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Enzyme Nomenclature
Information on EC 1.14.21.3 - berbamunine synthase
Word Map on EC 1.14.21.3
- 1.14.21.3
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alkaloid
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bisbenzylisoquinoline
- poppy
- frugiperda
- stolonifera
- berberis
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nadph-cytochrome
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p450-dependent
- californica
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opium
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clans
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spodoptera
- papaver
- somniferum
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The expected taxonomic range for this enzyme is: Berberis stolonifera
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EC NUMBER 
COMMENTARY 
1.14.21.3
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RECOMMENDED NAME
GeneOntology No.
berbamunine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + NADPH + H+ + O2 = berbamunine + NADP+ + 2 H2O
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + NADPH + H+ + O2 = berbamunine + NADP+ + 2 H2O
regioselective and stereoselective formation of a C-O phenol couple in bisbenzylisoquinoline alkaloid biosynthesis without concomitant incorporation of activated oxygen into the product
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(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + NADPH + H+ + O2 = berbamunine + NADP+ + 2 H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(S)-N-methylcoclaurine,NADPH:oxygen oxidoreductase (C-O phenol-coupling)
A heme-thiolate enzyme (P-450). Forms the bisbenzylisoquinoline alkaloid berbamunine by phenol oxidation of N-methylcoclaurine without the incorporation of oxygen into the product. Reaction of two molecules of (R)-N-methylcoclaurine gives the dimer guattagaumerine.
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CAS REGISTRY NUMBER
COMMENTARY
144941-42-4
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + (S)-coclaurine + NADPH + O2
(R,S)-berbamunine + (R,R)-guattegaumerine + (R,S)-2'-norberbamunine + NADP+
2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + 2 NADPH + 2 H+ + 2 O2
berbamunine + guattegaumerine + 2 NADP+ + 4 H2O
additional information
?
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incubation with (S)-N-methylcoclaurine and (R)-coclaurine does not lead to a dimeric product, as well as incubations with (S)-N-methylcoclaurine alone or with either (S)-coclaurine or (R)-coclaurine together or individually
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(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + (S)-coclaurine + NADPH + O2
(R,S)-berbamunine + (R,R)-guattegaumerine + (R,S)-2'-norberbamunine + NADP+
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(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + (S)-coclaurine + NADPH + O2
(R,S)-berbamunine + (R,R)-guattegaumerine + (R,S)-2'-norberbamunine + NADP+
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + 2 NADPH + 2 H+ + 2 O2
berbamunine + guattegaumerine + 2 NADP+ + 4 H2O
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incubation with equimolar amounts of both (R)-N-methylcoclaurine and (S)-N-methylcoclaurine leads to the formation of berbamunine and guattegaumerine
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + 2 NADPH + 2 H+ + 2 O2
berbamunine + guattegaumerine + 2 NADP+ + 4 H2O
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two molecules of (R)-N-methylcoclaurine for the (R,R) dimer guattegaumerine or one molecule each of (R)-N-methylcoclaurine and (S)-N-methylcoclaurine form the (R,S) dimer berbamunine. The ratio of the two bisbenzylisoquinolines formed can be altered by the reductase source or by varying the enantiomer composition of the substrates
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + 2 NADPH + 2 H+ + 2 O2
berbamunine + guattegaumerine + 2 NADP+ + 4 H2O
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enzyme mediates highly regiospecific and stereospecific oxidative phenol coupling to afford natural bisbenzylisoquinoline alkaloids
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + 2 NADPH + 2 H+ + 2 O2
berbamunine + guattegaumerine + 2 NADP+ + 4 H2O
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enzyme mediates highly regiospecific and stereospecific oxidative phenol coupling to afford natural bisbenzylisoquinoline alkaloids
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
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enzyme contains 18.2 nmol of cytochrome P450 per mg of enzyme
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
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normal Michaelis-Menten kinetics are not observed for the formation of guattegaumerine or berbamunine
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7 - 49
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50% of maximal activity at 7°C and 49°C, formation of berbamunine
18 - 46
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50% of maximal activity at 18°C and 46°C, formation of guattegaumerine
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
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x * 46000, SDS-PAGE; x * 55474, calculation from nucleotide sequence
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in functional form in insect cell culture using a baculovirus-based expression system; expression in Sf9 cells
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.21.3)
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