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hypotaurine + H2O + NAD+ = taurine + NADH + H+
a molybdohemoprotein
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O

ordered ter-bi mechanism with an irreversible step between the second and third substrate, NADPH is added first, followed by O2 and the oxidizable organic substrate last
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
reaction mechanism of S-oxygenation of N-substituted thioureas
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
reaction mechanism of S-oxygenation of N-substituted thioureas
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic reaction mechanism via 4alpha-hydroperoxyflavin transient intermediate
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic reaction mechanism, structure-function relationship, FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, the first step for FMO is reduction of the FAD by NADPH, the next step is formation of a C4a-hydroperoxy flavin by addition of molecular oxygen to the reduced FAD, when the substrate is accepted by FMO the enzyme is already in an active form, the protein environment of FMO apparently protects the hydroperoxy flavin from decomposing, conserving NADPH, and affording an effcient two-electron oxygenating agent for nucleophiles with the appropriate size and shape
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism and structure-function relationship, overview
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism via C4a-hydroperoxyflavin intermediate and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH in presence of O2
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism via C4a-hydroperoxyflavin intermediate and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
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(R)-metamphetamine + NADPH + H+ + O2
(R)-metamphetamine N-oxide + NADP+ + H2O
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substrate of isoform FMO1
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?
(S)-metamphetamine + NADPH + H+ + O2
(S)-metamphetamine N-oxide + NADP+ + H2O
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substrate of isoforms FMO1 and FMO3
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-
?
(S)-nicotine + NADPH + H+ + O2
?
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-
-
-
?
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
(S)-nicotine N-1'-oxygenation
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-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
1,2-dimethylhydrazine + NADPH + H+ + O2
1,2-dimethylhydrazine N-oxide + NADP+ + H2O
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-
-
-
r
1,2-dimethylhydrazine + NADPH + O2
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
1-butanethiol + NADPH + O2
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
1-methyl-2-benzylhydrazine + NADPH + H+ + O2
1-methyl-2-benzylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
1-methyl-2-benzylhydrazine + NADPH + O2
?
1-methyl-2-thioimidazole + NADPH + O2
?
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?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
1-methyl-6,7-dihydroxytetrahydroisoquinoline + NADPH + O2
?
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-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazine + NADPH + H+ + O2
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazine N-oxide + NADP+ + H2O
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r
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
10-([N,N-dimethylaminopentyl]-2-trifluoromethyl)phenothiazine + NADPH + O2
?
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?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine + NADPH + H+ + O2
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine N-oxide + NADP+ + H2O
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?
10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine + NADPH + O2
?
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i.e. 5-DPT or diethylenetriaminepentaacetic acid
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?
2 bicyclo[4.2.0]octan-7-one + 2 NADH + 2 H+ + 2 O2
(3aS,7aS)-hexahydro-1-benzofuran-2(3H)-one + (3aR,7aS)-hexahydro-2-benzofuran-1(3H)-one + 2 NAD+ + 2 H2O
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?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
2-acetylsulfanylmethyl-4-(4-methoxyphenyl)-4-oxobutyric acid + NADPH + H+ + O2
?
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-
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?
2-chlorophenol + O2
chlorohydroquinone + H2O
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
2-mercaptobenzimidazole + NADPH + O2
?
2-[(methylsulfanyl)methyl]furan + NADPH + H+ + O2
2-[(methylsulfanyl)methyl]furan S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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?
2-[2-(4-methoxyphenyl)-2-oxoethyl]-acrylic acid + NADPH + H+ + O2
?
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a synthetic 10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl)phenothiazine analogue
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?
3-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-3-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 15% R-enantiomer as product
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-
?
3-hydroxy-nabumetone + NADPH + H+ + O2
? + NADP+ + H2O
activation reaction
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?
4-(4-methoxyphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
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FMO1, poor activity with FMO3 and FMO5
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?
4-(4-methylphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
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FMO1 and FMO5, no activity with FMO3
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?
4-(methylsulfanyl)benzonitrile + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)benzonitrile S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 22% S-enantiomer as product
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-
?
4-(methylsulfanyl)phenol + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)phenol S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 81% S-enantiomer as product
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?
4-aminobenzoic acid hydrazide + NADPH + O2
?
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?
4-chlorophenol + O2
hydroquinone + H2O + Cl-
4-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-4-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 95% S-enantiomer as product
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?
5,6-dimethylxanthenone-4-acetic acid + NADPH + H+ + O2
?
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substrate of isoform FMO3, methyl hydroxylation
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?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
9-hydroxy-5,6-dimethyl-N-(2-(dimethylamino)ethyl)-6H-pyrido(4,3-B)-carbazole-1-carboxamide + NADPH + H+ + O2
2-(9-hydroxy-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamido)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
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substrate of isoform FMO3
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-
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
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substrate of isoform FMO3
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-
?
aldicarb + NADPH + O2
?
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?
almotriptan + NADPH + H+ + O2
almotriptan N-oxide + NADP+ + H2O
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substrate of isoform FMO3
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-
?
alpha-naphthylthiourea + NADPH + O2
?
aminopyrine + NADPH + O2
?
ammonia + NADPH + H+ + O2
? + NADP+ + H2O
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-
?
amphetamine + NADPH + H+ + O2
?
amphetamine + NADPH + H+ + O2
amphetamine N-oxide + NADP+ + H2O
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substrate of isoform FMO3
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
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?
benzydamine + NADPH + H+ + O2
?
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i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
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-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
benzylhydrazine + NADPH + H+ + O2
benzylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
benzylhydrazine + NADPH + O2
?
beta-ethylphenylhydrazine + NADPH + H+ + O2
beta-ethylphenylhydrazine N-oxide + NADP+ + H2O
-
-
-
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r
beta-ethylphenylhydrazine + NADPH + O2
?
bicyclo[3.2.0]hept-2-en-6-one + NADH + H+ + O2
?
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
-
-
-
-
?
bupivacaine + NADPH + O2
bupivacaine-oxide + NADP+
-
-
-
-
?
butyl ethyl sulfide + NADPH + H+ + O2
butyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butyl methyl sulfide + NADPH + H+ + O2
butyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butylhydrazine + NADPH + H+ + O2
butylhydrazine N-oxide + NADP+ + H2O
-
-
-
-
r
butylhydrazine + NADPH + O2
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
chlorpromazine + NADPH + H+ + O2
chlorpromazine oxide + NADP+ + H2O
-
-
-
-
?
chlorpromazine + NADPH + O2
?
chlorpromazine + NADPH + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O