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Literature summary extracted from

  • Fitzpatrick, P.F.; Chadegani, F.; Zhang, S.; Dougherty, V.
    Mechanism of flavoprotein L-6-hydroxynicotine oxidase pH and solvent isotope effects and identification of key active site residues (2017), Biochemistry, 56, 869-875 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.5.3.5 expression in Escherichi coli Paenarthrobacter nicotinovorans

Protein Variants

EC Number Protein Variants Comment Organism
1.5.3.5 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
1.5.3.5 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
1.5.3.5 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]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.5.3.5 0.011
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme K287M Paenarthrobacter nicotinovorans
1.5.3.5 0.064
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, wild-type enzyme Paenarthrobacter nicotinovorans
1.5.3.5 0.13
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, wild-type enzyme Paenarthrobacter nicotinovorans
1.5.3.5 0.19
-
 O2 pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 0.2
-
 O2 pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 0.2
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme Y311F Paenarthrobacter nicotinovorans
1.5.3.5 0.29
-
 O2 pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 0.34
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme N166A Paenarthrobacter nicotinovorans
1.5.3.5 0.46
-
 O2 pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine Paenarthrobacter nicotinovorans
1.5.3.5 1.1
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, mutant enzyme Y311F Paenarthrobacter nicotinovorans
1.5.3.5 1.2
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, mutant enzyme N166A Paenarthrobacter nicotinovorans

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.5.3.5 (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

EC Number Organism UniProt Comment Textmining
1.5.3.5 Paenarthrobacter nicotinovorans
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.5.3.5
-
 Paenarthrobacter nicotinovorans

Reaction

EC Number Reaction Comment Organism Reaction ID
1.5.3.5 (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
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.5.3.5 (S)-6-hydroxynicotine + H2O + O2
-
 Paenarthrobacter nicotinovorans 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
 ?
1.5.3.5 (S)-6-hydroxynicotine + H2O + O2 the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine Paenarthrobacter nicotinovorans 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
-
 ?
1.5.3.5 (S)-6-hydroxynornicotine + H2O + O2
-
 Paenarthrobacter nicotinovorans ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.5.3.5 L-6-hydroxynicotine oxidase
-
 Paenarthrobacter nicotinovorans
1.5.3.5 LHNO
-
 Paenarthrobacter nicotinovorans

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.5.3.5 25
-
 assay at Paenarthrobacter nicotinovorans

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.5.3.5 0.26
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme K287M Paenarthrobacter nicotinovorans
1.5.3.5 2.5
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, mutant enzyme N166A Paenarthrobacter nicotinovorans
1.5.3.5 4.8
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme N166A Paenarthrobacter nicotinovorans
1.5.3.5 9.1
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, mutant enzyme Y311F Paenarthrobacter nicotinovorans
1.5.3.5 16
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, wild-type enzyme Paenarthrobacter nicotinovorans
1.5.3.5 20.9
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme Y311F Paenarthrobacter nicotinovorans
1.5.3.5 78
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, wild-type enzyme Paenarthrobacter nicotinovorans

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.5.3.5 8
-
 assay at Paenarthrobacter nicotinovorans

Cofactor

EC Number Cofactor Comment Organism Structure
1.5.3.5 FAD flavoprotein Paenarthrobacter nicotinovorans

General Information

EC Number General Information Comment Organism
1.5.3.5 metabolism the enzyme catalyzes the oxidation of (S)-6-hydroxynicotine to 6-hydroxypseudooxynicotine during microbial catabolism of nicotine Paenarthrobacter nicotinovorans

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.5.3.5 0.048
-
 O2 pH 7.0, 25°C, mutant enzyme K287M, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 2
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, mutant enzyme N166A Paenarthrobacter nicotinovorans
1.5.3.5 8.6
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, mutant enzyme Y311F Paenarthrobacter nicotinovorans
1.5.3.5 14
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme N166A Paenarthrobacter nicotinovorans
1.5.3.5 24
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme K287M Paenarthrobacter nicotinovorans
1.5.3.5 24
-
 O2 pH 7.0, 25°C, mutant enzyme N166A, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 103
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, mutant enzyme Y311F Paenarthrobacter nicotinovorans
1.5.3.5 110
-
 O2 pH 7.0, 25°C, mutant enzyme Y311F, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 150
-
 O2 pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynornicotine Paenarthrobacter nicotinovorans
1.5.3.5 270
-
 O2 pH 7.0, 25°C, wild-type enzyme, cosubstrate: (S)-6-hydroxynicotine Paenarthrobacter nicotinovorans
1.5.3.5 370
-
 (S)-6-hydroxynornicotine pH 7.0, 25°C, wild-type enzyme Paenarthrobacter nicotinovorans
1.5.3.5 600
-
 (S)-6-hydroxynicotine pH 7.0, 25°C, wild-type enzyme Paenarthrobacter nicotinovorans