Berbamunine synthase

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In enzymology, berbamunine synthase (EC 1.14.19.66, Formerly EC 1.1.3.34 and EC 1.14.21.3) is an enzyme that catalyzes the combination of two benzylisoquinoline alkaloids

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O2
2 H2O
Berbamunine synthase
 
 
 

The enzyme has a cofactor, a reduced nicotinamide adenine dinucleotide phosphate in combination with a hemoprotein, which allows it to use molecular oxygen to oxidatively combine the alkaloid substrates. [1] [2] [3]

It can combine related alkaloids differing only in the degree of methylation of the phenolic oxygens. For example, (S)-coclaurine also reacts with (R)-N-methylcoclaurine to give 2'-norberbamunine and dimerisation of (R)-N-methylcoclaurine gives guattegaumerine. [1] [3]

+
 
 
O2
2 H2O
Berbamunine synthase
 
 
 
berbamunine synthase
Identifiers
EC no. 1.14.19.66
CAS no. 144941-42-4
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum
Gene Ontology AmiGO / QuickGO
Search
PMC articles
PubMed articles
NCBI proteins

The enzyme belongs to the family of oxidoreductases and its systematic name is (S)-N-methylcoclaurine,NADPH:oxygen oxidoreductase (C-O phenol-coupling). It is also called (S)-N-methylcoclaurine oxidase (C-O phenol-coupling). It was first isolated from Berberis stolonifera and participates in alkaloid biosynthesis. [2] [3]

References

  1. 1 2 Enzyme 1.14.19.66) at KEGG Pathway Database.
  2. 1 2 Stadler R, Zenk MH (1993). "The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures". J. Biol. Chem. 268 (2): 823–31. doi: 10.1016/S0021-9258(18)54008-4 . PMID   8380416.
  3. 1 2 3 Tian Y, Kong L, Li Q, Wang Y, Wang Y, An Z, Ma Y, Tian L, Duan B, Sun W, Gao R, Chen S, Xu Z (November 2024). "Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids". Natural Product Reports. 41 (11): 1787–1810. doi:10.1039/d4np00029c. PMID   39360417.