KEGG   ENZYME: 1.14.14.167
Entry
EC 1.14.14.167              Enzyme                                 

Name
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase;
CYP82X1 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
Reaction(IUBMB)
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH---hemoprotein reductase] + O2 = (13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11690]
Reaction(KEGG)
R11690
Substrate
(13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine;
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine;
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
This cytochrome P-450 (heme-thiolate) enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
History
EC 1.14.14.167 created 2018
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22096  (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
Genes
PSOM: 113322295
Reference
1  [PMID:25485687]
  Authors
Dang TT, Chen X, Facchini PJ
  Title
Acetylation serves as a protective group in noscapine biosynthesis in opium poppy.
  Journal
Nat Chem Biol 11:104-6 (2015)
DOI:10.1038/nchembio.1717
Reference
2  [PMID:27378283]
  Authors
Li Y, Smolke CD
  Title
Engineering biosynthesis of the anticancer alkaloid noscapine in yeast.
  Journal
Nat Commun 7:12137 (2016)
DOI:10.1038/ncomms12137
Reference
3  [PMID:29610307]
  Authors
Li Y, Li S, Thodey K, Trenchard I, Cravens A, Smolke CD
  Title
Complete biosynthesis of noscapine and halogenated alkaloids in yeast.
  Journal
Proc Natl Acad Sci U S A 115:E3922-E3931 (2018)
DOI:10.1073/pnas.1721469115
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.167
IUBMB Enzyme Nomenclature: 1.14.14.167
ExPASy - ENZYME nomenclature database: 1.14.14.167
BRENDA, the Enzyme Database: 1.14.14.167

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