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Information on EC 2.3.1.74 - chalcone synthase and Organism(s) Glycine max and UniProt Accession P30081

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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:
Glycine max
UNIPROT: P30081
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The taxonomic range for the selected organisms is: Glycine max
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
chalcone synthase, ascl1, ascl2, chs-1, chs_h1, gmirchs, flavanone synthase, ripks4, malonyl-coa:4-coumaroyl-coa malonyltransferase (cyclizing), chs-7, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6'-deoxychalcone synthase
-
-
-
-
chalcone synthase
-
-
-
-
chalcone synthase 6
-
chalcone synthase 7
-
chalcone synthetase
-
-
-
-
CHS
-
-
-
-
chs-1
-
isoform
CHS-7
-
isoform
DOCS
-
-
-
-
flavanone synthase
-
-
-
-
flavanone synthetase
-
-
-
-
naringenin-chalcone synthase
-
-
-
-
naringenin-chalcone synthase 6
-
synthase, flavanone
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
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
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
-
-
-
?
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
-
15% of the reaction rate with 4-coumaroyl-CoA
i.e. pinocembrin
?
ferulyl-CoA + malonyl-CoA
homoeriodictyol + CoA + CO2
show the reaction diagram
-
reaction gives one major and 3 minor reaction products, none of those is identical with homoeriodictyol
-
-
?
malonyl CoA + 4-coumaroyl-CoA + NADH
6'-deoxychalcone + CoA + CO2 + NAD+
show the reaction diagram
-
-
the formation of this product requires an additional reductase
?
malonyl-CoA + 4-coumaroyl-CoA
naringenin chalcone + CoA + CO2
show the reaction diagram
malonyl-CoA + 4-coumaroyl-CoA + NADPH
5'-deoxyflavanone + CoA + CO2 + NADP+
show the reaction diagram
-
-
the formation of this product requires an additional reductase
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + naringenin chalcone + 3 CO2
show the reaction diagram
-
-
-
-
?
additional information
?
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
type IV chalcone isomerase-like protein (CHIL) binds to the enzyme to serve as a rectifier - rather than an activator - of promiscuous enzyme; it enhances enzyme-catalyzed THC production and diminishes CTAL formation without enhancing total polyketide production, thereby facilitating the efficient influx of substrates from the general phenylpropanoid pathway to the flavonoid pathway
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.017
NADPH
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0085
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
-
caffeoyl-CoA
7.5
-
4-coumaroyl-CoA
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
L. Merr. cv RCAT Angora (3150 CHU) and cv Harovinton (3100 CHU)
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
expression patterns is higher at 70 d after pollination in both the cultivars. Expression of the gene coincides with the onset of accumulation of isoflavonoids in the embryos. CHS7 is expressed at significantly greater level in RCAT Angora than in Harovinton
Manually annotated by BRENDA team
expression patterns is higher at 70 d after pollination in both the cultivars. Expression of the gene coincides with the onset of accumulation of isoflavonoids in the embryos. CHS8 is expressed at significantly greater level in RCAT Angora than in Harovinton
Manually annotated by BRENDA team
hairy roots, transformed with the soybean chalcone synthase (CHS6) or isoflavone synthase (IFS2) genes, with dramatically decreased capacity to synthesize isoflavones are produced to determine what effects these changes would have on susceptibility to a fungal pathogen. Blockage of isoflavone synthesis by constitutive expression of two key genes in the isoflavonoid pathway, chalcone synthase and isoflavone synthase leads to the inability to synthesize glyceollin in soybean hairy roots on root resistance to Fusarium solani f. sp. glycines
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
CHS7_SOYBN
389
0
42874
Swiss-Prot
other Location (Reliability: 5)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
-
2 * 40000, SDS-PAGE
75000
-
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 45000, SDS-PAGE
dimer
-
2 * 40000, SDS-PAGE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21 cells
-
hairy roots, transformed with the soybean chalcone synthase (CHS6) or isoflavone synthase (IFS2) genes, with dramatically decreased capacity to synthesize isoflavones are produced to determine what effects these changes would have on susceptibility to a fungal pathogen
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Welle, R.; Grisebach, H.
Isolation of a novel NADPH-dependent reductase which coacts with chalcone synthase in the biosynthesis of 6'-deoxychalcone
FEBS Lett.
236
221-225
1988
Glycine max
-
Manually annotated by BRENDA team
Schrder, J.; Schrder, G.
Stilbene and chalcone synthases: Related enzymes with key functions in plant-specific pathways
Z. Naturforsch. C
45c
1-8
1990
Arabidopsis thaliana, Glycine max, Sinapis alba
-
Manually annotated by BRENDA team
Welle, R.; Grisebach, H.
Purification and properties of chalcone synthase from cell suspension cultures of soybean
Z. Naturforsch. C
42c
1200-1206
1987
Glycine max
-
Manually annotated by BRENDA team
Dhaubhadel, S.; Gijzen, M.; Moy, P.; Farhangkhoee, M.
Transcriptome analysis reveals a critical role of CHS7 and CHS8 genes for isoflavonoid synthesis in soybean seeds
Plant Physiol.
143
326-338
2007
Glycine max (P30081), Glycine max (Q84V87), Glycine max
Manually annotated by BRENDA team
Lozovaya, V.V.; Lygin, A.V.; Zernova, O.V.; Ulanov, A.V.; Li, S.; Hartman, G.L.; Widholm, J.M.
Modification of phenolic metabolism in soybean hairy roots through down regulation of chalcone synthase or isoflavone synthase
Planta
225
665-679
2007
Glycine max (P30080), Glycine max
Manually annotated by BRENDA team
Kasai, A.; Kasai, K.; Yumoto, S.; Senda, M.
Structural features of GmIRCHS, candidate of the I gene inhibiting seed coat pigmentation in soybean: implications for inducing endogenous RNA silencing of chalcone synthase genes
Plant Mol. Biol.
64
467-479
2007
Glycine max (Q6X0M8), Glycine max
Manually annotated by BRENDA team
Waki, T.; Mameda, R.; Nakano, T.; Yamada, S.; Terashita, M.; Ito, K.; Tenma, N.; Li, Y.; Fujino, N.; Uno, K.; Yamashita, S.; Aoki, Y.; Denessiouk, K.; Kawai, Y.; Sugawara, S.; Saito, K.; Yonekura-Sakakibara, K.; Morita, Y.; Hoshino, A.; Takahashi, S.; Nakayama, T.
A conserved strategy of chalcone isomerase-like protein to rectify promiscuous chalcone synthase specificity
Nat. Commun.
11
870
2020
Antirrhinum majus, Glycine max
Manually annotated by BRENDA team