1.21.3.3: reticuline oxidase
This is an abbreviated version!
For detailed information about reticuline oxidase, go to the full flat file.
Word Map on EC 1.21.3.3
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1.21.3.3
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poppy
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sanguinarine
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s-reticuline
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s-scoulerine
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papaver
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benzylisoquinoline
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somniferum
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opium
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benzophenanthridine
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codeinone
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cyp80b1
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eschscholtzia
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papaveraceae
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vanillyl
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flavinylated
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3\'-hydroxylase
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s-norcoclaurine
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synthesis
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medicine
- 1.21.3.3
- poppy
- sanguinarine
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s-reticuline
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s-scoulerine
- papaver
-
benzylisoquinoline
- somniferum
-
opium
-
benzophenanthridine
- codeinone
- cyp80b1
-
eschscholtzia
- papaveraceae
-
vanillyl
-
flavinylated
-
3\'-hydroxylase
-
s-norcoclaurine
- synthesis
- medicine
Reaction
Synonyms
(S)-reticuline oxidase, BBE, BBE-like 13, BBE-like 15, BBE-like 28, BBE1, BBL, berberine bridge enzyme, berberine bridge enzyme-like, berberine bridge enzyme-like 28, berberine bridge-forming enzyme, berberine-bridge-forming enzyme, EC 1.5.3.9, flavin-dependent oxidase, monolignol oxidoreductase, reticuline oxidase, tetrahydroprotoberberine synthase
ECTree
1.21.3.3 reticuline oxidaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.21.3.3 - reticuline oxidase
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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)-coreximine + O2
(13aS)-2,11-dihydroxy-3,10-dimethoxy-5,8,13,13a-tetrahydroisoquinolino[3,2-a]isoquinolin-7-ium + H2O2
-
-
-
-
?
1-(2-fluoro-3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol + O2
(13aS)-12-fluoro-3-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,11-diol + H2O
-
49% conversion, more than 99% of product (13aS)-12-fluoro-3-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,11-diol
-
?
1-(2-fluoro-3-hydroxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol + O2
(13aS)-12-fluoro-2-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,11-diol + H2O
-
49% conversion, more than 99% of product (13aS)-12-fluoro-2-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,11-diol
-
?
1-(3-hydroxy-4-methoxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol + O2
(13aS)-2,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,9-diol + isocoreximine + H2O2
-
53% conversion, ratio (13aS)-2,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,9-diol to isocoreximine is 98:2
-
?
1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol + O2
(13aS)-3-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol + (1R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol + H2O2
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reaction leads to the (S)-enantiomer of the product and enantiomerically pure (R)-substrate. 22% yield of (13aS)-3-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol in more than 97% enantiomeric excess, 549% yield of + (1R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-olin more than 97% enantiomeric excess
-
?
1-[(4-chlorophenyl)methyl]-2-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline + O2
(1S)-1-[(4-chlorophenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline + (1R)-1-[(4-chlorophenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline + H2O2
-
-
-
-
?
2-ethyl-6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline + O2
(1S)-6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline + (1R)-6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline + H2O2
-
-
-
-
?
2-ethyl-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline + O2
(1S)-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline + (1R)-2-ethyl-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline + H2O2
-
-
-
-
?
3-[(2-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol + O2
3-[[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol + 3-[[(1R)-2-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol + H2O2
-
-
-
-
?
3-[(2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol + O2
(13aS)-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-9-ol + 3-[[(1R)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol + H2O2
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reaction leads to the (S)-enantiomer of the product and enantiomerically pure (R)-substrate. 46% yield of (13aS)-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-9-ol in more than 97% enantiomeric excess, 49% yield of + 3-[[(1R)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol in more than 97% enantiomeric excess
-
?
3-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-fluorophenol + O2
(13aS)-12-fluoro-2,3-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-11-ol + H2O
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48% conversion, more than 99% of product (13aS)-12-fluoro-2,3-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-11-ol
-
?
3-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol + O2
(13aS)-2,3-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-9-ol + 3-[[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol + H2O2
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reaction leads to the (S)-enantiomer of the product and enantiomerically pure (R)-substrate. 42% yield of (13aS)-2,3-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-9-ol in more than 97% enantiomeric excess, 50% yield of + 3-[[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenol in more than 97% enantiomeric excess
-
?
4-coumaryl alcohol + O2
4-coumaryl aldehyde + H2O2
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-
-
?
6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline + H2O2
? + O2
-
-
-
-
?
6-ethyl-5-[(4-methoxyphenyl)methyl]-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinoline + O2
(5S)-5-[(4-methoxyphenyl)methyl]-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinoline + (5R)-5-[(4-methoxyphenyl)methyl]-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinoline + H2O2
-
-
-
-
?
reticuline + O2
(S)-scoulerine + (S)-coreximine + H2O2
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50% conversion, ratio (S)-scoulerine to (S)-coreximine is >99 to <1
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?
(R,S)-laudanosoline + O2
? + H2O2
Berberis beaniana
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specific for the (S)-enantiomer
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-
?
(R,S)-laudanosoline + O2
? + H2O2
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specific for the (S)-enantiomer
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
Berberis beaniana
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reticuline is the biogenic precursor of the protoberine skeleton
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
highest activity
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-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
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first step of benzophenanthridine alkaloid biosynthesis
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-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
first step of isoquinoline and benzophenanthridine alkaloid biosynthesis, involved in sanguinarine pathway
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
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the enzyme is involved in the biosynthetic pathway for benzophenanthridine alkaloids in California poppy, Eschscholzia californica, cells, related alkaloids, overview
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-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
(S)-scoulerine is further oxidized to dehydroscoulerine in a second oxidation step
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
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first committed step in sanguinarine biosynthesis
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
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first step of benzophenanthridine alkaloid biosynthesis
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
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first step of isoquinoline and benzophenanthridine alkaloid biosynthesis, involved in sanguinarine pathway
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
first step of isoquinoline and benzophenanthridine alkaloid biosynthesis, involved in sanguinarine pathway
-
-
?
additional information
?
-
-
C-H bond cleavage is rate-limiting during flavin reduction. Solvent isotope effects on kred indicate that solvent exchangeable protons are not in flight during or before flavin reduction, thus eliminating a fully concerted mechanism. Deprotonation is not occurring before or during C-H bond cleavage, and a hydroxyl group must be present at C3 for cyclization. This could be due to the methoxy group being less electron-donating than a hydroxyl substituent or to disruption of the interaction between the glutamate and the substrate, causing altered binding. A concerted attack of a methyl amine by the C2-atom and hydride transfer is less likely than attack on a methylene iminium ion intermediate by the C2-atom, indicating that a stepwise mechanism is the likely mechanism
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-
?
additional information
?
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enzyme employs an enantioselective oxidative C-C bond formation
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?
