Information on EC 1.14.21.12 - (S)-nandinine synthase

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:


The expected taxonomic range for this enzyme is: Eschscholzia californica

EC NUMBER
COMMENTARY hide
1.14.21.12
-
RECOMMENDED NAME
GeneOntology No.
(S)-nandinine synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-scoulerine + NADPH + H+ + O2 = (S)-nandinine + NADP+ + 2 H2O
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sanguinarine and macarpine biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(S)-scoulerine,NADPH:oxygen oxidoreductase [(S)-nandinine-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 (S)-nandinine by the oxidative ring closure of adjacent phenolic and methoxy groups of (S)-scoulerine. cf. EC 1.14.21.2, (S)-cheilanthifoline synthase, which catalyses a similar reaction at the other side of the (S)-scoulerine molecule, forming (S)-cheilanthifoline.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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
-
-
-
?
(R,S)-cheilanthifoline + NADPH + H+ + O2
stylopine + NADP+ + 2 H2O
show the reaction diagram
-
-
-
?
(S)-scoulerine + NADPH + H+ + O2
(S)-nandinine + NADP+ + 2 H2O
show the reaction diagram
-
enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate
-
?
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-tetrahydroberberine + NADP+ + 2 H2O
show the reaction diagram
-
-
-
?
additional information
?
-
no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine
-
-
-
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
Q50LH4
-
-
-
?
(S)-scoulerine + NADPH + H+ + O2
(S)-nandinine + NADP+ + 2 H2O
show the reaction diagram
Q50LH4
-
enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate
-
?
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-tetrahydroberberine + NADP+ + 2 H2O
show the reaction diagram
Q50LH4
-
-
-
?
additional information
?
-
Q50LH4
no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00054
(S)-scoulerine
microsomal protein, pH 7.6, 30°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
30fold higher expression than in leaf
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
sequence contains a putative endoplasmic reticulum-localizing signal
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
treatment with methyl jasmonate induces expression of both CYP719A2 and CYP719A3