Information on EC 1.14.21.2 - (S)-cheilanthifoline synthase

Word Map on EC 1.14.21.2
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)
Please login to have access to the AMENDA and FRENDA data

The enzyme appears in viruses and cellular organisms

top print hide
EC NUMBER
COMMENTARY hide
1.14.21.2
-
top print hide
RECOMMENDED NAME
GeneOntology No.
(S)-cheilanthifoline synthase
top print hide
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-scoulerine + NADPH + H+ + O2 = (S)-cheilanthifoline + NADP+ + 2 H2O
show the reaction diagram
-
-
-
-
top print hide
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
top print hide
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Isoquinoline alkaloid biosynthesis
-
-
Metabolic pathways
-
-
sanguinarine and macarpine biosynthesis
-
-
top print hide
SYSTEMATIC NAME
IUBMB Comments
(S)-scoulerine,NADPH:oxygen oxidoreductase [(S)-cheilanthifoline-forming]
A cytochrome P-450 (heme-thiolate) enzyme catalysing an oxidative reaction that does not incorporate oxygen into the product. Forms the methylenedioxy bridge of the protoberberine alkaloid cheilanthifoline by the oxidative ring closure of adjacent phenolic and methoxy groups of scoulerine. cf. EC 1.14.21.12, (S)-nandinine synthase, which catalyses a similar reaction at the other side of the (S)-scoulerine molecule, forming (S)-nandinine.
top
top print hide
CAS REGISTRY NUMBER
COMMENTARY hide
138791-27-2
-
top print hide
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
top print hide
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
CYP719A13 can be involved in both sanguinarine and berberine formation in Argemone mexicana
top print hide
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
top print hide
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
-
-
top print hide
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
the enzyme is a cytochrome P450 dependent monooxygenase
-
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
top print hide
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
methyl jasmonate
-
-
top print hide
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0009 - 8.1
(S)-scoulerine
top print hide
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
top print hide
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
top print hide
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
top print hide
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
top print hide
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
top print hide
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
highly expressed
Manually annotated by BRENDA team
top print hide
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
top print hide
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57450
calculated from cDNA
top print hide
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
-
half-life: 30 h
25
-
half-life: 2.5 h
top print hide
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 15% loss of activity after 4 months
-
top print hide
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
yeast microsomal fractions are prepared
-
top print hide
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
-
top print hide
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
methyl jasmonate induces the expression of CYP719A genes in seedlings
-
top
top
top
LINKS TO OTHER DATABASES (specific for EC-Number 1.14.21.2)
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)