Information on EC 1.14.21.3 - berbamunine synthase

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The expected taxonomic range for this enzyme is: Berberis stolonifera

EC NUMBER
COMMENTARY hide
1.14.21.3
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RECOMMENDED NAME
GeneOntology No.
berbamunine synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + NADPH + H+ + O2 = berbamunine + NADP+ + 2 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
bisbenzylisoquinoline alkaloid biosynthesis
-
-
Isoquinoline alkaloid biosynthesis
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
144941-42-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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+
show the reaction diagram
2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + 2 NADPH + 2 H+ + 2 O2
berbamunine + guattegaumerine + 2 NADP+ + 4 H2O
show the reaction diagram
additional information
?
-
-
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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-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
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
show the reaction diagram
-
enzyme mediates highly regiospecific and stereospecific oxidative phenol coupling to afford natural bisbenzylisoquinoline alkaloids
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-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
enzyme contains 18.2 nmol of cytochrome P450 per mg of enzyme
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
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 hide
LITERATURE
IMAGE
additional information
additional information
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
formation of berbamunine or guattegaumerine
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
-
formation of berbamunine
38
-
formation of guattegaumerine
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 49
-
50% of maximal activity at 7C and 49C, formation of berbamunine
18 - 46
-
50% of maximal activity at 18C and 46C, formation of guattegaumerine
22 - 46
-
50% of maximal activity at 22C and 46C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
46000
-
x * 46000, SDS-PAGE
55474
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x * 55474, calculation from nucleotide sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
heterologously expressed enzyme from Sf9 cell culture
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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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