KEGG   ORTHOLOGY: K21693
Entry
K21693                      KO                                     
Symbol
CYP82N2_3
Name
protopine 6-monooxygenase [EC:1.14.14.98]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Reaction
R04699  protopine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K21693  CYP82N2_3; protopine 6-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K21693  CYP82N2_3; protopine 6-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
    1.14.14.98  protopine 6-monooxygenase
     K21693  CYP82N2_3; protopine 6-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP82 family
   K21693  CYP82N2_3; protopine 6-monooxygenase
Other DBs
GO: 0047087
Genes
PSOM: 113330723 113357146
AG: AGC92397(CYP82N3) BAK20464(CYP82N2v2)
Reference
PMID:22421633 (CYP82N2)
  Authors
Takemura T, Ikezawa N, Iwasa K, Sato F
  Title
Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells.
  Journal
Phytochemistry 91:100-8 (2013)
DOI:10.1016/j.phytochem.2012.02.013
  Sequence
[ag:BAK20464]
Reference
PMID:23313486 (CYP82N3)
  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:AGC92397]
LinkDB

KEGG   ENZYME: 1.14.14.98
Entry
EC 1.14.14.98               Enzyme                                 
Name
protopine 6-monooxygenase;
protopine 6-hydroxylase;
CYP82N2 (gene name)
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
protopine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
protopine + [reduced NADPH---hemoprotein reductase] + O2 = 6-hydroxyprotopine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R04699]
Reaction(KEGG)
R04699
Substrate
protopine [CPD:C05189];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
6-hydroxyprotopine [CPD:C05190];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein involved in benzophenanthridine alkaloid synthesis in higher plants.
History
EC 1.14.14.98 created 1999 as EC 1.14.13.55, transferred 2018 to EC 1.14.14.98
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K21693  protopine 6-monooxygenase
Genes
PSOM: 113330723 113357146
Reference
1
  Authors
Tanahashi T, Zenk MH.
  Title
Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis.
  Journal
Phytochemistry 29:1113-1122 (1990)
Reference
2  [PMID:22421633]
  Authors
Takemura T, Ikezawa N, Iwasa K, Sato F
  Title
Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells.
  Journal
Phytochemistry 91:100-8 (2013)
DOI:10.1016/j.phytochem.2012.02.013
  Sequence
[ag:BAK20464]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.98
IUBMB Enzyme Nomenclature: 1.14.14.98
ExPASy - ENZYME nomenclature database: 1.14.14.98
BRENDA, the Enzyme Database: 1.14.14.98
CAS: 128561-60-4
LinkDB

KEGG   REACTION: R04699
Entry
R04699                      Reaction                               
Name
protopine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
Definition
Protopine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 6-Hydroxyprotopine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C05189 + C03024 + C00007 <=> C05190 + C03161 + C00001
Reaction class
RC01203  C05189_C05190
Enzyme
1.14.14.98
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
    1.14.14.98
     R04699  Protopine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 6-Hydroxyprotopine + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K21693  protopine 6-monooxygenase [EC:1.14.14.98]
Other DBs
RHEA: 22647
LinkDB

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