Information on EC 2.3.1.146 - pinosylvin synthase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
2.3.1.146
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RECOMMENDED NAME
GeneOntology No.
pinosylvin synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + cinnamoyl-CoA = 4 CoA + pinosylvin + 4 CO2
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
pinosylvin metabolism
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Stilbenoid, diarylheptanoid and gingerol biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:cinnamoyl-CoA malonyltransferase (cyclizing)
Not identical with EC 2.3.1.74 (naringenin-chalcone synthase) or EC 2.3.1.95 (trihydroxystilbene synthase).
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CAS REGISTRY NUMBER
COMMENTARY hide
72994-49-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Japanese red pine, three isoenzymes PDSTS1, PDSTS2 and PDSTS3
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Manually annotated by BRENDA team
D. Don
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Manually annotated by BRENDA team
Eastern white pine, two encoding genes STS1 and STS2, STS1 has only 3-5% of activity of STS2
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Manually annotated by BRENDA team
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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
4-hydroxycinnamoyl-CoA + malonyl-CoA
cis-2-acetylresveratrol + CoA + CO2
show the reaction diagram
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-
-
?
caffeoyl-CoA + malonyl-CoA
piceatannol + CoA + CO2
show the reaction diagram
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-
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-
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
show the reaction diagram
dihydrocinnamoyl-CoA + 3 malonyl-CoA
dihydropinosylvin + 4 CoA + 4 CO2
show the reaction diagram
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-
-
-
?
feruloyl-CoA + malonyl-CoA
rhapontigenin + CoA + CO2
show the reaction diagram
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-
-
-
?
p-coumaroyl-CoA + malonyl-CoA
2-malonylresveratrol + CoA + CO2
show the reaction diagram
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-
-
?
p-coumaroyl-CoA + malonyl-CoA
resveratrol + CoA + CO2
show the reaction diagram
phenylpropionyl-CoA + malonyl-CoA
?
show the reaction diagram
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-
-
-
?
phenylpropionyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
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?
additional information
?
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enzyme does not precisely control the number of condensations leading to diverse products
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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
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
show the reaction diagram
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pinosylvin
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potent inhibitor of isozyme PDSTS2 and PDSTS3, noncompetitive
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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maximal response to treatment with conidia Botrytis cinerea after 35 h; maximal response to treatment with UV-light of PST-1 after 20 h
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0004 - 0.0038
cinnamoyl-CoA
0.006 - 0.024
malonyl-CoA
0.0009 - 0.0053
p-Coumaroyl-CoA
0.003 - 0.008
phenylpropionyl-CoA
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-
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.013 - 0.152
pinosylvin
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
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isozyme STS1
8
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reaction with p-coumaroyl-CoA, isozymes PDSTS2 and PDSTS3
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35000
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isozyme PDSTS3, SDS-PAGE
42000
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isozymes PDSTS1 and PDSTS2, SDS-PAGE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
of recombinant enzymes
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a male cone-specific promoter from Pinus radiata D. Don is used to express a stilbene synthase gene in anthers of transgenic Nicotiana tabacum plants, resulting in complete male sterility in 70% of the transformed plants
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expressed in Escherichia coli
expressed in Escherichia coli JM109
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expressed in Escherichia coli; transfected into Nicotiana tabacum cv. Petit Havana SR1
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pinosylvin-synthase-encoding gene from Pinus sylvestris is transferred into aspen (Populus tremula) and two hybrid aspen clones (Populus tremula tremuloides) by Agrobacterium tumefaciens mediated transformation. Transgenic plants accumulated pinosylvin synthase-specific mRNA and showed stilbene synthase enzyme activity in vitro. Transgenic aspen line H4 showed increased resistance to Phellinus tremulae, while two hybrid aspen transformants decayed faster than the control trees. No accumulation of stilbenes in the transgenic plantlets
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pss from Pinus sylvestris are stably transformed into bread wheat. The expression of the target genes is regulated by stress-inducible grapevine promoters. pss Transgenic lines accumulate stilbene derivatives upon induction by UV light. None of the four tested pss expressing lines showes an increased fungal resistance
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.146)
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)