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
NNU104604446
PSOM113322097 113347890
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
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
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

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