KEGG   ORTHOLOGY: K21692
Entry
K21692                      KO                                     
Symbol
CYP82N4
Name
methyltetrahydroprotoberberine 14-monooxygenase [EC:1.14.14.97]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Reaction
R03842  (S)-cis-N-methylcanadine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating)
R04700  (S)-cis-N-methylstylopine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K21692  CYP82N4; methyltetrahydroprotoberberine 14-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K21692  CYP82N4; methyltetrahydroprotoberberine 14-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.97  methyltetrahydroprotoberberine 14-monooxygenase
     K21692  CYP82N4; methyltetrahydroprotoberberine 14-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP82 family
   K21692  CYP82N4; methyltetrahydroprotoberberine 14-monooxygenase
Other DBs
GO: 0047084
Genes
PSOM: 113322770
AG: AGC92398(CYP82N4)
Reference
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]
LinkDB

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
LinkDB

KEGG   REACTION: R04700
Entry
R04700                      Reaction                               
Name
(S)-cis-N-methylstylopine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating)
Definition
(S)-cis-N-Methylstylopine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Protopine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C06163 + C03024 + C00007 <=> C05189 + C03161 + C00001
Reaction class
RC01007  C05189_C06163
Enzyme
1.14.14.97
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.97
     R04700  (S)-cis-N-Methylstylopine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Protopine + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K21692  methyltetrahydroprotoberberine 14-monooxygenase [EC:1.14.14.97]
LinkDB

DBGET integrated database retrieval system