| Entry |
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| Name |
(R)-6-hydroxynicotine oxidase;
D-6-hydroxynicotine oxidase;
6-hydroxy-D-nicotine oxidase
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| Class |
Oxidoreductases;
Acting on the CH-NH group of donors;
With oxygen as acceptor
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| Sysname |
(R)-6-hydroxynicotine:oxygen oxidoreductase
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| 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]
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| Reaction(KEGG) |
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| 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]
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| 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]
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| 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).
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| History |
EC 1.5.3.6 created 1972, modified 2015
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| Pathway |
| Nicotinate and nicotinamide metabolism | | Microbial metabolism in diverse environments |
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| Orthology |
| (R)-6-hydroxynicotine oxidase |
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| Reference |
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| Authors |
Decker K, Bleeg H. |
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| Title |
Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans. |
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| Journal |
Biochim. Biophys. Acta. 105 (1965) 313-24. |
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| Reference |
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| Authors |
Bruhmuller M, Mohler H, Decker K. |
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| Title |
Covalently bound flavin in D-6-hydroxynicotine oxidase from Arthrobacter oxidans. Purification and properties of D-6-hydroxynicotine oxidase. |
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| Journal |
Eur. J. Biochem. 29 (1972) 143-51. |
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| Reference |
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| Authors |
Brandsch R, Hinkkanen AE, Mauch L, Nagursky H, Decker K |
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| Title |
6-Hydroxy-D-nicotine oxidase of Arthrobacter oxidans. Gene structure of the flavoenzyme and its relationship to 6-hydroxy-L-nicotine oxidase. |
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| Journal |
Eur. J. Biochem. 167 (1987) 315-20. |
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| Reference |
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| Authors |
Schenk S, Hoelz A, Krauss B, Decker K |
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| Title |
Gene structures and properties of enzymes of the plasmid-encoded nicotine catabolism of Arthrobacter nicotinovorans. |
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| Journal |
J. Mol. Biol. 284 (1998) 1323-39. |
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| Reference |
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| Authors |
Koetter JW, Schulz GE |
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| Title |
Crystal structure of 6-hydroxy-D-nicotine oxidase from Arthrobacter nicotinovorans. |
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| Journal |
J. Mol. Biol. 352 (2005) 418-28. |
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| Other DBs |
ExplorEnz - The Enzyme Database: IUBMB Enzyme Nomenclature: ExPASy - ENZYME nomenclature database: UM-BBD (Biocatalysis/Biodegradation Database): BRENDA, the Enzyme Database: CAS: 37233-46-8 |
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| LinkDB |
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