KEGG   ENZYME: 1.14.14.50Help
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
BRITE hierarchy
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)
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
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
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

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