Entry Name (S)-6-hydroxynicotine oxidase;
Class Oxidoreductases;BRITE hierarchy
Sysname (S)-6-hydroxynicotine:oxygen oxidoreductase
Reaction(IUBMB) (S)-6-hydroxynicotine + H2O + O2 = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2 (overall reaction) [RN:
R03202 ];
(1a) (S)-6-hydroxynicotine + O2 = 5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol + H2O2 [RN:
R11048 ];
(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 (S)-6-hydroxynicotine [CPD:
C01056 ];
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 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).
History EC 1.5.3.5 created 1972, modified 2015
Pathway ec00760 Nicotinate and nicotinamide metabolism
ec01120 Microbial metabolism in diverse environments
Orthology K19826 (S)-6-hydroxynicotine oxidase
Genes Taxonomy Reference Authors Decker K, Bleeg H.
Title Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans.
Journal Reference Authors Dai VD, Decker K, Sund H.
Title Purification and properties of L-6-hydroxynicotine 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 Qiu J, Wei Y, Ma Y, Wen R, Wen Y, Liu W
Title A novel (S)-6-hydroxynicotine oxidase gene from Shinella sp. strain HZN7.
Journal Other DBs ExplorEnz - The Enzyme Database: 1.5.3.5
ExPASy - ENZYME nomenclature database: 1.5.3.5
UM-BBD (Biocatalysis/Biodegradation Database): 1.5.3.5
BRENDA, the Enzyme Database: 1.5.3.5
