Information on EC 1.14.21.2 - (S)-cheilanthifoline synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.21.2
-
RECOMMENDED NAME
GeneOntology No.
(S)-cheilanthifoline synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-scoulerine + NADPH + H+ + O2 = (S)-cheilanthifoline + NADP+ + 2 H2O
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
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)-scoulerine,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 methylenedioxy bridge of the protoberberine alkaloid cheilanthifoline from oxidative ring closure of adjacent phenolic and methoxy groups of scoulerine.
CAS REGISTRY NUMBER
COMMENTARY hide
138791-27-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
CYP719A13 can be involved in both sanguinarine and berberine formation in Argemone mexicana
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-coreximine + NADPH + H+ + O2
(S)-cheilanthifoline + NADP+ + H2O
show the reaction diagram
kcat (S)-coreximine: 1% compared to kcat (S)-cheilanthifoline: 100%
-
-
?
(S)-scoulerine + NADPH + H+ + O2
(S)-cheilanthifoline + NADP+ + H2O
show the reaction diagram
(S)-scoulerine + NADPH + H+ + O2
(S)-nandinine + NADP+ + H2O
show the reaction diagram
-
-
-
?
(S)-scoulerine + NADPH + O2
(S)-cheilanthifoline + NADP+
show the reaction diagram
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
(S)-scoulerine + NADPH + H+ + O2
(S)-cheilanthifoline + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(S)-scoulerine + NADPH + O2
(S)-cheilanthifoline + NADP+
show the reaction diagram
-
enzyme is induced 20 h after challenging the cell suspension cultur with elicitor
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
the enzyme is a cytochrome P450 dependent monooxygenase
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FAD
-
0.004 mM, together with the optimal concentration of NADPH, 0.2 mM, enhances activity by 50%
FMN
-
0.004 mM, together with the optimal concentration of NADPH, 0.2 mM, enhances activity by 50%
NADPH
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
methyl jasmonate
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-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0009 - 8.1
(S)-scoulerine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 10
half optimal activity at pH 6.5 and 8.5; half optimal activity at pH 6.5 and pH 9 using S-cheilanthifoline as a substrate
7 - 9
-
about 50% of maximal activity at pH 7 and pH 9
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
highly expressed
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57450
calculated from cDNA
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
-
half-life: 30 h
25
-
half-life: 2.5 h
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 15% loss of activity after 4 months
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
yeast microsomal fractions are prepared
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Spodoptera frugiperda Sf9 cells
into the pT7Blue T-vector for sequencing, and subcloned into a yeast expression vector
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
methyl jasmonate induces the expression of CYP719A genes in seedlings
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