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Information on EC 1.21.3.3 - reticuline oxidase and Organism(s) Papaver somniferum and UniProt Accession P93479

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EC Tree
     1 Oxidoreductases
         1.21 Catalysing the reaction X-H + Y-H = X-Y
             1.21.3 With oxygen as acceptor
                1.21.3.3 reticuline oxidase
IUBMB Comments
Contains FAD. The enzyme from the plant Eschscholtzia californica binds the cofactor covalently . Acts on (S)-reticuline and related compounds, converting the N-methyl group into the methylene bridge ('berberine bridge') of (S)-tetrahydroprotoberberines. The product of the reaction, (S)-scoulerine, is a precursor of protopine, protoberberine and benzophenanthridine alkaloid biosynthesis in plants.
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Papaver somniferum
UNIPROT: P93479
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The taxonomic range for the selected organisms is: Papaver somniferum
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
berberine bridge enzyme, berberine bridge enzyme-like, flavin-dependent oxidase, reticuline oxidase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
berberine bridge enzyme
-
flavin-dependent oxidase
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reticuline oxidase
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BBE
-
-
-
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berberine bridge enzyme
-
-
-
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berberine-bridge-forming enzyme
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-
-
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tetrahydroprotoberberine synthase
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
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oxidation
-
-
-
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reduction
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
(S)-reticuline:oxygen oxidoreductase (methylene-bridge-forming)
Contains FAD. The enzyme from the plant Eschscholtzia californica binds the cofactor covalently [3]. Acts on (S)-reticuline and related compounds, converting the N-methyl group into the methylene bridge ('berberine bridge') of (S)-tetrahydroprotoberberines. The product of the reaction, (S)-scoulerine, is a precursor of protopine, protoberberine and benzophenanthridine alkaloid biosynthesis in plants.
CAS REGISTRY NUMBER
COMMENTARY hide
152232-28-5
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-reticuline + O2
(S)-scoulerine + H2O2
show the reaction diagram
(S)-reticuline + O2
(S)-scoulerine + H2O2
show the reaction diagram
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-reticuline + O2
(S)-scoulerine + H2O2
show the reaction diagram
(S)-reticuline + O2
(S)-scoulerine + H2O2
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9 - 10
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completely inactive at acidic or neutral pH
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
of seedling, localization in the sieve elelments
Manually annotated by BRENDA team
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sieve elements of root and hypocotyl, abundance of enzyme increases rapidly between 1 and 3 days of germination
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
associated to endoplasmic reticulum
Manually annotated by BRENDA team
-
vacuolar pH is below the functional range of BBE, it is active only before the entry into the vacuole, enters vacuole via a sorting determinant
Manually annotated by BRENDA team
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smooth vesicle with basic pH
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
RETO_PAPSO
535
0
59903
Swiss-Prot
Secretory Pathway (Reliability: 2)
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
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undergoes N-glycosylation
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
recombinant coexpression of seven enzymes, including the three membrane-bound enzymes: the flavin-dependent oxidase berberine bridge enzyme, the cytochrome P450 canadine synthase, and a cytochrome P450 reductase, in Saccharomyces cerevisiae results in protoberberine alkaloid production from a simple benzylisoquinoline alkaloid precursor rac-norlaudanosoline. Improvement of flux through the pathway, by methods including enzyme variant screening, genetic copy number variation, and culture optimization, leading to an over 70fold increase in canadine titer up to 1.8 mg/l
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
canadine-producing Saccharomyces cerevisiae strain harbors expression cassettes for seven heterologous enzymes: Papaper somniferum norcoclaurine 6-O-methyltransferase (Ps6OMT), Papaver somniferum 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase 2 (Ps4'OMT), Papapver somniferum coclaurine N-methyltransferase (PsCNMT), Papaver somniferum berberine bridge enzyme (PsBBE), Thalictrum flavum scoulerine 9-O-methyltransferase (TfS9OMT), Thalictrum flavum canadine synthase (TfCAS), and Arabidopsis thaliana cytochrome P450 reductase 1 (CPR). The expression cassettes for the methyltransferases Ps6OMT, PsCNMT, and Ps4'OMT and the cytochrome P450 reductase CPR were chromosomally integrated, TfS9OMT and TfCAS are expressed from a high-copy plasmid, and PsBBE is expressed from a second high-copy plasmid
expressed in Escherichia coli BL21
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sense and antisense constructs expressed in root tissue
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
a Saccharomyces cerevisiae strain is engineered to express seven heterologous enzymes (Papaper somniferum norcoclaurine 6-O-methyltransferase (Ps6OMT), Papaver somniferum 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase 2 (Ps4'OMT), Papapver somniferum coclaurine N-methyltransferase (PsCNMT), Papaver somniferum berberine bridge enzyme (PsBBE), Thalictrum flavum scoulerine 9-O-methyltransferase (TfS9OMT), Thalictrum flavum canadine synthase (TfCAS), and Arabidopsis thaliana cytochrome P450 reductase 1 (CPR)), resulting in protoberberine alkaloid production from a simple benzylisoquinoline alkaloid precursor. A number of strategies are implemented to improve flux through the pathway, including enzyme variant screening, genetic copy number variation, and culture optimization. This leads to an over 70-fold increase in canadine titer up to 1.8 mg/l. Increased canadine titers enable extension of the pathway to produce berberine, a major constituent of several traditional medicines in a microbial host. This strain is viable at pilot scale
synthesis
heterologous production of berberine and the optimization of the engineered biosynthetic pathway from rac-norlaudanosoline to (S)-canadine in yeast involving the recombinant berberine reductase
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Manually annotated by BRENDA team
Facchini, P.J.; Penzes, C.; Johnson, A.G.; Bull, D.
Molecular characterization of berberine bridge enzyme genes from opium poppy
Plant Physiol.
112
1669-1677
1996
Papaver somniferum
Manually annotated by BRENDA team
Weid, M.; Ziegler, J.; Kutchan, T.M.
The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum
Proc. Natl. Acad. Sci. USA
101
13957-13962
2004
Eschscholzia californica, Papaver somniferum
Manually annotated by BRENDA team
Park, S.U.; Yu, M.; Facchini, P.J.
Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids
Plant Mol. Biol.
51
153-164
2003
Eschscholzia californica, Papaver somniferum
Manually annotated by BRENDA team
Alcantara, J.; Bird, D.A.; Franceschi, V.R.; Facchini, P.J.
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment
Plant Physiol.
138
173-183
2005
Papaver somniferum (P93479), Papaver somniferum
Manually annotated by BRENDA team
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
Plant J.
47
547-563
2006
Papaver somniferum
Manually annotated by BRENDA team
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Papaver somniferum (P93479)
Manually annotated by BRENDA team