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. and Zenk, M.H.
  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

  All links  
Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical substance (6)   
   KEGG COMPOUND (6)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
Gene (5)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (4)   
Protein sequence (4)   
   UniProt (2)   
   SWISS-PROT (2)   
Protein domain (4)   
   InterPro (4)   
All databases (28)   

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