IntEnz

EC 1.5.3.5 - (S)-6-hydroxynicotine oxidase

IntEnz Enzyme Nomenclature
EC 1.5.3.5

Names

Reactions

• (1) (S)-6-hydroxynicotine + H2O + O2 = 1-(6-hydroxypyridin-3-yl)-4-(methylamino)butan-1-one + H2O2
•   (1a) (S)-6-hydroxynicotine + O2 = 5-(N-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridin-2-ol + H2O2
•   (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)

Cofactor

• FAD

Comments:

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).

Links to other databases

References

1. Decker, K. and Bleeg, H.
   Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans.
   Biochim. Biophys. Acta 105 : 313-324 (1965). [PMID: 5849820]
2. Dai, V.D., Decker, K. and Sund, H.
   Purification and properties of L-6-hydroxynicotine oxidase.
   Eur. J. Biochem. 4 : 95-102 (1968). [PMID: 5646150]
3. Schenk, S., Hoelz, A., Krauss, B., Decker, K.
   Gene structures and properties of enzymes of the plasmid-encoded nicotine catabolism of Arthrobacter nicotinovorans.
   J. Mol. Biol. 284 : 1323-1339 (1998). [PMID: 9878353]
4. Qiu, J., Wei, Y., Ma, Y., Wen, R., Wen, Y., Liu, W.
   A novel (S)-6-hydroxynicotine oxidase gene from Shinella sp. strain HZN7.
   Appl. Environ. Microbiol. 80 : 5552-5560 (2014). [PMID: 25002425]

[EC 1.5.3.5 created 1972, modified 2015]