KEGG ENZYME: 1.5.99.4

KEGG

ENZYME: 1.5.99.4

Entry

EC 1.5.99.4                 Enzyme

Name

nicotine 6-hydroxylase;
nicotine oxidase;
D-nicotine oxidase;
nicotine:(acceptor) 6-oxidoreductase (hydroxylating);
L-nicotine oxidase;
nicotine dehydrogenase (incorrect)

Class

Oxidoreductases;
Acting on the CH-NH group of donors;
With unknown physiological acceptors

Sysname

nicotine:acceptor 6-oxidoreductase (hydroxylating)

Reaction(IUBMB)

(S)-nicotine + acceptor + H2O = (S)-6-hydroxynicotine + reduced acceptor [RN:R02860]

Reaction(KEGG)

R02860;
(other) R07946

Substrate

(S)-nicotine [CPD:C00745];
acceptor [CPD:C00028];
H2O [CPD:C00001]

Product

(S)-6-hydroxynicotine [CPD:C01056];
reduced acceptor [CPD:C00030]

Comment

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].

History

EC 1.5.99.4 created 1972, modified 2023

Pathway

Nicotinate and nicotinamide metabolism

Metabolic pathways

Microbial metabolism in diverse environments

Orthology

nicotine dehydrogenase subunit A

nicotine dehydrogenase subunit B

nicotine dehydrogenase subunit C

Genes

L3V59_37120 L3V59_37125 L3V59_37130

BGV:	CAL12_14715

ROP:	ROP_27550(ndhC) ROP_27560(ndhB) ROP_27570(ndhA)

ROA:	Pd630_LPD07481 Pd630_LPD07482 Pd630_LPD07483

RKO:	JWS14_44780

SGFS_017910 SGFS_017920 SGFS_017930

M4V62_06935

QR300_41530

QU709_39110 QU709_39115 QU709_39120

ARX:	ARZXY2_4539 ARZXY2_4541(coxL)

PNV:	JMY29_20695 JMY29_20700 JMY29_20705

TED:	U5C87_22500

NCA:	Noca_0594 Noca_0595 Noca_0596

OG417_33505

OHB01_11550

LWP59_09885

OG774_07250

DSM104299_03662(cdhA)

BRCON_2394

Reference

1 [PMID:13475371]

Authors

BEHRMAN EJ, STANIER RY.

Title

The bacterial oxidation of nicotinic acid.

Journal

J Biol Chem 228:923-45 (1957)

Reference

2 [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

3 [PMID:4962139]

Authors

Hochstein LI, Dalton BP.

Title

The purification and properties of nicotine oxidase.

Journal

Biochim Biophys Acta 139:56-68 (1967)
DOI:10.1016/0005-2744(67)90113-1

Reference

4 [PMID:13610912]

Authors

HOCHSTEIN LI, RITTENBERG SC.

Title

The bacterial oxidation of nicotine. II. The isolation of the first oxidative product and its identification as (1)-6-hydroxynicotine.

Journal

J Biol Chem 234:156-60 (1959)

Other DBs

ExplorEnz - The Enzyme Database:

IUBMB Enzyme Nomenclature:

ExPASy - ENZYME nomenclature database:

UM-BBD (Biocatalysis/Biodegradation Database):

BRENDA, the Enzyme Database:

CAS:	37256-31-8

DBGET integrated database retrieval system