Information on EC 1.14.21.1 - (S)-stylopine synthase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.21.1
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RECOMMENDED NAME
GeneOntology No.
(S)-stylopine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-cheilanthifoline + NADPH + H+ + O2 = (S)-stylopine + NADP+ + 2 H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sanguinarine and macarpine biosynthesis
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Isoquinoline alkaloid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(S)-cheilanthifoline,NADPH:oxygen oxidoreductase (methylenedioxy-bridge-forming)
A heme-thiolate enzyme (P-450) catalysing an oxidative reaction that does not incorporate oxygen into the product. Forms the second methylenedioxy bridge of the protoberberine alkaloid stylopine from oxidative ring closure of adjacent phenolic and methoxy groups of cheilanthifoline.
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CAS REGISTRY NUMBER
COMMENTARY hide
138791-29-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
CYP719A13 can be involved in both sanguinarine and berberine formation in Argemone mexicana
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R,S)-cheilanthifoline + NADPH + H+ + O2
(R,S)-stylopine + NADP+ + 2 H2O
show the reaction diagram
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?
(R,S)-cheilanthifoline + NADPH + H+ + O2
(S)-stylopine + NADP+ + H2O
show the reaction diagram
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both CYP719A2 and CYP719A3 have stylopine synthase activity to catalyze methylenedioxy bridge-formation from cheilanthifoline to stylopine, but not cheilanthifoline synthase activity to convert scoulerine to cheilanthifoline, overview
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?
(S)-cheilanthifoline + NADPH + H+ + O2
(S)-stylopine + NADP+ + H2O
show the reaction diagram
(S)-cheilanthifoline + NADPH + O2
(S)-stylopine + NADP+
show the reaction diagram
(S)-coreximine + NADPH + H+ + O2
(S)-cheilanthifoline + NADP+ + H2O
show the reaction diagram
kcat (S)-coreximine: 1% compared to kcat (S)-cheilanthifoline: 100%
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?
(S)-scoulerine + NADPH + H+ + O2
?
show the reaction diagram
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CYP719A3
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?
(S)-scoulerine + NADPH + O2
(S)-nandinine + NADP+ + H2O
show the reaction diagram
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?
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-tetrahydroberberine + NADP+ + H2O
show the reaction diagram
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?
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
?
show the reaction diagram
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CYP719A3
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(R,S)-cheilanthifoline + NADPH + H+ + O2
(R,S)-stylopine + NADP+ + 2 H2O
show the reaction diagram
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?
(S)-cheilanthifoline + NADPH + H+ + O2
(S)-stylopine + NADP+ + H2O
show the reaction diagram
(S)-cheilanthifoline + NADPH + O2
(S)-stylopine + NADP+
show the reaction diagram
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enzyme is induced 20 h after challenging the cell suspension culture with elicitor
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(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-tetrahydroberberine + NADP+ + H2O
show the reaction diagram
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additional information
?
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the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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the enzyme is a cytochrome P450 dependent monooxygenase
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FAD
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0.004 mM, together with the optimal concentration of NADPH, 0.2 mM, enhances activity by 50%
FMN
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0.004 mM, together with the optimal concentration of NADPH, 0.2 mM, enhances activity by 50%
NADPH
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.032
(R,S)-scoulerine
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CYP719A2 variant, determined with HPLC
0.0004 - 5.2
(S)-cheilanthifoline
0.00054
(S)-scoulerine
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CYP719A3 variant, determined with HPLC
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
kcat (S)-coreximine: 1% compared to kcat (S)-cheilanthifoline: 100%
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000045
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CYP719A3 variant, (S)-scoulerine as substrate, microsomal protein used for determination
additional information
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0.43 pmol/min/pmol P450 for the CYP719A2 variant, (R,S)-scoulerine as substrate; CYP719A2 variant uses only (R,S)-cheilanthifoline as substrate to produce stylopine when incubating with a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates; CYP719A3 and CYP719A2 do not react with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline and magnoflorine to make corresponding products with a methylenedioxy bridge; CYP719A3 but not CYP719A2 variant converts (S)-tetrahydrocolumbamine to (S)-tetrahydroberberine; CYP719A3 converts a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates to stylopine and nandinine
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10
half optimal activity at pH 6.5 and pH 9 using S-cheilanthifoline as a substrate
7 - 9
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about 40% of maximal activity at pH 7 and pH 9
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
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LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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tissue expression patterns of CYP719A2 and CYP719A3, overview
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57450
calculated from cDNA
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
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half-life: 27 h
25
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half-life: 2.3 h
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 15% loss of activity after 4 months
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CYP719A2 and CYP719A3, DNA and amino acid sequence determination and analysis, expression patterns, expression in Saccharomyces cerevisiae microsomes; two full-length P450 cDNAs, CYP719A2 and CYP7193A, expression in Saccharomyces cerevisiae
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expressed in Spodoptera frugiperda Sf9 cells
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.21.1)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)