KEGG   ORTHOLOGY: K21070
Entry
K21070                      KO                                     
Symbol
CYP719A14
Name
(S)-cheilanthifoline synthase [EC:1.14.19.65]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Reaction
R03834  (S)-scoulerine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase [(S)-cheilanthifoline-forming]
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K21070  CYP719A14; (S)-cheilanthifoline synthase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K21070  CYP719A14; (S)-cheilanthifoline synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.19  With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
    1.14.19.65  (S)-cheilanthifoline synthase
     K21070  CYP719A14; (S)-cheilanthifoline synthase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP719 family
   K21070  CYP719A14; (S)-cheilanthifoline synthase
Other DBs
GO: 0047053
Genes
PSOM: 113347886 113349389 113349486
AG: ABR14722(CYP719A14)
Reference
PMID:21094631
  Authors
Diaz Chavez ML, Rolf M, Gesell A, Kutchan TM
  Title
Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana.
  Journal
Arch Biochem Biophys 507:186-93 (2011)
DOI:10.1016/j.abb.2010.11.016
  Sequence
[ag:ABR14722]
LinkDB

KEGG   ENZYME: 1.14.19.65
Entry
EC 1.14.19.65               Enzyme                                 
Name
(S)-cheilanthifoline synthase;
CYP719A14 (gene name);
(S)-scoulerine oxidase (methylenedioxy-bridge-forming) (ambiguous)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
Sysname
(S)-scoulerine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase [(S)-cheilanthifoline-forming]
Reaction(IUBMB)
(S)-scoulerine + [reduced NADPH---hemoprotein reductase] + O2 = (S)-cheilanthifoline + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R03834]
Reaction(KEGG)
R03834
Substrate
(S)-scoulerine [CPD:C02106];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(S)-cheilanthifoline [CPD:C05174];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein catalysing an oxidative reaction that does not incorporate oxygen into the product. Forms the methylenedioxy bridge of the protoberberine alkaloid cheilanthifoline by the oxidative ring closure of adjacent phenolic and methoxy groups of scoulerine. cf. EC 1.14.19.73, (S)-nandinine synthase, which catalyses a similar reaction at the other side of the (S)-scoulerine molecule, forming (S)-nandinine.
History
EC 1.14.19.65 created 1999 as EC 1.1.3.33, transferred 2002 to EC 1.14.21.2, modified 2016, transferred 2018 to EC 1.14.19.65
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K21070  (S)-cheilanthifoline synthase
Genes
PSOM: 113347886 113349389 113349486
Reference
1
  Authors
Bauer W, Zenk MH.
  Title
Two methylenedioxy bridge-forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis.
  Journal
Phytochemistry 30:2953-2961 (1991)
Reference
2  [PMID:21094631]
  Authors
Diaz Chavez ML, Rolf M, Gesell A, Kutchan TM
  Title
Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana.
  Journal
Arch Biochem Biophys 507:186-93 (2011)
DOI:10.1016/j.abb.2010.11.016
  Sequence
[ag:ABR14722]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.65
IUBMB Enzyme Nomenclature: 1.14.19.65
ExPASy - ENZYME nomenclature database: 1.14.19.65
BRENDA, the Enzyme Database: 1.14.19.65
CAS: 138791-27-2
LinkDB

KEGG   REACTION: R03834
Entry
R03834                      Reaction                               
Name
(S)-scoulerine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase [(S)-cheilanthifoline-forming]
Definition
(S)-Scoulerine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (S)-Cheilanthifoline + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Equation
C02106 + C03024 + C00007 <=> C05174 + C03161 + 2 C00001
Reaction class
RC00925  C02106_C05174
Enzyme
1.14.19.65
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
   1.14.19  With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
    1.14.19.65
     R03834  (S)-Scoulerine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (S)-Cheilanthifoline + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Orthology
K21070  (S)-cheilanthifoline synthase [EC:1.14.19.65]
Other DBs
RHEA: 20488
LinkDB

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