KEGG ENZYME: 1.14.13.178

ENZYME: 1.14.13.178

Entry

EC 1.14.13.178              Enzyme

Name

methylxanthine N1-demethylase;
ndmA (gene name)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

caffeine:oxygen oxidoreductase (N1-demethylating)

Reaction(IUBMB)

(1) caffeine + O2 + NAD(P)H + H+ = theobromine + NAD(P)+ + H2O + formaldehyde [RN:R07955 R07956];
(2) theophylline + O2 + NAD(P)H + H+ = 3-methylxanthine + NAD(P)+ + H2O + formaldehyde [RN:R07973 R07974];
(3) paraxanthine + O2 + NAD(P)H + H+ = 7-methylxanthine + NAD(P)+ + H2O + formaldehyde [RN:R07957 R07958]

Reaction(KEGG)

R07955 R07956 R07957 R07958 R07973 R07974;
(other) R07969 R07970

Substrate

caffeine [CPD:C07481];
O2 [CPD:C00007];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080];
theophylline [CPD:C07130];
paraxanthine [CPD:C13747]

Product

theobromine [CPD:C07480];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
formaldehyde [CPD:C00067];
3-methylxanthine [CPD:C16357];
7-methylxanthine [CPD:C16353]

Comment

A non-heme iron oxygenase. The enzyme from the bacterium Pseudomonas putida shares an NAD(P)H-FMN reductase subunit with EC 1.14.13.179, methylxanthine N3-demethylase, and has a 5-fold higher activity with NADH than with NADPH [2]. Also demethylate 1-methylxantine with lower efficiency. Forms part of the degradation pathway of methylxanthines.

History

EC 1.14.13.178 created 2013

Pathway

ec00232

Caffeine metabolism

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

ec01120

Microbial metabolism in diverse environments

Orthology

K21722

methylxanthine N1-demethylase

Genes

PCAF:

DSC91_007649

PYE:	A6J80_10900

PZH:	CX676_16200

ASZ:

ASN_2329

PARH:

I5S86_05095

IAM:	HC251_12390

Reference

1 [PMID:20966097]

Authors

Summers RM, Louie TM, Yu CL, Subramanian M

Title

Characterization of a broad-specificity non-haem iron N-demethylase from Pseudomonas putida CBB5 capable of utilizing several purine alkaloids as sole carbon and nitrogen source.

Journal

Microbiology 157:583-92 (2011)
DOI:10.1099/mic.0.043612-0

Sequence

[ag:AFD03116]

Reference

2 [PMID:22328667]

Authors

Summers RM, Louie TM, Yu CL, Gakhar L, Louie KC, Subramanian M

Title

Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids.

Journal

J Bacteriol 194:2041-9 (2012)
DOI:10.1128/JB.06637-11