Information on EC 2.4.1.170 - isoflavone 7-O-glucosyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.170
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RECOMMENDED NAME
GeneOntology No.
isoflavone 7-O-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + an isoflavone = UDP + an isoflavone 7-O-beta-D-glucoside
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
biochanin A conjugates interconversion
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daidzein conjugates interconversion
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formononetin conjugates interconversion
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genistein conjugates interconversion
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Isoflavonoid biosynthesis
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maackiain conjugates interconversion
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medicarpin conjugates interconversion
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
The 4'-methoxy isoflavones biochanin A and formononetin and, more slowly, the 4'-hydroxyisoflavones genistein and daidzein, can act as acceptors. The enzyme does not act on isoflavanones, flavones, flavanones, flavanols or coumarins.
CAS REGISTRY NUMBER
COMMENTARY hide
97089-62-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Swissprot
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
cv Elsanta
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Manually annotated by BRENDA team
six gene homologues GmIF7GT1-GmIF7GT6
Uniprot
Manually annotated by BRENDA team
putative glucosyltransferase-2; subsp. japonica
UniProt
Manually annotated by BRENDA team
collected from Langxi County, Anhui Province, China, gene PlUGT1
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
nine different GmUGT cDNAs that are related to GmUGT1 are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview. The enzymes of subgroup A, GmUGT3, GmUGT4, and GmUGT9, all are highly specific for isoflavones. Gene GmUGT4, a representative of subgroup A, encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, while gene GmUGT1, a representative of subgroup B, encodes an enzyme displaying a broad glucosyl-acceptor specificity and is expressed in the aerial parts, i.e. cotyledons, hypocotyls and pods; nine different GmUGT cDNAs that are related to GmUGT1, UniProt ID A6BM07, are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview; nine different GmUGT cDNAs that are related to GmUGT1, UniProt ID A6BM07, are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview. The enzymes of subgroup A, GmUGT3, GmUGT4, and GmUGT9, all are highly specific for isoflavones; nine different GmUGT cDNAs that are related to GmUGT1, UniProt ID A6BM07, are obtained, some of which are classified into two phylogenetically different subgroups, phylogenetic analysis, overview. The enzymes of subgroup A, GmUGT3, GmUGT4, and GmUGT9, all are highly specific for isoflavones. Gene GmUGT4, a representative of subgroup A, encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, while gene GmUGT1, a representative of subgroup B, encodes an enzyme displaying a broad glucosyl-acceptor specificity and is expressed in the aerial parts, i.e. cotyledons, hypocotyls and pods
metabolism
physiological function
the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis. Isoflavone conjugates, 7-O-beta-D-glucosides and 7-O-(6''-malonyl-beta-D-glucosides) of daidzein and genistein, accumulate in soybean roots and serve as the stored precursors of isoflavones (aglycons), which play very important roles in the rhizobia-mediated nodulation of this plant; the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis. Isoflavone conjugates, 7-O-beta-D-glucosides and 7-O-(6''-malonyl-beta-D-glucosides) of daidzein and genistein, accumulate in soybean roots and serve as the stored precursors of isoflavones (aglycons), which play very important roles in the rhizobia-mediated nodulation of this plant; the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis. Isoflavone conjugates, 7-O-beta-D-glucosides and 7-O-(6''-malonyl-beta-D-glucosides) of daidzein and genistein, accumulate in soybean roots and serve as the stored precursors of isoflavones (aglycons), which play very important roles in the rhizobia-mediated nodulation of this plant. Isozyme GmUGT4, but not GmUGT1, plays an exclusive role in the conjugation of isoflavones in the lateral roots of the soybean plant
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-glucose + 4,2',4',6'-tetrahydroxychalcone
UDP + ?
show the reaction diagram
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-
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?
UDP-glucose + apigenin
UDP + apigenin 7-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
UDP-glucose + aureusidin
UDP + aureusidin 6-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
UDP-glucose + baicalein
UDP + baicalein 7-O-beta-D-glucoside
show the reaction diagram
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very low activity
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-
?
UDP-glucose + biochanin A
UDP + biochanin A 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + eriodictyol
UDP + eriodictyol 7-O-beta-D-glucoside
show the reaction diagram
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-
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UDP-glucose + esculetin
UDP + esculetin 7-O-beta-D-glucoside
show the reaction diagram
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-
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-
?
UDP-glucose + ferulic acid
UDP + ferulic acid 7-O-beta-D-glucoside
show the reaction diagram
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low activity
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-
?
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + isoliquiritigenin |
UDP + isoliquiritigenin 7-O-beta-D-glucoside
show the reaction diagram
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-
-
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?
UDP-glucose + isovitexin
UDP + isovitexin 7-O-beta-D-glucoside
show the reaction diagram
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-
?
UDP-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + liquiritigenin
UDP + liquiritigenin 7-O-beta-D-glucoside
show the reaction diagram
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very low activity
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?
UDP-glucose + naringenin
UDP + naringenin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + salicylic acid
UDP + salicylic acid 7-O-beta-D-glucoside
show the reaction diagram
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very low activity
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?
UDP-glucose + scopoletin
UDP + scopoletin 7-O-beta-D-glucoside
show the reaction diagram
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low activity
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?
additional information
?
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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
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
show the reaction diagram
UDP-glucose + formononetin
UDP + formononetin 7-O-beta-D-glucoside
show the reaction diagram
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i.e. ononin
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?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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Ca2+, Cd2+, Co2+, Cu2+, Mg2+, Mn2+, Ni2+, Sn2+ or Zn2+ (all at 0.1 mM) have negligible effect on the catalytic activity.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Fe2+
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0.1 mM, residual activity 28%
Hg2+
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0.1 mM, residual activity 26%
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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the enzyme is stress-inducible, transient induction by cell suspension culture treatment with yeast extract
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.012
Biochanin A
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0.00042 - 0.0985
daidzein
0.018
eriodictyol
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0.024
formononetin
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0.00031 - 0.06
genistein
0.0263
kaempferol
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0.0353
quercetin
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0.024 - 2.1
UDP-glucose
0.2
UDPglucose
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1 - 5.89
daidzein
0.0004 - 6.04
genistein
0.11 - 8.79
UDP-glucose
additional information
additional information
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
37 - 304
daidzein
848
54 - 409
genistein
377
0.25 - 164
UDP-glucose
64
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.045
substrate genistein, pH 8.5, 30°C, purified recombinant enzyme
0.049
substrate daidzein, pH 8.5, 30°C, purified recombinant enzyme
0.158
substrate genistein, pH 8.5, 30°C, purified recombinant enzyme
0.209
substrate genistein, pH 8.5, 30°C, purified recombinant enzyme
0.253
substrate daidzein, pH 8.5, 30°C, purified recombinant enzyme; substrate genistein, pH 8.5, 30°C, purified recombinant enzyme
0.457
substrate daidzein, pH 8.5, 30°C, purified recombinant enzyme
0.465
substrate genistein, pH 8.5, 30°C, purified recombinant enzyme
0.467
substrate daidzein, , pH 8.5, 30°C, purified recombinant enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.6
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conversion rate about 13%
8.5 - 9
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8.8
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conversion rate about 10%
7 - 9
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active over this pH range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.6
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sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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seedling
Manually annotated by BRENDA team
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during the riping process the enzyme shows two activity peaks: in green fruits and in full-ripe red fruits
Manually annotated by BRENDA team
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unifoliate nodes, seedling
Manually annotated by BRENDA team
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exocarp, mesocarp and endocarp
Manually annotated by BRENDA team
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seedling
Manually annotated by BRENDA team
AtGT-2 is expressed in this tissue, higher in the flowers and leaves than in roots and stems
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42000
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sucrose density gradient ultracentrifugation
45000
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SDS-PAGE
46000
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gel filtration chromatography
48700
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x * 48700, about, DNA sequence calculation
50000
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gel filtration
54000
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x * 54000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10
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at 20°C for 8 h
674845
8.5 - 9
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optimal stability
488802
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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below 30°C at pH 8.5 for 1h
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2-mercaptoethanol, 40 mM, stabilizes during purification
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dithioerythritol, 10 mM, effectively stabilizes during purification
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 20% v/v glycerol, stable for several months
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE-Sepharose Fast Flow column, Q-Sepharose HP column, Phenyl-Sepharose HP column (pH 8.5), hydroxyapatite column, gel filtration (HiLoad 26/60 Superdex 200pg column), resource Q column and chromatofocusing on Mono P (Mono P column), all at 4°C. The activity in the crude extract is extremely unstable to oxidation and the addition of 2-mercaptoethanol is essential for its efficient purification. The addition of CHAPS to purification buffers is also essential for purification after step 6 (hydroxyapatite chromatography), otherwise the activity is irreversibly lost.
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recombinant enzyme from Escherichia coli
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recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) to near homogeneity by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning of gene homologues GmIF7GT1-GmIF7GT6, DNA and amino acid sequence determination, expression analysis
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DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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expressed in Escherichia coli
expressed in Escherichia coli BL21(DE3)
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gene GmIF7GT, DNA and amino acid sequence determination and analysis, expression analysis
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gene GmIF7GT, recombinant functional expression in Escherichia coli strain BL21(DE3), coexpression with acyl-CoA carboxylase alpha and beta subunits, biotin ligase, and acetyl-CoA synthetase from Nocardia farcinia for subsequent malonylization of the reaction product of GmIF7GT-encoded isoflavone 7-O-glucosyltransferase. The isoflavonoids are glycosylated at position 7 by 7-O-glycosyltranferase and are further malonylated at position 6' of glucose by malonyl-CoA:isoflavone 7-O-glucoside-6'-O-malonyltransferase both from Glycine max
gene GmUGT1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis; gene GmUGT3, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis; gene GmUGT4, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis; gene GmUGT7, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis; gene GmUGT9, DNA and amino acid sequence determination and analysis, phylogenetic analysis, genotyping, quantitative real-time RT-PCR enzyme expression analysis
gene PlUGT1 or UGT88E12, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli and in Saccharomyces cerevisiae strain WAT11
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glutathione S-transferase fusion protein expressed in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is dramatically stimulated by 0.05 mM 8-bromo-cGMP
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the enzyme is strongly induced by methyl jasmonate signal in cell suspension culture
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D125A
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in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E376A
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in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E392A
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in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E392D
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in the mutant the kcat is higher and the Km is lower than in wild type enzyme
E456A
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in the mutant the kcat is lower and the Km is slightly lower than in wild type enzyme
H15A
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in the mutant the kcat is lower and the Km is higher than in wild type enzyme
H359A
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in the mutant the kcat is lower and the Km has the same level as in wild type enzyme
H368A
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in the mutant the kcat is higher and the Km is higher than in wild type enzyme
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
isoflavonoids and their glycosides may prove useful as anticancer drugs with added advantage of increased solubility, stability and bioavailability. Among the six compounds tested, genistein most effectively inhibits the growth of B16F10 and AGS cells, with IC50 values of 0.0077 mM and 0.0398 mM, respectively. Unlike derivatives of genistein (genistin and biochanin A), the glycosylated and methylated forms of daidzein (daidzin and formononetin) exhibit more effective growth inhibition than aglycon, daidzein