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IUBMB Comments A cytochrome P -450 (heme-thiolate) protein found in plants. 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.
Synonyms
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(S)-N-methylcoclaurine oxidase (C-O phenol-coupling)
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(S)-N-methylcoclaurine oxidase [C-O phenol-coupling]
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benzyltetrahydroisoquinoline oxidase
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Cytochrome P450 80
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EC 1.1.3.34
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formerly
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EC 1.14.21.3
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formerly
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oxidase, benzyltetrahydroisoquinoline
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(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2 = berbamunine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2 = berbamunine + [oxidized NADPH-hemoprotein reductase] + 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
(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2 = berbamunine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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MetaCyc
bisbenzylisoquinoline alkaloid biosynthesis
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(S)-N-methylcoclaurine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (C-O phenol-coupling)
A cytochrome P-450 (heme-thiolate) protein found in plants. 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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(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + (S)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
(R,S)-berbamunine + (R,R)-guattegaumerine + (R,S)-2'-norberbamunine + [oxidized NADPH-hemoprotein reductase] + H2O
2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
berbamunine + guattegaumerine + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
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Substrates: 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 + [reduced NADPH-hemoprotein reductase] + O2
(R,S)-berbamunine + (R,R)-guattegaumerine + (R,S)-2'-norberbamunine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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(S)-N-methylcoclaurine + (R)-N-methylcoclaurine + (S)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
(R,S)-berbamunine + (R,R)-guattegaumerine + (R,S)-2'-norberbamunine + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: -
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
berbamunine + guattegaumerine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
berbamunine + guattegaumerine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
berbamunine + guattegaumerine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: enzyme mediates highly regiospecific and stereospecific oxidative phenol coupling to afford natural bisbenzylisoquinoline alkaloids
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2 (S)-N-methylcoclaurine + 2 (R)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
berbamunine + guattegaumerine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: enzyme mediates highly regiospecific and stereospecific oxidative phenol coupling to afford natural bisbenzylisoquinoline alkaloids
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cytochrome P450
enzyme contains 18.2 nmol of cytochrome P450 per mg of enzyme
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additional information
additional information
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additional information
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normal Michaelis-Menten kinetics are not observed for the formation of guattegaumerine or berbamunine
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additional information
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normal Michaelis-Menten kinetics are not observed for the formation of guattegaumerine or berbamunine
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additional information
additional information
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additional information
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additional information
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additional information
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7.5
formation of berbamunine or guattegaumerine
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35
formation of berbamunine
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formation of guattegaumerine
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18 - 46
50% of maximal activity at 18°C and 46°C, formation of guattegaumerine
22 - 46
50% of maximal activity at 22°C and 46°C
7 - 49
50% of maximal activity at 7°C and 49°C, formation of berbamunine
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SwissProt
brenda
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brenda
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brenda
Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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C80A1_BERST
487
1
55539
Swiss-Prot
Secretory Pathway (Reliability: 3 )
B9T2D0_RICCO
409
1
46189
TrEMBL
Secretory Pathway (Reliability: 2 )
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55474
x * 55474, calculation from nucleotide sequence
46000
x * 46000, SDS-PAGE
46000
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x * 46000, SDS-PAGE
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x * 46000, SDS-PAGE
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x * 55474, calculation from nucleotide sequence
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heterologously expressed enzyme from Sf9 cell culture
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expression in functional form in insect cell culture using a baculovirus-based expression system
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Stadler, R.; Zenk, M.H.
The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures
J. Biol. Chem.
268
823-831
1993
Berberis stolonifera (P47195)
brenda
Kraus, P.F.X.; Kutchan, T.M.
Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C-O phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera
Proc. Natl. Acad. Sci. USA
92
2071-2075
1995
Berberis stolonifera (P47195), Berberis stolonifera
brenda
Kutchan, T.M.
Heterologous expression of alkaloid biosynthetic genes - a review
Gene
179
73-81
1996
Berberis stolonifera (P47195), Berberis stolonifera
brenda
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