The Enzyme Database

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Accepted name: methyltetrahydroprotoberberine 14-monooxygenase
Reaction: (1) (S)-cis-N-methylcanadine + [reduced NADPH—hemoprotein reductase] + O2 = allocryptopine + [oxidized NADPH—hemoprotein reductase] + H2O
(2) (S)-cis-N-methylstylopine + [reduced NADPH—hemoprotein reductase] + O2 = protopine + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of canadine biosynthesis, click here and for diagram of stylopine biosynthesis, click here
Other name(s): methyltetrahydroprotoberberine 14-hydroxylase; (S)-cis-N-methyltetrahydroberberine 14-monooxygenase; (S)-cis-N-methyltetrahydroprotoberberine-14-hydroxylase; CYP82N4 (gene name); (S)-N-methylcanadine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating); (S)-cis-N-methylstylopine 14-hydroxylase
Systematic name: (S)-cis-N-methylcanadine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating)
Comments: A cytochrome P-450 (heme-thiolate) protein involved in the biosynthesis of isoquinoline alkaloids in plants. It also hydroxylates (S)-cis-N-methyltetrahydrothalifendine, and (S)-cis-N-methyltetrahydropalmatine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 113478-42-5
1.  Rueffer, M. and Zenk, M.H. Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans. Tetrahedron Lett. 28 (1987) 5307–5310. [DOI]
2.  Beaudoin, G.A. and Facchini, P.J. Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis. Biochem. Biophys. Res. Commun. 431 (2013) 597–603. [DOI] [PMID: 23313486]
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