| EC |
1.4.2.2 |
| Accepted name: |
nicotine dehydrogenase |
| Reaction: |
(S)-nicotine + 2 ferricytochrome c = N-methylmyosmine + 2 ferrocytochrome c + 2 H+ |
| Glossary: |
(S)-nicotine = 3-[(S)-1-methylpyrrolidin-2-yl]pyridine
N-methylmyosamine = 3-(1-methyl-4,5-dihydro-1H-pyrrol-2-yl)pyridine |
| Other name(s): |
nicA2 (gene name) |
| Systematic name: |
(S)-nicotine:cytochrome c oxidoreductase (N-methylmimosine-forming) |
| Comments: |
The enzyme, characterized from the bacterium Pseudomonas putida S16, contains an FAD cofactor and belongs to the flavin-containing amine oxidase family. The enzyme from this bacterium is specific for the c-type cytochrome CycN. The product undergoes spontaneous hydrolysis to form pseudooxynicotine. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Tang, H., Wang, L., Wang, W., Yu, H., Zhang, K., Yao, Y. and Xu, P. Systematic unraveling of the unsolved pathway of nicotine degradation in Pseudomonas. PLoS Genet. 9:e1003923 (2013). [DOI] [PMID: 24204321] |
| 2. |
Dulchavsky, M., Clark, C.T., Bardwell, J.CA. and Stull, F. A cytochrome c is the natural electron acceptor for nicotine oxidoreductase. Nat. Chem. Biol. 17 (2021) 344–350. [DOI] [PMID: 33432238] |
|
| [EC 1.4.2.2 created 2022] |
| |
|
| |
|
| EC |
1.5.99.4 |
| Accepted name: |
nicotine 6-hydroxylase |
| Reaction: |
(S)-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor |
|
For diagram of nicotine catabolism by arthrobacter, 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. [DOI] [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] |
| |
|
| |
|
Printable version