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Information on EC 2.3.1.74 - chalcone synthase and Organism(s) Rubus idaeus and UniProt Accession B0LDU5

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EC Tree
     2 Transferases
         2.3 Acyltransferases
             2.3.1 Transferring groups other than aminoacyl groups
                2.3.1.74 chalcone synthase
IUBMB Comments
The enzyme catalyses the first committed step in the biosynthesis of flavonoids. It can also act on dihydro-4-coumaroyl-CoA, forming phloretin.
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This record set is specific for:
Rubus idaeus
UNIPROT: B0LDU5
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Word Map
The taxonomic range for the selected organisms is: Rubus idaeus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
chalcone synthase, ascl1, ascl2, chs-1, chs_h1, gmirchs, flavanone synthase, ripks4, 6'-deoxychalcone synthase, malonyl-coa:4-coumaroyl-coa malonyltransferase (cyclizing), more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6'-deoxychalcone synthase
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-
-
-
chalcone synthase
-
-
-
-
chalcone synthetase
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-
-
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CHS
-
-
-
-
DOCS
-
-
-
-
flavanone synthase
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-
-
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flavanone synthetase
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-
-
-
naringenin-chalcone synthase
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-
-
-
PKS1
bifunctional enzyme with both chalcone synthase and benzalacetone synthase activity
RinPKS1
bifunctional enzyme with both chalcone synthase and benzalacetone synthase activity
synthase, flavanone
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
The enzyme catalyses the first committed step in the biosynthesis of flavonoids. It can also act on dihydro-4-coumaroyl-CoA, forming phloretin.
CAS REGISTRY NUMBER
COMMENTARY hide
56803-04-4
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-coumaroyl-CoA + 3 malonyl-CoA
naringenin chalcone + 4 CoA + 3 CO2
show the reaction diagram
-
-
-
?
5-hydroxyferulyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
-
-
-
?
caffeoyl-CoA + 3 malonyl-CoA
eriodictyol + 4 CoA + 3 CO2
show the reaction diagram
-
-
-
?
cinnamoyl-CoA + malonyl-CoA
5,7-dihydroxyflavanone + CoA + CO2
show the reaction diagram
-
-
-
?
ferulyl-CoA + malonyl-CoA
homoeriodictyol + CoA + CO2
show the reaction diagram
-
-
-
?
sinapyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
-
-
-
?
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + naringenin chalcone + 3 CO2
show the reaction diagram
4-coumaroyl-CoA + 3 malonyl-CoA
naringenin chalcone + 4 CoA + 3 CO2
show the reaction diagram
RiPKS5 synthesizes naringenin chalcone exclusively
-
-
?
benzoyl-CoA + malonyl-CoA
?
show the reaction diagram
22% activity compared to 4-coumaroyl-CoA
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-
?
caffeoyl-CoA + malonyl-CoA
?
show the reaction diagram
43% activity compared to 4-coumaroyl-CoA
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-
?
cinnamoyl-CoA + malonyl-CoA
?
show the reaction diagram
81% activity compared to 4-coumaroyl-CoA
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-
?
feruloyl-CoA + malonyl-CoA
?
show the reaction diagram
52% activity compared to 4-coumaroyl-CoA
-
-
?
malonyl-CoA + 4-coumaroyl-CoA
naringenin chalcone + CoA + CO2
show the reaction diagram
-
-
PKS1 produces mainly naringenin chalcone as product with small amounts of 4-coumaroyltriacetic acid lactone as byproduct, PKS3 produces mainly 4-coumaroyltriacetic acid lactone and only small amounts of naringenin chalcone
?
additional information
?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01642
4-coumaroyl-CoA
0.02283 - 0.2283
malonyl-CoA
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.045
4-coumaroyl-CoA
0.071
malonyl-CoA
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.742
4-coumaroyl-CoA
3.122
malonyl-CoA
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
calculated from amino acid sequence
6.04
calculated from sequence
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cultivar: Royalty
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
the transcripts of RiPKS4 and RiPKS5 accumulate at a lower level during fruit development in comparison to RiPKS1
Manually annotated by BRENDA team
the transcripts of RiPKS4 and RiPKS5 accumulate at a lower level during fruit development in comparison to RiPKS1
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
PKS4_RUBID
383
0
42256
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42800
43000
89000
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography
PKS3 mutant
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
expressed in Escherichia coli Rosetta-gami (DE3) and BL21-Rosetta (DE3) cells
expression in Escherichia coli
overexpressed in Escherichia coli
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zheng, D.; Schroder, G.; Schroder, J.; Hrazdina, G.
Molecular and biochemical characterization of three aromatic polyketide synthase genes from Rubus idaeus
Plant Mol. Biol.
46
1-15
2001
Rubus idaeus
Manually annotated by BRENDA team
Zheng, D.; Hrazdina, G.
Molecular and biochemical characterization of benzalacetone synthase and chalcone synthase genes and their proteins from raspberry (Rubus idaeus L.)
Arch. Biochem. Biophys.
470
139-145
2008
Rubus idaeus (B0LDU5), Rubus idaeus (B0LDU6)
Manually annotated by BRENDA team
Guo, H.; Yang, Y.; Ma, Y.; Liu, W.; Feng, J.; Luo, Z.; Lu, H.; Liu, C.; Yang, M.; Wang, Y.; Ma, L.
A bifunctional type III polyketide synthase from raspberry (Rubus idaeus L.) with both chalcone synthase and benzalacetone synthase activity
J. Plant Biochem. Biotechnol.
26
80-90
2017
Rubus idaeus (Q8L5L2), Rubus idaeus (Q9AU11)
-
Manually annotated by BRENDA team