KEGG   ENZYME: 1.14.14.163
Entry
EC 1.14.14.163              Enzyme                                 
Name
(S)-1-hydroxy-N-methylcanadine 13-hydroxylase;
CYP82X2 (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
(S)-1-hydroxy-cis-N-methylcanadine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (13-hydroxylating)
Reaction(IUBMB)
(S)-1-hydroxy-cis-N-methylcanadine + [reduced NADPH---hemoprotein reductase] + O2 = (13S,14R)-1,13-dihydroxy-cis-N-methylcanadine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11688]
Reaction(KEGG)
R11688
Substrate
(S)-1-hydroxy-cis-N-methylcanadine [CPD:C21586];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(13S,14R)-1,13-dihydroxy-cis-N-methylcanadine [CPD:C21587];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
The enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
History
EC 1.14.14.163 created 2018
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22094  (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
Genes
PSOM: 113322152
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
  Sequence
[ag:AFB74616]
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
  Sequence
[ag:AFB74616]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.163
IUBMB Enzyme Nomenclature: 1.14.14.163
ExPASy - ENZYME nomenclature database: 1.14.14.163
BRENDA, the Enzyme Database: 1.14.14.163

  All links  
Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical substance (6)   
   KEGG COMPOUND (6)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
Gene (3)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (2)   
Protein sequence (2)   
   UniProt (1)   
   SWISS-PROT (1)   
Protein domain (5)   
   InterPro (5)   
All databases (25)   

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