of FMO3, the mutant is similar to the wild-type enzyme
G182E
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
G475D
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
G503R
naturally occuring single nucleotide polymorphism of FMO3
H360P
-
site-directed mutagenesis of isozyme FMO1, the mutant shows altered thermal stability and highly increased activity with mercaptoimidazole and chlorpromazine compared to the wild-type FMO1
I199T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
I303T
I303V
I468M
naturally occuring single nucleotide polymorphism of FMO3
K158L
-
Km-value for fenthion is 1.4fold higher than the wild-type value, Vmax for fenthion is nearly identical to the wild-type value, mutant of FMO3
K158L/D132H
-
Km-value for fenthion is 1.5fold higher than the wild-type value, Vmax for fenthion is 1.5fold higher than the wild-type value, mutant of FMO3
K416N
L360A
-
site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360H
-
site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
L360P
L360Q
-
site-directed mutagenesis of isozyme FMO3, the mutant shows altered thermal stability and reduced activity with mercaptoimidazole, chlorpromazine, and 10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine compared to the wild-type FMO3
M260V
naturally occuring single nucleotide polymorphism of FMO3
M434I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
M82T
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
N114S
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
N413K
P153L
P457L
naturally occuring single nucleotide polymorphism of FMO4
Q170K
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
Q206H
pKa value 6.5 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
Q470X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
Q472X
R205C
R223Q
R238P
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R238Q
naturally occuring single nucleotide polymorphism of FMO2
R249X
naturally occuring single nucleotide polymorphism of FMO2, probably inactive mutant
R378L
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R391T
naturally occuring single nucleotide polymorphism of FMO2
R492W
-
naturally occuring mutation involved in trimethylaminuria, the mutant fails to incorporate/retain the FAD cofactor
R500X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
R502V
-
no activity with methimazole, KM-value for methyl p-tolyl sulfide is 70% of the wild-type value, Vmax with methyl p-tolyl sulfide is 70% of the wild-type value, KM-value for imipramine is is nearly identical to the the wild-type value, Vmax with imipramine is 49% of the wild-type value, KM-value for fenthion is 88% of the wild-type value, Vmax with fenthion is 55% of wild-type value, mutant of FMO1
R502X
R506S
naturally occuring single nucleotide polymorphism of FMO4
R51G
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
S195L
T201K
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
T308S
naturally occuring single nucleotide polymorphism of FMO4
V143E
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
V257M
V257M/E308G
-
naturally occuring polymorphism, the substitutions do not affect enzyme activity in vitro
V257M/M260V
-
naturally occuring genetic variant of isozyme FMO3, and site-directed mutagenesis, the mutant shows reduced activity with sulindac and methyl 4-toyl sulfide compared to the wild-type FMO3
V277A
naturally occuring single nucleotide polymorphism of FMO3
V323A
naturally occuring single nucleotide polymorphism of FMO4
V58I
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
W388X
naturally occuring mutation causing trimethylaminuria or fish-odor-syndrome
Y228H
pKa value 7.9 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 6.9 for wild-type
E158A/E159A
-
the mutant shows similar activity with trimethylamine compared to the wild-type enzyme
Y207S
mutant exhibits very little indoxyl producing activity but the NADPH oxidase activity of the mutant is higher than that of the wild-type enzyme
E158A/E159A
-
the mutant shows similar activity with trimethylamine compared to the wild-type enzyme
-
Y207S
-
mutant exhibits very little indoxyl producing activity but the NADPH oxidase activity of the mutant is higher than that of the wild-type enzyme
-
C78A
-
site-directed mutagenesis, the mutation leads to an increase in KM and kcat compared to wild-type enzyme, but the mutant shows reduced activity compared to wild-type enzyme
C78I
-
site-directed mutagenesis, the mutation leads to an increase in KM and kcat compared to wild-type enzyme, but the mutant shows reduced activity compared to wild-type enzyme
C78L
-
site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
C78V
-
site-directed mutagenesis, the mutation leads to an increase in KM and kcat compared to wild-type enzyme, but the mutant shows reduced activity compared to wild-type enzyme
M15L/S23A
-
site-directed mutagenesis, combining the two mutations at the N-terminus results in a 3°C increase in apparent melting temperature. Both M15L and S23A are far from the active site and no significant effect on the kinetic parameters of the enzyme is observed. Adding more stabilizing mutations does not contribute to a higher thermostability
W319A
-
site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
W319F
-
site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
W47A
-
insoluble inactive protein
W47F
-
soluble and active protein. The spectrum of the flavin displays a redshift, the kcat values for NADPH, trimethylamine, and methimazole, show a 5-8fold decrease, and primary kinetic isotope effect values are higher than in wild-type. Mutant displays reduced flexibility in active site residues and, in particular, the nicotinamide moiety of NADP+
Y207W
Y207W/W319A
-
site-directed mutagenesis, the mutant shows reduced activity compared to wild-type enzyme
W47A
-
insoluble inactive protein
-
W47F
-
soluble and active protein. The spectrum of the flavin displays a redshift, the kcat values for NADPH, trimethylamine, and methimazole, show a 5-8fold decrease, and primary kinetic isotope effect values are higher than in wild-type. Mutant displays reduced flexibility in active site residues and, in particular, the nicotinamide moiety of NADP+
-
H228Y
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 7.7 for wild-type
K227D
pKa value 6.6 for N-oxygenation of 10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene, compared with 7.7 for wild-type
additional information