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(R,S)-6-O-methyllaudanosoline + O2
? + H2O2
-
-
-
-
?
(R,S)-crassifoline + O2
? + H2O2
-
-
-
-
?
(R,S)-laudanosoline + O2
? + H2O2
(S)-coreximine + O2
(13aS)-2,11-dihydroxy-3,10-dimethoxy-5,8,13,13a-tetrahydroisoquinolino[3,2-a]isoquinolin-7-ium + H2O2
-
-
-
-
?
(S)-laudanosine + H2O2
? + O2
-
-
-
-
?
(S)-N-methylcoclaurine + O2
(S)-coclaurine + H2O2
-
-
-
-
?
(S)-norsteponine + H2O2
? + O2
-
-
-
-
?
(S)-protosinomenine + O2
? + H2O2
(S)-reticuline + O2
(S)-scoulerine + H2O2
(S)-scoulerine + H2O2
(S)-reticuline + O2
-
-
-
-
r
(S)-tetrahydropalmatine + O2
palmatine + 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
-
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
-
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
-
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
-
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
-
-
-
?
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
-
-
-
-
?
cannabigerolic acid + O2
cannabidiolic acid + H2O2
-
-
-
?
cinnamyl alcohol + O2
cinnamyl aldehyde + H2O2
-
-
-
?
coniferyl alcohol + O2
coniferyl aldehyde + H2O2
-
-
-
?
reticuline + O2
(S)-scoulerine + (S)-coreximine + H2O2
-
50% conversion, ratio (S)-scoulerine to (S)-coreximine is >99 to <1
-
?
sinapyl alcohol + O2
sinapyl aldehyde + H2O2
-
-
-
?
additional information
?
-
(R,S)-laudanosoline + O2
? + H2O2
Berberis beaniana
-
specific for the (S)-enantiomer
-
-
?
(R,S)-laudanosoline + O2
? + H2O2
-
specific for the (S)-enantiomer
-
-
?
(S)-protosinomenine + O2
? + H2O2
Berberis beaniana
-
-
-
-
?
(S)-protosinomenine + O2
? + H2O2
-
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
Berberis beaniana
-
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
Berberis beaniana
-
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
-
-
393868, 393870, 393871, 657166, 660193, 674610, 687593, 690154, 700353, 744025, 746447 -
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
-
r
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
highest activity
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
first step of benzophenanthridine alkaloid biosynthesis
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
first step of isoquinoline and benzophenanthridine alkaloid biosynthesis, involved in sanguinarine pathway
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
the enzyme is involved in the biosynthetic pathway for benzophenanthridine alkaloids in California poppy, Eschscholzia californica, cells, related alkaloids, overview
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
(S)-scoulerine is further oxidized to dehydroscoulerine in a second oxidation step
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
first committed step in sanguinarine biosynthesis
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
first step of benzophenanthridine alkaloid biosynthesis
-
-
?
(S)-reticuline + O2
(S)-scoulerine + H2O2
-
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
-
-
?
additional information
?
-
enzyme employs an enantioselective oxidative C-C bond formation
-
-
?
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Bird, D.A.; Facchini, P.J.
Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant
Planta
213
888-897
2001
Papaver somniferum
brenda
Hauschild, K.; Pauli, H.H.; Kutchan, T.M.
Isolation and analysis of a gene bbe1 encoding the berberine bridge enzyme from the California poppy Eschscholzia californica
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1998
Eschscholzia californica
brenda
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Molecular characterization of berberine bridge enzyme genes from opium poppy
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1996
Papaver somniferum
brenda
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Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants
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270
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1995
Eschscholzia californica
brenda
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Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture
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35
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1994
Eschscholzia californica
brenda
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Stereochemistry of enzymatic formation of the berberine bridge in protoberine alkaloids
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110
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1988
Chelidonium majus
-
brenda
Steffens, P.; Nagakura, N.; Zenk, M.H.
Purification and characterization of the berberine bridge enzyme from Berberis beaniana cell cultures
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24
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1985
Berberis beaniana, Embryophyta
-
brenda
Steffens, P.; Nagakura, N.; Zenk, M.H.
The berberine bridge forming enzyme in tetrahydroprotoberberine synthesis
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25
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1984
Berberis beaniana
-
brenda
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The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum
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101
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Eschscholzia californica, Papaver somniferum
brenda
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Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids
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51
153-164
2003
Eschscholzia californica, Papaver somniferum
brenda
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Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment
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138
173-183
2005
Papaver somniferum (P93479), Papaver somniferum
brenda
Samanani, N.; Alcantara, J.; Bourgault, R.; Zulak, K.G.; Facchini, P.J.
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy
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47
547-563
2006
Papaver somniferum
brenda
Winkler, A.; Hartner, F.; Kutchan, T.M.; Glieder, A.; Macheroux, P.
Biochemical evidence that berberine bridge enzyme belongs to a novel family of flavoproteins containing a bi-covalently attached FAD cofactor
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281
21276-21285
2006
Eschscholzia californica
brenda
Samanani, N.; Park, S.; Facchini, P.J.
Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis
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17
915-926
2005
Thalictrum flavum subsp. glaucum
brenda
Winkler, A.; Kutchan, T.M.; Macheroux, P.
6-S-cysteinylation of bi-covalently attached FAD in berberine bridge enzyme tunes the redox potential for optimal activity
J. Biol. Chem.
282
24437-24443
2007
Eschscholzia californica
brenda
Fujii, N.; Inui, T.; Iwasa, K.; Morishige, T.; Sato, F.
Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells
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16
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2007
Eschscholzia californica
brenda
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Structural and mechanistic studies reveal the functional role of bicovalent flavinylation in berberine bridge enzyme
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284
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2009
Eschscholzia californica (P30986)
brenda
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4
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2008
Eschscholzia californica
brenda
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Berberine bridge enzyme catalyzes the six electron oxidation of (S)-reticuline to dehydroscoulerine
Phytochemistry
70
1092-1097
2009
Eschscholzia californica (P30986)
brenda
Gonzalez-Candelas, L.; Alamar, S.; Sanchez-Torres, P.; Zacarias, L.; Marcos, J.F.
A transcriptomic approach highlights induction of secondary metabolism in citrus fruit in response to Penicillium digitatum infection
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10
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2010
Citrus sinensis
brenda
Resch, V.; Schrittwieser, J.; Wallner, S.; MacHeroux, P.; Kroutil, W.
Biocatalytic oxidative C-C bond formation catalysed by the berberine bridge enzyme: Optimal reaction conditions
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353
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2011
Eschscholzia californica (P30986)
-
brenda
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Catalytic and structural role of a conserved active site histidine in berberine bridge enzyme
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51
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2012
Eschscholzia californica (P30986)
brenda
Gaweska, H.M.; Roberts, K.M.; Fitzpatrick, P.F.
Isotope effects suggest a stepwise mechanism for berberine bridge enzyme
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51
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2012
Eschscholzia californica
brenda
Resch, V.; Lechner, H.; Schrittwieser, J.H.; Wallner, S.; Gruber, K.; Macheroux, P.; Kroutil, W.
Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates
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18
13173-13179
2012
Eschscholzia californica (P30986)
brenda
Schrittwieser, J.H.; Resch, V.; Wallner, S.; Lienhart, W.D.; Sattler, J.H.; Resch, J.; Macheroux, P.; Kroutil, W.
Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids
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76
6703-6714
2011
Eschscholzia californica (P30986)
brenda
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Optimization of yeast-based production of medicinal protoberberine alkaloids
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14
144
2015
Papaver somniferum (P93479)
brenda
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Enantioselective oxidative aerobic dealkylation of N-ethyl benzylisoquinolines by employing the berberine bridge enzyme
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54
15051-15054
2015
Eschscholzia californica
brenda
Daniel, B.; Konrad, B.; Toplak, M.; Lahham, M.; Messenlehner, J.; Winkler, A.; Macheroux, P.
The family of berberine bridge enzyme-like enzymes A treasure-trove of oxidative reactions
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632
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2017
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Oxidation of monolignols by members of the berberine bridge enzyme family suggests a role in plant cell wall metabolism
J. Biol. Chem.
290
18770-18781
2015
Arabidopsis thaliana (O64743), Arabidopsis thaliana (Q93ZA3), Arabidopsis thaliana
brenda
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Transgenic and mutation-based suppression of a berberine bridge enzyme-like (BBL) gene family reduces alkaloid content in field-grown tobacco
PLoS ONE
10
e0117273
2015
Nicotiana tabacum
brenda
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Structure of a berberine bridge enzyme-like enzyme with an active site specific to the plant family Brassicaceae
PLoS ONE
11
e0156892
2016
Arabidopsis thaliana (Q9FI21), Arabidopsis thaliana
brenda
Hori, K.; Okano, S.; Sato, F.
Efficient microbial production of stylopine using a Pichia pastoris expression system
Sci. Rep.
6
22201
2016
Eschscholzia californica
brenda