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Information on EC 1.5.3.5 - (S)-6-hydroxynicotine oxidase
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EC Tree
1.5.3.5 (S)-6-hydroxynicotine oxidaseIUBMB Comments
A flavoprotein (FAD). The enzyme, which participates in nicotine degradation, is specific for the (S) isomer of 6-hydroxynicotine. The bacterium Arthrobacter nicotinovorans, in which this enzyme was originally discovered, has a different enzyme that catalyses a similar reaction with the less common (R)-isomer (cf. EC 1.5.3.6, (R)-6-hydroxynicotine oxidase).
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Word Map
- 1.5.3.5
- arthrobacter
- 6-hydroxy-d-nicotine
- nicotinovorans
- oxidans
- flavin
- fad
-
flavoenzyme
-
nicotine-degrading
-
monoamine
- flavoproteins
-
hydride
- 6-hydroxypseudooxynicotine
-
dehydrogenation
- pseudooxynicotine
-
d-specific
- pyrrolidine
-
dithionite-reduced
-
carbon-carbon
-
self-formed
-
fad-binding
-
s-nicotine
-
l-enantiomer
-
fitzpatrick
-
carbon-nitrogen
- isoalloxazine
- 6-hdno
-
substrate-reduced
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
nica2, 6-hydroxy-l-nicotine oxidase, 6-hlno, 6hlno, l-6-hydroxynicotine oxidase, flavoprotein nicotine oxidoreductase, (s)-6-hydroxynicotine oxidase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
6-hydroxy-L-nicotine oxidase
6-hydroxy-L-nicotine:oxygen oxidoreductase
-
-
-
-
6HLNO
flavoprotein nicotine oxidoreductase
L-6-hydroxynicotine oxidase
NdpB
NicA2
6-hydroxy-L-nicotine oxidase
-
-
-
-
L-6-hydroxynicotine oxidase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-6-hydroxynicotine + H2O + O2 = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
(S)-6-hydroxynicotine + O2 = 5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol + H2O2
(1a)
-
-
-
5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol + H2O = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one
(1b), spontaneous
-
-
-
(S)-6-hydroxynicotine + H2O + O2 = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
overall reaction
-
-
-
(S)-6-hydroxynicotine + H2O + O2 = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
mechanism and roles of active site residues: Asn166 and Tyr311 bind the substrate, while Lys287 forms a water-mediated hydrogen bond with flavin N5
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(S)-6-hydroxynicotine:oxygen oxidoreductase
A flavoprotein (FAD). The enzyme, which participates in nicotine degradation, is specific for the (S) isomer of 6-hydroxynicotine. The bacterium Arthrobacter nicotinovorans, in which this enzyme was originally discovered, has a different enzyme that catalyses a similar reaction with the less common (R)-isomer (cf. EC 1.5.3.6, (R)-6-hydroxynicotine oxidase).
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CAS REGISTRY NUMBER
COMMENTARY
37256-29-4
-
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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
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
2-phenylethylamine + H2O + O2
2-phenylethanal + NH3 + H2O2
-
-
-
-
?
6-hydroxy-L-nicotine + H2O + O2
6-hydroxy-N-methylmyosmine + NH3 + H2O2
-
-
-
-
?
L-6-hydroxy-nor-nicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-aminobutan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
the enzyme is involved in degradation of nicotine
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
absolute stereospecificity on the L-form
intermediate product 6-hydroxy-N-methylmyosmine, which hydrolyzes to 6-hydroxy-pseudooxynicotine
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
the enzyme is essential for nicotine or (S)-6-hydroxynicotine degradation
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
the enzyme converts (S)-6-hydroxynicotine into 6-hydroxy-N-methylmyosmine which then spontaneously hydrolyzes into 6-hydroxypseudooxynicotine. (S)-6-Hydroxynicotine is the preferred substrate in vivo. The enzyme shows no activities toward the R enantiomer of nicotine or 6-hydroxynicotine
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
6-hydroxy-pseudooxynicotine + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
6-hydroxy-pseudooxynicotine + H2O2
-
-
-
-
?
(S)-nicotine + H2O + O2
N-methylmyosmine + H2O2
-
-
-
?
(S)-nicotine + H2O + O2
N-methylmyosmine + H2O2
N-methyl-myosmine, which is nonenzymatically hydrolyzed to pseudooxynicotine. The flavoenzyme preferentially oxidizes tertiary amines with an efficient reductive half-reaction and a very slow oxidative half-reaction when O2 is the oxidizing substrate, suggesting that the true oxidizing agent is unknown
-
-
?
(S)-nicotine + H2O + O2
N-methylmyosmine + H2O2
N-methyl-myosmine, which is nonenzymatically hydrolyzed to pseudooxynicotine. The flavoenzyme preferentially oxidizes tertiary amines with an efficient reductive half-reaction and a very slow oxidative half-reaction when O2 is the oxidizing substrate, suggesting that the true oxidizing agent is unknown
-
-
?
(S)-nicotine + H2O + O2
N-methylmyosmine + H2O2
the enzyme converts (S)-nicotine into N-methylmyosmine, which spontaneously hydrolyzes into pseudooxynicotine
-
-
?
additional information
?
-
-
transformation of 6-hydroxy-L-nicotine to 6-hydroxy-N-methylmyosmine, 6-hydroxypseudooxynicotine formation, overview
-
-
?
additional information
?
-
-
measurement of enzyme activity using dichlorindophenol. 6-Hydroxypseudooxynicotine forms from 6-hydroxy-N-methylmyosmine non-enzymatically
-
-
?
additional information
?
-
-
transformation of 6-hydroxy-L-nicotine to 6-hydroxy-N-methylmyosmine, 6-hydroxypseudooxynicotine formation, overview
-
-
?
additional information
?
-
-
measurement of enzyme activity using dichlorindophenol. 6-Hydroxypseudooxynicotine forms from 6-hydroxy-N-methylmyosmine non-enzymatically
-
-
?
additional information
?
-
-
also oxidizes circular secondary and tertiary amines
-
-
?
additional information
?
-
-
enzyme production is induced by growing cells in D,L-nicotine as only source of carbon and nitrogen
-
-
?
additional information
?
-
-
enzyme production is induced by growing cells in D,L-nicotine as only source of carbon and nitrogen
-
-
?
additional information
?
-
-
enzyme production is induced by growing cells in D,L-nicotine as only source of carbon and nitrogen
-
-
?
additional information
?
-
-
it is synthesized only during the logarithmic and stationary phases of growth
-
-
?
additional information
?
-
-
no activity with 6-hydroxy-D-nicotine
-
-
?
additional information
?
-
-
synthesis of 6-hydroxy-N-methylmyosmine and 6-hydroxy-pseudooxynicotine from 6-hydroxy-L-nicotine. 6-Hydroxypseudooxynicotine forms from 6-hydroxy-N-methylmyosmine non-enzymatically
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
6-hydroxy-L-nicotine + H2O + O2
6-hydroxy-N-methylmyosmine + NH3 + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyrid-3-yl)-4-(methylamino)-butan-1-one + H2O2
-
-
transitional product is 6-hydroxy-N-methylmyosmine that hydrolyses spontaneously
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
the enzyme is involved in degradation of nicotine
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
absolute stereospecificity on the L-form
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
-
-
?
(S)-6-hydroxynicotine + H2O + O2
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
the enzyme is essential for nicotine or (S)-6-hydroxynicotine degradation
-
-
?
additional information
?
-
-
transformation of 6-hydroxy-L-nicotine to 6-hydroxy-N-methylmyosmine, 6-hydroxypseudooxynicotine formation, overview
-
-
?
additional information
?
-
-
transformation of 6-hydroxy-L-nicotine to 6-hydroxy-N-methylmyosmine, 6-hydroxypseudooxynicotine formation, overview
-
-
?
additional information
?
-
-
enzyme production is induced by growing cells in D,L-nicotine as only source of carbon and nitrogen
-
-
?
additional information
?
-
-
enzyme production is induced by growing cells in D,L-nicotine as only source of carbon and nitrogen
-
-
?
additional information
?
-
-
enzyme production is induced by growing cells in D,L-nicotine as only source of carbon and nitrogen
-
-
?
additional information
?
-
-
it is synthesized only during the logarithmic and stationary phases of growth
-
-
?
additional information
?
-
-
no activity with 6-hydroxy-D-nicotine
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
1 FAD per subunit, non-covalently bound
FAD
binding domain structure, overview. The flavin may have a role in oxygen activation involving replacement of the water molecule by oxygen and superoxide formation
FAD
flavoprotein. FAD content is determined to be 1.0 of FAD per mole subunit
FAD
the FAD content of freshly prepared wild type enzyme averages 0.17 mol FAD per mol enzyme. The FAD content of MBP-tagged enzyme averages 0.8 mol FAD per mol of enzyme
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
the reaction progresses without the participation of metal ions
additional information
the enzyme does not require Al3+, Ca2+, Mg2+, or Mn2+ for its activity
additional information
-
the enzyme does not require Al3+, Ca2+, Mg2+, or Mn2+ for its activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
p-chloromercuriphenylsulfonate
-
60% inhibition at 0.025 mM, inhibition can be reversed by an excess of thiol compounds
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.011
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme K287M
0.02
(S)-6-hydroxynicotine
pH and temperature not specified in the publication
0.2
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme Y311F
0.34
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme N166A
2.7
(S)-6-hydroxynicotine
mutant R274A/Y311W/C417W, pH 7.4, 22°C
0.064
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, wild-type enzyme
1.1
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, mutant enzyme Y311F
1.2
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, mutant enzyme N166A
0.000114
(S)-nicotine
pH and temperature not specified in the publication
13
(S)-nicotine
mutant R274A/Y311W/C417W, pH 7.4, 37°C
16
(S)-nicotine
mutant R274A/Y311W/C417W, pH 7.4, 22°C
0.19
O2
-
pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine
0.2
O2
-
pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine
0.29
O2
-
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine
0.46
O2
-
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.26
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme K287M
2.5
(S)-6-hydroxynicotine
mutant R274A/Y311W/C417W, pH 7.4, 22°C
4.8
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme N166A
20.9
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme Y311F
2.5
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, mutant enzyme N166A
9.1
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, mutant enzyme Y311F
1.14
(S)-nicotine
mutant R274A/Y311W/C417W, pH 7.4, 37°C
2.65
(S)-nicotine
mutant R274A/Y311W/C417W, pH 7.4, 22°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
9.26
(S)-6-hydroxynicotine
mutant R274A/Y311W/C417W, pH 7.4, 22°C
103
(S)-6-hydroxynicotine
-
pH 7.0, 25°C, mutant enzyme Y311F
2
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, mutant enzyme N166A
8.6
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, mutant enzyme Y311F
370
(S)-6-hydroxynornicotine
-
pH 7.0, 25°C, wild-type enzyme
0.0204
(S)-nicotine
mutant R274A/Y311W/C417W, pH 7.4, 22°C
0.0877
(S)-nicotine
mutant R274A/Y311W/C417W, pH 7.4, 37°C
0.048
O2
-
pH 7.0, 25°C, mutant enzyme K287M, cosubstrate: (S)-6-hydroxynicotine
24
O2
-
pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine
110
O2
-
pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine
150
O2
-
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine
270
O2
-
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
(R)-6-hydroxynicotine
pH and temperature not specified in the publication