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show all sequences of 1.5.3.5

Mechanism of flavoprotein L-6-hydroxynicotine oxidase pH and solvent isotope effects and identification of key active site residues

Fitzpatrick, P.F.; Chadegani, F.; Zhang, S.; Dougherty, V.; Biochemistry 56, 869-875 (2017)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
expression in Escherichi coli
Paenarthrobacter nicotinovorans
Engineering
Amino acid exchange
Commentary
Organism
K287M
mutation results in an about 10-fold decreases in kcat/Km and k(red) for (S)-6-hydroxynicotine and a 6000-fold decrease in the kcat/Km value for oxygen
Paenarthrobacter nicotinovorans
N166A
mutation results in an about 30fold decrease in kcat/Km and k(red) for (S)-6-hydroxynicotine, respectively, with larger effects on the kcat/Km value for (S)-6-hydroxynornicotine. The shapes of the pH profiles are not altered
Paenarthrobacter nicotinovorans
Y311F
mutation results in an about 30fold decrease in kcat/Km and k(red) for (S)-6-hydroxynicotine, respectively, with larger effects on the kcat/Km value for (S)-6-hydroxynornicotine. The shapes of the pH profiles are not altered
Paenarthrobacter nicotinovorans
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.011
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme K287M
Paenarthrobacter nicotinovorans
0.064
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
0.13
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
0.19
-
O2
pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
0.2
-
O2
pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
0.2
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
0.29
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
0.34
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
0.46
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine
Paenarthrobacter nicotinovorans
1.1
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
1.2
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(S)-6-hydroxynicotine + H2O + O2
Paenarthrobacter nicotinovorans
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Paenarthrobacter nicotinovorans
-
-
-
Purification (Commentary)
Commentary
Organism
-
Paenarthrobacter nicotinovorans
Reaction
Reaction
Commentary
Organism
(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
Paenarthrobacter nicotinovorans
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(S)-6-hydroxynicotine + H2O + O2
-
741943
Paenarthrobacter nicotinovorans
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
741943
Paenarthrobacter nicotinovorans
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynornicotine + H2O + O2
-
741943
Paenarthrobacter nicotinovorans
?
-
-
-
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Paenarthrobacter nicotinovorans
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.26
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme K287M
Paenarthrobacter nicotinovorans
2.5
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
4.8
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
9.1
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
16
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
20.9
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
78
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Paenarthrobacter nicotinovorans
Cofactor
Cofactor
Commentary
Organism
Structure
FAD
flavoprotein
Paenarthrobacter nicotinovorans
Cloned(Commentary) (protein specific)
Commentary
Organism
expression in Escherichi coli
Paenarthrobacter nicotinovorans
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
FAD
flavoprotein
Paenarthrobacter nicotinovorans
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
K287M
mutation results in an about 10-fold decreases in kcat/Km and k(red) for (S)-6-hydroxynicotine and a 6000-fold decrease in the kcat/Km value for oxygen
Paenarthrobacter nicotinovorans
N166A
mutation results in an about 30fold decrease in kcat/Km and k(red) for (S)-6-hydroxynicotine, respectively, with larger effects on the kcat/Km value for (S)-6-hydroxynornicotine. The shapes of the pH profiles are not altered
Paenarthrobacter nicotinovorans
Y311F
mutation results in an about 30fold decrease in kcat/Km and k(red) for (S)-6-hydroxynicotine, respectively, with larger effects on the kcat/Km value for (S)-6-hydroxynornicotine. The shapes of the pH profiles are not altered
Paenarthrobacter nicotinovorans
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.011
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme K287M
Paenarthrobacter nicotinovorans
0.064
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
0.13
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
0.19
-
O2
pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
0.2
-
O2
pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
0.2
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
0.29
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
0.34
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
0.46
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine
Paenarthrobacter nicotinovorans
1.1
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
1.2
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(S)-6-hydroxynicotine + H2O + O2
Paenarthrobacter nicotinovorans
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
-
Paenarthrobacter nicotinovorans
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(S)-6-hydroxynicotine + H2O + O2
-
741943
Paenarthrobacter nicotinovorans
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynicotine + H2O + O2
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
741943
Paenarthrobacter nicotinovorans
1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
-
-
?
(S)-6-hydroxynornicotine + H2O + O2
-
741943
Paenarthrobacter nicotinovorans
?
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Paenarthrobacter nicotinovorans
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.26
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme K287M
Paenarthrobacter nicotinovorans
2.5
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
4.8
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
9.1
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
16
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
20.9
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
78
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8
-
assay at
Paenarthrobacter nicotinovorans
General Information
General Information
Commentary
Organism
metabolism
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
Paenarthrobacter nicotinovorans
General Information (protein specific)
General Information
Commentary
Organism
metabolism
the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine
Paenarthrobacter nicotinovorans
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.048
-
O2
pH 7.0, 25°C, mutant enzyme K287M, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
2
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
8.6
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
14
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
24
-
O2
pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
24
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme K287M
Paenarthrobacter nicotinovorans
103
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
110
-
O2
pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
150
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine
Paenarthrobacter nicotinovorans
270
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
370
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
600
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.048
-
O2
pH 7.0, 25°C, mutant enzyme K287M, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
2
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
8.6
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
14
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme N166A
Paenarthrobacter nicotinovorans
24
-
O2
pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
24
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme K287M
Paenarthrobacter nicotinovorans
103
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, mutant enzyme Y311F
Paenarthrobacter nicotinovorans
110
-
O2
pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
150
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine
Paenarthrobacter nicotinovorans
270
-
O2
pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine
Paenarthrobacter nicotinovorans
370
-
(S)-6-hydroxynornicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
600
-
(S)-6-hydroxynicotine
pH 7.0, 25°C, wild-type enzyme
Paenarthrobacter nicotinovorans
Other publictions for EC 1.5.3.5
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
741943
Fitzpatrick
Mechanism of flavoprotein L-6 ...
Paenarthrobacter nicotinovorans
Biochemistry
56
869-875
2017
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1
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3
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11
-
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1
-
1
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1
1
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3
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1
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7
1
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1
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1
1
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3
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11
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1
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1
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3
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1
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7
1
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-
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1
1
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12
12
741691
Yu
Molecular mechanism of nicoti ...
Ochrobactrum sp. SJY1
Appl. Environ. Microbiol.
81
272-281
2015
-
-
1
-
-
-
-
1
-
1
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1
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1
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1
-
-
-
-
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2
-
1
1
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1
1
1
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1
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1
1
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1
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1
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1
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1
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-
2
-
1
1
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1
1
1
-
-
-
-
-
-
-
-
741686
Qiu
A novel (S)-6-hydroxynicotine ...
Shinella sp.
Appl. Environ. Microbiol.
80
5552-5560
2014
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-
1
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-
7
2
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1
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1
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4
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1
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3
1
1
1
3
2
1
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3
1
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1
1
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7
-
2
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1
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1
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1
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3
1
1
1
3
2
1
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3
-
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1
1
-
2
2
718677
Wang
Identification of nicotine bio ...
Agrobacterium tumefaciens, Agrobacterium tumefaciens S33, Paenarthrobacter nicotinovorans
Appl. Microbiol. Biotechnol.
95
1567-1578
2012
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4
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4
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1
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7
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2
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4
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1
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7
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2
-
-
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2
-
-
-
-
2
2
-
-
-
726378
Kachalova
Crystallographic snapshots of ...
Paenarthrobacter nicotinovorans
Proc. Natl. Acad. Sci. USA
108
4800-4805
2011
-
-
-
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1
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2
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1
-
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4
-
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1
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1
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1
-
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2
-
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4
-
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-
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-
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-
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712752
Kachalova
Crystal structure analysis of ...
Paenarthrobacter nicotinovorans
J. Mol. Biol.
396
785-799
2010
-
-
1
1
-
-
1
1
-
-
-
1
-
2
-
1
-
-
-
-
-
-
2
1
-
-
-
-
-
-
-
1
1
-
-
-
-
1
1
1
-
-
-
1
1
1
-
-
-
1
-
-
1
-
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
1
1
-
-
-
700058
Ganas
Uptake of L-nicotine and of 6- ...
Paenarthrobacter nicotinovorans, Paenarthrobacter nicotinovorans PAO1
Microbiology
155
1866-1877
2009
-
-
1
-
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5
-
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2
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1
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-
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-
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2
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1
1
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392441
Schenk
Horizontal gene transfer invol ...
Paenarthrobacter nicotinovorans
J. Mol. Evol.
48
178-186
1999
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392430
Schenk
Gene structures and properties ...
Paenarthrobacter nicotinovorans
J. Mol. Biol.
284
1323-1339
1998
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392431
Grether-Beck
Structural analysis and molybd ...
Paenarthrobacter nicotinovorans
Mol. Microbiol.
13
929-936
1994
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392432
Pust
13C, 15N, and 31P NMR studies ...
Paenarthrobacter nicotinovorans
Biochemistry
28
516-521
1989
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392433
Brandsch
6-Hydroxy-D-nicotine oxidase o ...
Paenarthrobacter nicotinovorans
Eur. J. Biochem.
167
315-320
1987
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392434
Swafford
Localization of the enantiozym ...
Paenarthrobacter nicotinovorans
J. Bacteriol.
163
792-795
1985
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392435
Hinkkanen
Purification of the flavoprote ...
Paenarthrobacter nicotinovorans
Hoppe-Seyler's Z. Physiol. Chem.
364
801-806
1983
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392436
Decker
D- and L-6-hydroxynicotine oxi ...
Paenarthrobacter nicotinovorans
Z. Naturforsch. B
27
1072-1073
1972
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392437
Palmer
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Mechanisms of flavoprotein cat ...
Paenarthrobacter nicotinovorans
Biol. Oxidations (Singer, T. P. , ed. )
263-300
1968
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392438
Dai
Purification and properties of ...
Paenarthrobacter nicotinovorans
Eur. J. Biochem.
4
95-102
1968
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392439
Decker
Mechanism and specifcity of L- ...
Paenarthrobacter nicotinovorans
Eur. J. Biochem.
3
132-138
1967
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392440
Decker
Induction and purification of ...
Paenarthrobacter nicotinovorans
Biochim. Biophys. Acta
105
313-324
1965
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