KEGG   ENZYME: 1.21.3.3Help
Entry
EC 1.21.3.3                 Enzyme                                 

Name
reticuline oxidase;
BBE;
berberine bridge enzyme;
berberine-bridge-forming enzyme;
tetrahydroprotoberberine synthase
Class
Oxidoreductases;
Catalysing the reaction X-H + Y-H = X-Y;
With oxygen as acceptor
BRITE hierarchy
Sysname
(S)-reticuline:oxygen oxidoreductase (methylene-bridge-forming)
Reaction(IUBMB)
(S)-reticuline + O2 = (S)-scoulerine + H2O2 [RN:R03831]
Reaction(KEGG)
Substrate
(S)-reticuline [CPD:C02105];
O2 [CPD:C00007]
Product
(S)-scoulerine [CPD:C02106];
H2O2 [CPD:C00027]
Comment
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.
History
EC 1.21.3.3 created 1989 as EC 1.5.3.9, transferred 2002 to EC 1.21.3.3
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K00307  reticuline oxidase
Reference
1
  Authors
Steffens, P., Nagakura, N. and Zenk, M.H.
  Title
The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis.
  Journal
Tetrahedron Lett 25:951-952 (1984)
Reference
2  [PMID:1946465]
  Authors
Dittrich H, Kutchan TM.
  Title
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.
  Journal
Proc Natl Acad Sci U S A 88:9969-73 (1991)
DOI:10.1073/pnas.88.22.9969
  Sequence
Reference
3  [PMID:7592663]
  Authors
Kutchan TM, Dittrich H.
  Title
Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants.
  Journal
J Biol Chem 270:24475-81 (1995)
DOI:10.1074/jbc.270.41.24475
Other DBs
ExplorEnz - The Enzyme Database: 1.21.3.3
IUBMB Enzyme Nomenclature: 1.21.3.3
ExPASy - ENZYME nomenclature database: 1.21.3.3
BRENDA, the Enzyme Database: 1.21.3.3
CAS: 152232-28-5

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