Reaction: (1) 16-methoxytabersonine + [reduced NADPH hemoprotein reductase] + O2 = (3R)-3-hydroxy-16-methoxy-1,2-didehydro-2,3-dihydrotabersonine + [oxidized NADPH hemoprotein reductase] + H2O
(2) tabersonine + [reduced NADPH hemoprotein reductase] + O2 = (3R)-3-hydroxy-1,2-didehydro-2,3-dihydrotabersonine + [oxidized NADPH hemoprotein reductase] + H2O
For diagram of reaction, click here
Other name(s): T3O; CYP71D1V2
Systematic name: 16-methoxytabersonine,[reduced NADPH hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
Comments: 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 188.8.131.52, 3-hydroxy-1,2-didehydro-2,3-dihydrotabersonine reductase, will convert into 3-epoxylated compounds.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
1. Qu, Y., Easson, M.L., Froese, J., Simionescu, R., Hudlicky, T. and De Luca, V. Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. Proc. Natl Acad. Sci. USA 112 (2015) 6224-6229. [PMID: 25918424]