KEGG ENZYME: 1.14.14.97

ENZYME: 1.14.14.97

Entry

EC 1.14.14.97               Enzyme

Name

methyltetrahydroprotoberberine 14-monooxygenase;
methyltetrahydroprotoberberine 14-hydroxylase;
(S)-cis-N-methyltetrahydroberberine 14-monooxygenase;
(S)-cis-N-methyltetrahydroprotoberberine-14-hydroxylase;
CYP82N4 (gene name);
(S)-N-methylcanadine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating);
(S)-cis-N-methylstylopine 14-hydroxylase

Class

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

Sysname

(S)-cis-N-methylcanadine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating)

Reaction(IUBMB)

(1) (S)-cis-N-methylcanadine + [reduced NADPH---hemoprotein reductase] + O2 = allocryptopine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R03842];
(2) (S)-cis-N-methylstylopine + [reduced NADPH---hemoprotein reductase] + O2 = protopine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R04700]

Reaction(KEGG)

R03842 R04700

Substrate

(S)-cis-N-methylcanadine [CPD:C02915];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
(S)-cis-N-methylstylopine [CPD:C06163]

Product

allocryptopine [CPD:C02134];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
protopine [CPD:C05189]

Comment

A cytochrome P-450 (heme-thiolate) protein involved in the biosynthesis of isoquinoline alkaloids in plants. It also hydroxylates (S)-cis-N-methyltetrahydrothalifendine, and (S)-cis-N-methyltetrahydropalmatine.

History

EC 1.14.14.97 created 1990 as EC 1.14.13.37, transferred 2018 to EC 1.14.14.97, modified 2023

Pathway

ec00950

Isoquinoline alkaloid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K21692

methyltetrahydroprotoberberine 14-monooxygenase

Genes

PSOM:

113322770

Reference

Authors

Rueffer, M. and Zenk, M.H.

Title

Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans.

Journal

Tetrahedron Lett 28:5307-5310 (1987)

Reference

2 [PMID:23313486]

Authors

Beaudoin GA, Facchini PJ

Title

Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis.

Journal

Biochem Biophys Res Commun 431:597-603 (2013)
DOI:10.1016/j.bbrc.2012.12.129

Sequence

[ag:AGC92398]

Other DBs

ExplorEnz - The Enzyme Database:

1.14.14.97

IUBMB Enzyme Nomenclature:

1.14.14.97

ExPASy - ENZYME nomenclature database:

1.14.14.97

BRENDA, the Enzyme Database:

1.14.14.97

CAS:	113478-42-5

DBGET integrated database retrieval system