Information on EC 1.3.3.9 - secologanin synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.3.9
-
RECOMMENDED NAME
GeneOntology No.
secologanin synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
loganin + NADPH + H+ + O2 = secologanin + NADP+ + 2 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C-C bond cleavage
-
-
-
-
oxidation
-
-
-
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redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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camptothecin biosynthesis
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Metabolic pathways
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Monoterpenoid biosynthesis
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secologanin and strictosidine biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
loganin:oxygen oxidoreductase (ring-cleaving)
A heme-thiolate protein (P-450). Secologanin is the precursor of the monoterpenoid indole alkaloids and ipecac alkaloids.
CAS REGISTRY NUMBER
COMMENTARY hide
258339-71-8
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
mutant DELTAthSLS fusion protein forms punctuated aggregates in the cytosol in close vicinity with plastids
metabolism
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the enzyme catalyzes the last step of the monoterpene secoiridoid pathway
additional information
-
the enzyme is anchored to the endoplasmic reticulum via a N-teminal helix, thus allowing the production of secologanin on the cytosolic side of the endoplasmic reticulum membrane
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
loganin + NADPH + H+ + O2
secologanin + NADP+ + 2 H2O
show the reaction diagram
additional information
?
-
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
loganin + NADPH + H+ + O2
secologanin + NADP+ + 2 H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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CYP71A1
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NADPH
-
with NADH only 11.5% of the enzyme activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
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complete inhibition
carbon monoxide
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inhibition by CO and O2 in the ratio 9 to 1 in the dark, can be reversed by illumination with white light
cytochrome c
-
partial inhibition
Metyrapone
-
partial inhibition
miconazole
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partial inhibition
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
enzyme assay
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
leaf epidermal cells are biosynthetically competent to produce secologanin precursors that are converted via many enzymatic transformations to make 16-methoxytabersonine, which is then transported to cells within Catharanthus leaves to complete the last three or four enzymatic transformations to make vindoline
Manually annotated by BRENDA team
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epidermis-specific expression of SLS
Manually annotated by BRENDA team
additional information
-
RT-PCR tissue expression analysis, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
the enzyme is anchored to the endoplasmic reticulum via a N-teminal helix, thus allowing the production of secologanin on the cytosolic side of the endoplasmic reticulum membrane
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of SLS-GFP fusion protein in Catharanthus roseus cells show localization to the endoplasmic reticulum membranes
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
involved in vindoline biosynthesis