KEGG   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
1
  Authors
Rueffer M, Zenk MH.
  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
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