KEGG   ORTHOLOGY: K22365
Entry
K22365            Tight     KO                                     
Symbol
CYP71D1
Name
tabersonine 3-oxygenase [EC:1.14.14.50]
Pathway
map00901  Indole alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00965  Vinblastine biosynthesis, geissoschizine => vinblastine
Reaction
R11810  16-methoxytabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
R11811  tabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00901 Indole alkaloid biosynthesis
    K22365  CYP71D1; tabersonine 3-oxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K22365  CYP71D1; tabersonine 3-oxygenase
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
    1.14.14.50  tabersonine 3-oxygenase
     K22365  CYP71D1; tabersonine 3-oxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP71 family
   K22365  CYP71D1; tabersonine 3-oxygenase
Genes
AG: AKM12282(CYP71D1V2)
Reference
PMID:25918424
  Authors
Qu Y, Easson ML, Froese J, Simionescu R, Hudlicky T, De Luca V
  Title
Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.
  Journal
Proc Natl Acad Sci U S A 112:6224-9 (2015)
DOI:10.1073/pnas.1501821112
  Sequence
[ag:AKM12282]
LinkDB

KEGG   ENZYME: 1.14.14.50
Entry
EC 1.14.14.50               Enzyme                                 
Name
tabersonine 3-oxygenase;
T3O;
CYP71D1V2
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
16-methoxytabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
Reaction(IUBMB)
(1) 16-methoxytabersonine + [reduced NADPH---hemoprotein reductase] + O2 = (3R)-3-hydroxy-16-methoxy-1,2-didehydro-2,3-dihydrotabersonine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11810];
(2) tabersonine + [reduced NADPH---hemoprotein reductase] + O2 = (3R)-3-hydroxy-1,2-didehydro-2,3-dihydrotabersonine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11811]
Reaction(KEGG)
R11810 R11811
Substrate
16-methoxytabersonine [CPD:C11675];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
tabersonine [CPD:C09244]
Product
(3R)-3-hydroxy-16-methoxy-1,2-didehydro-2,3-dihydrotabersonine [CPD:C21678];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
(3R)-3-hydroxy-1,2-didehydro-2,3-dihydrotabersonine [CPD:C21683]
Comment
This cytochrome P-450 (heme thiolate) enzyme acts on 16-methoxytabersonine, leading to biosynthesis of vindoline in the plant Catharanthus roseus (Madagascar periwinkle). It can also act on tabersonine, resulting in the production of small amounts of vindorosine. The products are unstable and, in the absence of EC 1.1.99.41, 3-hydroxy-1,2-didehydro-2,3-dihydrotabersonine reductase, will convert into 3-epoxylated compounds.
History
EC 1.14.14.50 created 2017
Pathway
ec00901  Indole alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22365  tabersonine 3-oxygenase
Reference
1  [PMID:25918424]
  Authors
Qu Y, Easson ML, Froese J, Simionescu R, Hudlicky T, De Luca V
  Title
Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.
  Journal
Proc Natl Acad Sci U S A 112:6224-9 (2015)
DOI:10.1073/pnas.1501821112
  Sequence
[ag:AKM12282]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.50
IUBMB Enzyme Nomenclature: 1.14.14.50
ExPASy - ENZYME nomenclature database: 1.14.14.50
BRENDA, the Enzyme Database: 1.14.14.50
LinkDB

KEGG   REACTION: R11810
Entry
R11810                      Reaction                               
Name
16-methoxytabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
Definition
16-Methoxytabersonine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (3R)-3-Hydroxy-16-methoxy-1,2-didehydro-2,3-dihydrotabersonine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C11675 + C03024 + C00007 <=> C21678 + C03161 + C00001
Enzyme
1.14.14.50
Pathway
rn00901  Indole alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00965  Vinblastine biosynthesis, geissoschizine => vinblastine
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
    1.14.14.50
     R11810  16-Methoxytabersonine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (3R)-3-Hydroxy-16-methoxy-1,2-didehydro-2,3-dihydrotabersonine + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K22365  tabersonine 3-oxygenase [EC:1.14.14.50]
Other DBs
RHEA: 52483
LinkDB

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