Reaction: (1) 4'-O-methylnorbelladine + [reduced NADPH—hemoprotein reductase] + O2 = (4aR,10bS)-noroxomaritidine + [oxidized NADPH—hemoprotein reductase] + 2 H2O
(2) 4'-O-methylnorbelladine + [reduced NADPH—hemoprotein reductase] + O2 = (4aS,10bR)-noroxomaritidine + [oxidized NADPH—hemoprotein reductase] + 2 H2O
For diagram of reaction click here.
Glossary: 4'-O-methylnorbelladine = 5-({[2-(4-hydroxyphenyl)ethyl]amino}methyl)-2-methoxyphenol
noroxomaritidine = 8-hydroxy-9-methoxy-4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one
Other name(s): CYP96T1 (gene name)
Systematic name: 4'-O-methylnorbelladine,NADPH—hemoprotein reductase:oxygen oxidoreductase (noroxomaritidine-forming)
Comments: A P-450 (heme-thiolate) enzyme. The enzyme, characterized from Narcissus pseudonarcissus (daffodil), forms the two enantiomers of the Amaryllidacea alkaloid noroxomaritidine by catalysing intramolecular oxidative para-para' phenol coupling. The oxidation involves molecular oxygen without its incorporation into the product.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
References:
1. Kilgore, M.B., Augustin, M.M., May, G.D., Crow, J.A. and Kutchan, T.M. CYP96T1 of Narcissus sp. aff. pseudonarcissus catalyzes formation of the para-para' C-C phenol couple in the Amaryllidaceae alkaloids. Front. Plant Sci. 7 (2016) 225. [PMID: 26941773]