Oxidoreductases;
Catalysing the reaction X-H + Y-H = X-Y;
With oxygen as acceptor

(S)-reticuline:oxygen oxidoreductase (methylene-bridge-forming)

(S)-reticuline + O2 = (S)-scoulerine + H2O2 [RN:R03831]

R03831

(S)-reticuline [CPD:C02105];
O2 [CPD:C00007]

Contains FAD. The enzyme from the plant Eschscholtzia californica binds the cofactor covalently [3]. Acts on (S)-reticuline and related compounds, converting the N-methyl group into the methylene bridge ('berberine bridge') of (S)-tetrahydroprotoberberines. The product of the reaction, (S)-scoulerine, is a precursor of protopine, protoberberine and benzophenanthridine alkaloid biosynthesis in plants.

EC 1.21.3.3 created 1989 as EC 1.5.3.9, transferred 2002 to EC 1.21.3.3

1

Steffens, P., Nagakura, N. and Zenk, M.H.

The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis.

Tetrahedron Lett. 25 (1984) 951-952.

2  [PMID:1946465]

Dittrich H, Kutchan TM.

Molecular cloning, expression, and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack.

Proc. Natl. Acad. Sci. U. S. A. 88 (1991) 9969-73.

[ag:AAC39358]

3  [PMID:7592663]

Kutchan TM, Dittrich H.

Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants.

J. Biol. Chem. 270 (1995) 24475-81.