KEGG   ENZYME: 1.5.3.5Help
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
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
ROP: ROP_27530
ROA: Pd630_LPD07478
NCA: Noca_0586
Taxonomy
Reference
1  [PMID:5849820]
  Authors
Decker K, Bleeg H.
  Title
Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans.
  Journal
Biochim Biophys Acta 105:313-24 (1965)
Reference
2  [PMID:5646150]
  Authors
Dai VD, Decker K, Sund H.
  Title
Purification and properties of L-6-hydroxynicotine oxidase.
  Journal
Eur J Biochem 4:95-102 (1968)
DOI:10.1111/j.1432-1033.1968.tb00177.x
Reference
3  [PMID:9878353]
  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
J Mol Biol 284:1323-39 (1998)
DOI:10.1006/jmbi.1998.2227
Reference
4  [PMID:25002425]
  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
Appl Environ Microbiol 80:5552-60 (2014)
DOI:10.1128/AEM.01312-14
Other DBs
ExplorEnz - The Enzyme Database: 1.5.3.5
IUBMB Enzyme Nomenclature: 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
CAS: 37256-29-4

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