IUBMB Enzyme Nomenclature

EC 1.5.99.4

Accepted name: nicotine 6-hydroxylase

Reaction: (S)-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor

For diagram of reacion, click here

Other name(s): nicotine oxidase; D-nicotine oxidase; nicotine:(acceptor) 6-oxidoreductase (hydroxylating); L-nicotine oxidase; nicotine dehydrogenase (incorrect)

Systematic name: nicotine:acceptor 6-oxidoreductase (hydroxylating)

Comments: A metalloprotein (FMN). The enzyme can act on both the naturally found (S)-enantiomer and the synthetic (R)-enantiomer of nicotine, with retention of configuration in both cases [4].

Links to other databases: BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 37256-31-8

References:

1. Behrman, E.J. and Stanier, R.Y. The bacterial oxidation of nicotinic acid. J. Biol. Chem. 228 (1957) 923-945. [PMID: 13475371]

2. Decker, K. and Bleeg, H. Induction and purification of stereospecific nicotine oxidizing enzymes from Arthrobacter oxidans. Biochim. Biophys. Acta 105 (1965) 313-324. [PMID: 5849820]

3. Hochstein, L.I. and Dalton, B.P. The purification and properties of nicotine oxidase. Biochim. Biophys. Acta 139 (1967) 56-68. [PMID: 4962139]

4. Hochstein, L.I. and Rittenberg, S.C. The bacterial oxidation of nicotine. II. The isolation of the first oxidative product and its identification as (1)-6-hydroxynicotine. J. Biol. Chem. 234 (1959) 156-160. [PMID: 13610912]

[EC 1.5.99.4 created 1972, modified 2023]


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