KEGG   ORTHOLOGY: K22094
Entry
K22094            Tight     KO                                     
Symbol
CYP82X2
Name
(S)-1-hydroxy-N-methylcanadine 13-hydroxylase [EC:1.14.14.163]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00946  Noscapine biosynthesis, (S)-reticuline => noscapine
Reaction
R11688  (S)-1-hydroxy-N-methylcanadine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (13-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22094  CYP82X2; (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K22094  CYP82X2; (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.163  (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
     K22094  CYP82X2; (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP82 family
   K22094  CYP82X2; (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
Genes
PSOM: 113322152
AG: AFB74616(CYP82X2)
Reference
PMID:22653730
  Authors
Winzer T, Gazda V, He Z, Kaminski F, Kern M, Larson TR, Li Y, Meade F, Teodor R, Vaistij FE, Walker C, Bowser TA, Graham IA
  Title
A Papaver somniferum 10-gene cluster for synthesis of the anticancer alkaloid noscapine.
  Journal
Science 336:1704-8 (2012)
DOI:10.1126/science.1220757
  Sequence
[ag:AFB74616]
Reference
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
LinkDB

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
LinkDB

KEGG   REACTION: R11688
Entry
R11688                      Reaction                               
Name
(S)-1-hydroxy-N-methylcanadine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (13-hydroxylating)
Definition
(S)-1-Hydroxy-cis-N-methylcanadine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (13S,14R)-1,13-Dihydroxy-cis-N-methylcanadine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C21586 + C03024 + C00007 <=> C21587 + C03161 + C00001
Reaction class
RC01552  C21586_C21587
Enzyme
1.14.14.163
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00946  Noscapine biosynthesis, (S)-reticuline => noscapine
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.163
     R11688  (S)-1-Hydroxy-cis-N-methylcanadine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (13S,14R)-1,13-Dihydroxy-cis-N-methylcanadine + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K22094  (S)-1-hydroxy-N-methylcanadine 13-hydroxylase [EC:1.14.14.163]
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
LinkDB

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