IntEnz

EC 1.5.99.4 - Nicotine dehydrogenase

IntEnz Enzyme Nomenclature
EC 1.5.99.4

Names

Reactions

• 14769 [IUBMB]
  (S)-nicotine

  (S)-nicotine

  Name origin: UniProt - CHECKED (C)

  CHEBI:59806

  Formula: C10H15N2
  Charge: 1

  ChEBI compound status: CHECKED (C)

  

  +

  A

  A

  Name origin: UniProt - CHECKED (C)

  CHEBI:13193

  Formula: R
  Charge: 0

  ChEBI compound status: CHECKED (C)

  

  +

  H₂O

  H2O

  Name origin: UniProt - CHECKED (C)

  CHEBI:15377

  Formula: H2O
  Charge: 0

  ChEBI compound status: CHECKED (C)

  

  =

  (S)-6-hydroxynicotine

  (S)-6-hydroxynicotine

  Name origin: UniProt - CHECKED (C)

  CHEBI:58182

  Formula: C10H15N2O
  Charge: 1

  ChEBI compound status: CHECKED (C)

  

  +

  AH₂

  AH2

  Name origin: UniProt - CHECKED (C)

  CHEBI:17499

  Formula: H2R
  Charge: 0

  ChEBI compound status: CHECKED (C)

  
• 42352
  (R)-nicotine

  (R)-nicotine

  Name origin: UniProt - CHECKED (C)

  CHEBI:79008

  Formula: C10H15N2
  Charge: 1

  ChEBI compound status: CHECKED (C)

  

  +

  A

  A

  Name origin: UniProt - CHECKED (C)

  CHEBI:13193

  Formula: R
  Charge: 0

  ChEBI compound status: CHECKED (C)

  

  +

  H₂O

  H2O

  Name origin: UniProt - CHECKED (C)

  CHEBI:15377

  Formula: H2O
  Charge: 0

  ChEBI compound status: CHECKED (C)

  

  =

  (R)-6-hydroxynicotine

  (R)-6-hydroxynicotine

  Name origin: UniProt - CHECKED (C)

  CHEBI:58413

  Formula: C10H15N2O
  Charge: 1

  ChEBI compound status: CHECKED (C)

  

  +

  AH₂

  AH2

  Name origin: UniProt - CHECKED (C)

  CHEBI:17499

  Formula: H2R
  Charge: 0

  ChEBI compound status: CHECKED (C)

  

Cofactor

• FMN

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

References

1. Behrman, E.J. and Stanier, R.Y.
   The bacterial oxidation of nicotinic acid.
   J. Biol. Chem. 228: 923-945 (1957). [PMID: 13475371]
2. 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]
3. Hochstein, L.I. and Dalton, B.P.
   The purification and properties of nicotine oxidase.
   Biochim. Biophys. Acta 139: 56-68 (1967). [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: 156-160 (1959). [PMID: 13610912]

[EC 1.5.99.4 created 1972]