Information on EC 1.14.21.12 - (S)-nandinine synthase

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The expected taxonomic range for this enzyme is: Eschscholzia californica

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EC NUMBER
COMMENTARY hide
1.14.21.12
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RECOMMENDED NAME
GeneOntology No.
(S)-nandinine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-scoulerine + NADPH + H+ + O2 = (S)-nandinine + NADP+ + 2 H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sanguinarine and macarpine biosynthesis
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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.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
stylopine + NADP+ + 2 H2O
show the reaction diagram
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?
(S)-scoulerine + NADPH + H+ + O2
(S)-nandinine + NADP+ + 2 H2O
show the reaction diagram
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enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate
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?
(S)-tetrahydrocolumbamine + NADPH + H+ + O2
(S)-tetrahydroberberine + NADP+ + 2 H2O
show the reaction diagram
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?
additional information
?
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no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine
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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
Q50LH4
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-
-
?
(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
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-
?
additional information
?
-
Q50LH4
no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00054
(S)-scoulerine
microsomal protein, pH 7.6, 30°C
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
30fold higher expression than in leaf
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
sequence contains a putative endoplasmic reticulum-localizing signal
Manually annotated by BRENDA team
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
treatment with methyl jasmonate induces expression of both CYP719A2 and CYP719A3
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.21.12)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)