Information on EC 1.3.3.9 - secologanin synthase

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The expected taxonomic range for this enzyme is: Catharanthus roseus

EC NUMBER
COMMENTARY hide
1.3.3.9
transferred to EC 1.14.19.62
RECOMMENDED NAME
GeneOntology No.
secologanin synthase
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Monoterpenoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is important in the monoterpenoid indole alkaloid (MIA) biosynthesis in Catharanthus roseus, subcellular organization of the central steps of the pathway, overview. The ring-opening reaction of loganin in the biosynthesis of secologanin is catalyzed by the fourth P450 of this pathway, secologanin synthase (SLS, CYP72A1). Both isozymes SLS1 and SLS2 not only catalyze the oxidative ring cleavage of loganin to produce secologanin but also perform the oxidation of secologanin into secoxyloganin. SLS1 and SLS2 constitute the third type of P450 from the seco-iridoid pathway performing more than one catalytic reaction. Additional enzymes might convert secoxyloganin back to secologanin, the subcellular compartmentation of secologanin biosynthesis may also limit secoxyloganin formation in planta. Secoxyloganin is an acidic compound derived from secologanin that is no longer able to be condensed with tryptamine by STR in the vacuole, due to the absence of the aldehyde function. If secoxyloganin formation occurs in vivo, the resulting depletion of the secologanin pool is deleterious for the subsequent synthesis of MIAs
physiological function
secologanin synthases (SLS) are P450 enzymes that catalyze an unusual ring-opening reaction of loganin in the biosynthesis of the monoterpenoid indole alkaloids (MIA) precursor secologanin
additional information
consensus transcriptome analysis of Catharanthus roseus, detailed overview
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
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?
additional information
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the second secologanin synthase isoform SLS2 produces both secologanin and secoxyloganin
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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
loganin + NADPH + H+ + O2
secologanin + NADP+ + 2 H2O
show the reaction diagram
U5NDT8
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?
additional information
?
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U5NDT8
the second secologanin synthase isoform SLS2 produces both secologanin and secoxyloganin
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
SLS2 might be the prominent isoform of secologanin biosynthesis in the aerial parts of the plant
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
an endoplasmic reticulum-anchored enzyme
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene CYP72C, DNA and amino acid sequence determination and analysis, sequence comparisons, transcriptome analysis, real-time PCR expression analysis