KEGG ENZYME: 1.5.3.5

ENZYME: 1.5.3.5

Entry

EC 1.5.3.5                  Enzyme

Name

(S)-6-hydroxynicotine oxidase;
L-6-hydroxynicotine oxidase;
6-hydroxy-L-nicotine oxidase;
6-hydroxy-L-nicotine:oxygen oxidoreductase;
nctB (gene name)

Class

Oxidoreductases;
Acting on the CH-NH group of donors;
With oxygen as acceptor

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)

R03202 R11048 R11049

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

ec01100

Metabolic pathways

ec01120

Microbial metabolism in diverse environments

Orthology

K19826

(S)-6-hydroxynicotine oxidase