KEGG   ENZYME: 1.14.19.64
Entry
EC 1.14.19.64               Enzyme                                 
Name
(S)-stylopine synthase;
(S)-cheilanthifoline oxidase (methylenedioxy-bridge-forming)
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)-cheilanthifoline,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)
Reaction(IUBMB)
(S)-cheilanthifoline + [reduced NADPH---hemoprotein reductase] + O2 = (S)-stylopine + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R04690]
Reaction(KEGG)
R04690
Substrate
(S)-cheilanthifoline [CPD:C05174];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(S)-stylopine [CPD:C05175];
[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 second methylenedioxy bridge of the protoberberine alkaloid stylopine from oxidative ring closure of adjacent phenolic and methoxy groups of cheilanthifoline.
History
EC 1.14.19.64 created 1999 as EC 1.1.3.32, transferred 2002 to EC 1.14.21.1, transferred 2018 to EC 1.14.19.64
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13395  (S)-stylopine/(S)-canadine/(S)-nandinine synthase
Genes
NNU: 104604446
PSOM: 113322097 113347890
MSIN: 131224026 131255012 131255027 131255031 131255053 131255539 131258159 131258160 131258162 131258168 131258169 131258172 131258174
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)
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.64
IUBMB Enzyme Nomenclature: 1.14.19.64
ExPASy - ENZYME nomenclature database: 1.14.19.64
BRENDA, the Enzyme Database: 1.14.19.64
CAS: 138791-29-4

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Pathway (8)   
   KEGG PATHWAY (6)   
   KEGG MODULE (2)   
Chemical substance (6)   
   KEGG COMPOUND (6)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
Gene (22)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (21)   
Protein sequence (6)   
   UniProt (3)   
   SWISS-PROT (3)   
Protein domain (4)   
   InterPro (4)   
All databases (48)   

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