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Information on EC 1.14.19.68 - (S)-canadine synthase
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1.14.19.68 (S)-canadine synthaseIUBMB Comments
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme catalyses an oxidative reaction that does not incorporate oxygen into the product. Oxidation of the methoxyphenol group of the alkaloid tetrahydrocolumbamine results in the formation of the methylenedioxy bridge of canadine.
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
cas-1, cyp719a13, cyp719a21, (s)-canadine synthase, canadine synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-tetrahydroberberine synthase
-
-
-
-
(S)-tetrahydrocolumbamine oxidase (methylenedioxy-bridge-forming)
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-
-
-
canadine synthase
EC 1.1.3.36
-
-
formerly
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EC 1.14.21.5
-
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formerly
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canadine synthase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
formation of a methylenedioxy bridge in ring A
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(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
-
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redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(S)-tetrahydrocolumbamine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme catalyses an oxidative reaction that does not incorporate oxygen into the product. Oxidation of the methoxyphenol group of the alkaloid tetrahydrocolumbamine results in the formation of the methylenedioxy bridge of canadine.
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CAS REGISTRY NUMBER
COMMENTARY
114308-22-4
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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)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
reaction in protoberberine biosynthetic pathway
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
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strict substrate specificity and high affinity for (S)-tetrahydrocolumbamine
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
reaction in protoberberine biosynthetic pathway
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
high substrate specificity
(S)-canadine is identical with (S)-tetrahydroberberine
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
penultimate step in the biosynthesis of the protoberberine alkaloid, berberine
(S)-canadine is identical with (S)-tetrahydroberberine
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
?
-
23% of the activity compared to NADPH
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
?
-
23% of the activity compared to NADPH
-
-
?
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NATURAL SUBSTRATE
NATURAL 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)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
reaction in protoberberine biosynthetic pathway
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
strict substrate specificity and high affinity for (S)-tetrahydrocolumbamine
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
reaction in protoberberine biosynthetic pathway
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-canadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
penultimate step in the biosynthesis of the protoberberine alkaloid, berberine
(S)-canadine is identical with (S)-tetrahydroberberine
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
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the enzyme forms a complex with a cytochrome P-450 reductase
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Diabetes Mellitus, Type 2
Caspase activation in retinas of diabetic and galactosemic mice and diabetic patients.
Endotoxemia
Role of caspase 1 in murine antibacterial host defenses and lethal endotoxemia.
Escherichia coli Infections
Role of caspase 1 in murine antibacterial host defenses and lethal endotoxemia.
Galactosemias
Caspase activation in retinas of diabetic and galactosemic mice and diabetic patients.
Glioblastoma
Chemosensitivity of glioblastoma cells during treatment with the organo-tin compound triethyltin(IV)lupinylsulfide hydrochloride.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.033
[reduced NADPH-hemoprotein reductase]
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canadine synthase in complex with a cytochrome P-450 reductase
0.0115
(S)-tetrahydrocolumbamine
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canadine synthase in complex with a cytochrome P-450 reductase
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Thalictrum flavum ssp. glaucum
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immature endodermis and surrounding tissues, in situ hybridization
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
virus-induced gene silencing of CYP719A21 causes a significant increase in (S)-tetrahydrocolumbamine accumulation and a corresponding decrease in the levels of putative downstream intermediates and noscapine
metabolism
the enzyme is involved in berberine biosynthesis in Coptis chinensis
physiological function
CYP719A13 can be involved in both sanguinarine and berberine formation in Argemone mexicana
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). C719D_ARGME
504
1
57452
Swiss-Prot
other Location (Reliability: 4)
C7A21_PAPSO
488
1
55176
Swiss-Prot
Secretory Pathway (Reliability: 1)
C7193_ESCCA
495
1
56806
Swiss-Prot
Secretory Pathway (Reliability: 2)
C719A_COPJA
491
1
55353
Swiss-Prot
Secretory Pathway (Reliability: 2)
R4QPW0_9MAGN
491
1
55287
TrEMBL
Secretory Pathway (Reliability: 2)
Q5C9L1_THLFG
492
1
55376
TrEMBL
Secretory Pathway (Reliability: 1)
R4QPW0_9MAGN
491
1
55287
TrEMBL
other Location (Reliability: 1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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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
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
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
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Galneder, E.; Rueffer, M.; Wanner, G.; Tabata, M.; Zenk, M.H.
Alternative final steps in berberine biosynthesis in Coptis japonica cell cultures
Plant Cell Rep.
7
1-4
1988
Coptis japonica
brenda
Rueffer, M.; Zenk, M.H.
Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis
Phytochemistry
36
1219-1223
1994
Berberis aristata, Berberis crataegina, Berberis henryana, Berberis stolonifera, Berberis taliensis, Coptis japonica, Thalictrum glabrum, Thalictrum glaucum, Thalictrum macrocarpum, Thalictrum tuberosum
-
brenda
Rueffer, M.
New reactions in the protoberberine biosynthetic pathway
Chem. Listy
87
215-217
1993
Berberidaceae, Ranunculaceae
-
brenda
Samanani, N.; Park, S.; Facchini, P.J.
Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis
Plant Cell
17
915-926
2005
Thalictrum flavum ssp. glaucum
brenda
Diaz Chavez, M.L.; Rolf, M.; Gesell, A.; Kutchan, T.M.
Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana
Arch. Biochem. Biophys.
507
186-193
2011
Argemone mexicana (B1NF19), Argemone mexicana
brenda
Dang, T.T.; Facchini, P.J.
Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy
FEBS Lett.
588
198-204
2014
Papaver somniferum
brenda
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Thalictrum flavum subsp. glaucum (Q5C9L1)
brenda
He, Y.; Hou, P.; Fan, G.; Li, D.; Peng, C.
Isolation and characterization of a novel (S)-canadine synthase gene from Coptis chinensis
Electron. J. Biotechnol.
18
376-380
2015
Coptis chinensis (R4QPW0)
-
brenda
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