KEGG   ENZYME: 1.14.19.68
Entry
EC 1.14.19.68               Enzyme                                 
Name
(S)-canadine synthase;
(S)-tetrahydroberberine synthase;
(S)-tetrahydrocolumbamine oxidase (methylenedioxy-bridge-forming);
CYP719A (gene name)
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)-tetrahydrocolumbamine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)
Reaction(IUBMB)
(S)-tetrahydrocolumbamine + [reduced NADPH---hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R04400]
Reaction(KEGG)
R04400
Substrate
(S)-tetrahydrocolumbamine [CPD:C04118];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(S)-canadine [CPD:C03329];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme catalyses an oxidative reaction that does not incorporate oxygen into the product. Oxidation of the methoxyphenol group of the alkaloid tetrahydrocolumbamine results in the formation of the methylenedioxy bridge of canadine.
History
EC 1.14.19.68 created 1999 as EC 1.1.3.36, transferred 2002 to EC 1.14.21.5, transferred 2018 to EC 1.14.19.68
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13395  (S)-stylopine/(S)-canadine/(S)-nandinine synthase
Genes
NNU104604446
PSOM113322097 113347890
Reference
1
  Authors
Rueffer, M. and Zenk, M.H.
  Title
Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis.
  Journal
Phytochemistry 36:1219-1223 (1994)
Reference
2  [PMID:12732624]
  Authors
Ikezawa N, Tanaka M, Nagayoshi M, Shinkyo R, Sakaki T, Inouye K, Sato F
  Title
Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells.
  Journal
J Biol Chem 278:38557-65 (2003)
DOI:10.1074/jbc.M302470200
  Sequence
Reference
3  [PMID:24316226]
  Authors
Dang TT, Facchini PJ
  Title
Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy.
  Journal
FEBS Lett 588:198-204 (2014)
DOI:10.1016/j.febslet.2013.11.037
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.68
IUBMB Enzyme Nomenclature: 1.14.19.68
ExPASy - ENZYME nomenclature database: 1.14.19.68
BRENDA, the Enzyme Database: 1.14.19.68
CAS: 114308-22-4

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