KEGG ENZYME: 1.5.3.6

ENZYME: 1.5.3.6

Entry

EC 1.5.3.6                  Enzyme

Name

(R)-6-hydroxynicotine oxidase;
D-6-hydroxynicotine oxidase;
6-hydroxy-D-nicotine oxidase

Class

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

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)

R07170 R11049 R11050

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

ec01100

Metabolic pathways

ec01120

Microbial metabolism in diverse environments

Orthology

K19890

(R)-6-hydroxynicotine oxidase

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)
DOI:10.1016/s0926-6593(65)80155-2

Reference

2 [PMID:4628374]

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

Eur J Biochem 29:143-51 (1972)
DOI:10.1111/j.1432-1033.1972.tb01968.x

Reference

3 [PMID:3622516]

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

Eur J Biochem 167:315-20 (1987)
DOI:10.1111/j.1432-1033.1987.tb13338.x

Reference

4 [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

5 [PMID:16095622]

Authors

Koetter JW, Schulz GE

Title

Crystal structure of 6-hydroxy-D-nicotine oxidase from Arthrobacter nicotinovorans.

Journal

J Mol Biol 352:418-28 (2005)
DOI:10.1016/j.jmb.2005.07.041

Other DBs

ExplorEnz - The Enzyme Database:

1.5.3.6

IUBMB Enzyme Nomenclature:

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

CAS:	37233-46-8

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