KEGG   ENZYME: 1.14.19.73
Entry
EC 1.14.19.73               Enzyme                                 
Name
(S)-nandinine synthase;
CYP719A3
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)-nandinine-forming]
Reaction(IUBMB)
(S)-scoulerine + [reduced NADPH---hemoprotein reductase] + O2 = (S)-nandinine + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R11405]
Reaction(KEGG)
R11405
Substrate
(S)-scoulerine [CPD:C02106];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(S)-nandinine [CPD:C21370];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) enzyme found in plants. The enzyme catalyses an oxidative reaction that does not incorporate oxygen into the product. Forms the methylenedioxy bridge of the protoberberine alkaloid (S)-nandinine by the oxidative ring closure of adjacent phenolic and methoxy groups of (S)-scoulerine. cf. EC 1.14.19.65, (S)-cheilanthifoline synthase, which catalyses a similar reaction at the other side of the (S)-scoulerine molecule, forming (S)-cheilanthifoline.
History
EC 1.14.19.73 created 2016 as EC 1.14.21.12, transferred 2018 to EC 1.14.19.73
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  [PMID:17250743]
  Authors
Ikezawa N, Iwasa K, Sato F
  Title
Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica.
  Journal
FEBS J 274:1019-35 (2007)
DOI:10.1111/j.1742-4658.2007.05652.x
  Sequence
[ag:BAD98249]
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:ABR14721]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.73
IUBMB Enzyme Nomenclature: 1.14.19.73
ExPASy - ENZYME nomenclature database: 1.14.19.73
BRENDA, the Enzyme Database: 1.14.19.73

  All links  
Pathway (2)   
   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 (4)   
   UniProt (2)   
   SWISS-PROT (2)   
Protein domain (4)   
   InterPro (4)   
All databases (40)   

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