KEGG   ENZYME: 1.14.21.2Help
Entry
EC 1.14.21.2                Enzyme                                 

Name
(S)-cheilanthifoline synthase;
CYP719A14 (gene name);
(S)-scoulerine oxidase (methylenedioxy-bridge-forming) (ambiguous);
(S)-scoulerine,NADPH:oxygen oxidoreductase (methylenedioxy-bridge-forming) (ambiguous)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and the other dehydrogenated
BRITE hierarchy
Sysname
(S)-scoulerine,NADPH:oxygen oxidoreductase [(S)-cheilanthifoline-forming]
Reaction(IUBMB)
(S)-scoulerine + NADPH + H+ + O2 = (S)-cheilanthifoline + NADP+ + 2 H2O [RN:R03834]
Reaction(KEGG)
Substrate
(S)-scoulerine [CPD:C02106];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(S)-cheilanthifoline [CPD:C05174];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) enzyme 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 1.14.21.12, (S)-nandinine synthase, which catalyses a similar reaction at the other side of the (S)-scoulerine molecule, forming (S)-nandinine.
History
EC 1.14.21.2 created 1999 as EC 1.1.3.33, transferred 2002 to EC 1.14.21.2, modified 2016
Pathway
Isoquinoline alkaloid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K21070  
(S)-cheilanthifoline synthase
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 (1991) 2953-2961.
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 (2011) 186-93.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
138791-27-2

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