Entry Name (R)-6-hydroxynicotine oxidase;
Class Oxidoreductases;BRITE hierarchy
Sysname (R)-6-hydroxynicotine:oxygen oxidoreductase
Reaction(IUBMB) (R)-6-hydroxynicotine + H2O + O2 = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2 (overall reaction) [RN:
R07170 ];
(1a) (R)-6-hydroxynicotine + O2 = 5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol + H2O2 [RN:
R11050 ];
(1b) 5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol + H2O = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one (spontaneous) [RN:
R11049 ]
Reaction(KEGG) Substrate (R)-6-hydroxynicotine [CPD:
C03043 ];
H2O [CPD:
C00001 ];
O2 [CPD:
C00007 ];
5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol [CPD:
C21075 ]
Product 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one [CPD:
C01297 ];
H2O2 [CPD:
C00027 ];
5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol [CPD:
C21075 ]
Comment A flavoprotein (FAD). The enzyme, which participates in nicotine degradation, is specific for (R) isomer of 6-hydroxynicotine, derived from the uncommon (R)-nicotine. The bacterium Arthrobacter nicotinovorans, in which this enzyme was originally discovered, has a different enzyme that catalyses a similar reaction with the (S)-isomer (cf. EC
1.5.3.5 , (S)-6-hydroxynicotine oxidase).
History EC 1.5.3.6 created 1972, modified 2015
Pathway ec00760 Nicotinate and nicotinamide metabolism
ec01120 Microbial metabolism in diverse environments
Orthology K19890 (R)-6-hydroxynicotine oxidase
Reference Authors Decker K, Bleeg H.
Title Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans.
Journal Reference Authors Bruhmuller M, Mohler H, Decker K.
Title Covalently bound flavin in D-6-hydroxynicotine oxidase from Arthrobacter oxidans. Purification and properties of D-6-hydroxynicotine oxidase.
Journal Reference Authors Brandsch R, Hinkkanen AE, Mauch L, Nagursky H, Decker K
Title 6-Hydroxy-D-nicotine oxidase of Arthrobacter oxidans. Gene structure of the flavoenzyme and its relationship to 6-hydroxy-L-nicotine oxidase.
Journal Reference Authors Schenk S, Hoelz A, Krauss B, Decker K
Title Gene structures and properties of enzymes of the plasmid-encoded nicotine catabolism of Arthrobacter nicotinovorans.
Journal Reference Authors Koetter JW, Schulz GE
Title Crystal structure of 6-hydroxy-D-nicotine oxidase from Arthrobacter nicotinovorans.
Journal Other DBs ExplorEnz - The Enzyme Database: 1.5.3.6
ExPASy - ENZYME nomenclature database: 1.5.3.6
UM-BBD (Biocatalysis/Biodegradation Database): 1.5.3.6
BRENDA, the Enzyme Database: 1.5.3.6
LinkDB All DBs
