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Information on EC 2.4.1.170 - isoflavone 7-O-glucosyltransferase and Organism(s) Glycine max and UniProt Accession A6BM07
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2.4.1.170 isoflavone 7-O-glucosyltransferaseIUBMB Comments
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.
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Word Map
- 2.4.1.170
- soybean
-
isoflavonoids
- cotyledon
- daidzin
- kaempferol
- genistin
- 2-hydroxyisoflavanone
-
aglycones
- echinata
-
glycyrrhiza
-
ammonia-lyase
-
phytoalexins
-
long-distance
- luteolin
-
flooding
-
bradyrhizobium
- sojae
-
pueraria
-
cell-suspension
-
phytophthora
-
plant-microbe
- lobata
-
enrei
- naringenin
- glycitin
-
cicer
-
glucosyltransferases
- arietinum
- drug development
The taxonomic range for the selected organisms is: Glycine max
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
gmif7gt, plugt1, isoflavone 7-o-glucosyltransferase, ugt73f1, atgt-2, if7gt, gmugt4, udp-glucose:isoflavone 7-o-glucosyltransferase, isoflavone-specific 7-o-glucosyltransferase, ugt709a4, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
glucosyltransferase, uridine diphosphoglucose-isoflavone 7-O-
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-
-
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UDP-glucose-flavonoid 7-O-glucosyltransferase
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-
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UDP-glucose:isoflavone 7-O-glucosyltransferase
UDPglucose-flavonoid 7-O-glucosyltransferase
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-
-
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UDPglucose:isoflavone 7-O-glucosyltransferase
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-
-
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uridine diphosphoglucose-isoflavone 7-O-glucosyltransferase
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-
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UDP-glucose:isoflavone 7-O-glucosyltransferase
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
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-
-
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PATHWAY SOURCE
PATHWAYS
-
-, -, -, -, -, -
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
97089-62-8
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-glucose + an isoflavone
UDP + an isoflavone 7-O-beta-D-glucoside
-
-
-
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
-
i.e. daidzin
-
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
-
-
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
i.e. genistin
-
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
-
i.e. daidzin
-
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
i.e. genistin
-
?
additional information
?
-
-
GmUGT1 is active with UDP-galactose and UDP-glucuronic acid as substrates. It displays high specific activities toward isoflavones (genistein and daidzein) to produce their 7-O-beta-D-glucosides, it also shows considerable levels of activities toward other flavonoids such as kaempferol, quercetin, naringenin and apigenin. GmUGT1 is also capable of acting on the flavone luteolin, (S)-equol, a 4',7-isoflavandiol, and (R)-equol
-
-
?
additional information
?
-
GmUGT1 is active with UDP-galactose and UDP-glucuronic acid as substrates. It displays high specific activities toward isoflavones (genistein and daidzein) to produce their 7-O-beta-D-glucosides, it also shows considerable levels of activities toward other flavonoids such as kaempferol, quercetin, naringenin and apigenin. GmUGT1 is also capable of acting on the flavone luteolin, (S)-equol, a 4',7-isoflavandiol, and (R)-equol
-
-
?
additional information
?
-
-
none of the following phenolics serve as glucosyl acceptors: cyanidin, trans-p-coumaric acid, caffeic acid, benzoic acid, m- and p-hydroybenzoic acid, salicylic acid, salicyl alcohol and hydroquinone.
-
-
?
additional information
?
-
-
the relative activites for UDP-glucuronic acid and for UDP-galactose is 0% and for UDP-glucose 12%, all tested with genistein as glycosyl acceptor
-
-
?
additional information
?
-
-
in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT3, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
-
-
?
additional information
?
-
in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT3, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
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-
?
additional information
?
-
-
in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT4, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
-
-
?
additional information
?
-
in contrast to GmUGT1, UDP-galactose and UDP-glucuronic acid are essentially inert as substrates for GmUGT4, glucosyl-acceptor substrate specificity, overview. No activity with kaempferol, quercetin, naringenin, apigenin, and luteolin
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-glucose + an isoflavone
UDP + an isoflavone 7-O-beta-D-glucoside
-
-
-
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
-
i.e. daidzin
-
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
i.e. genistin
-
?
UDP-glucose + daidzein
UDP + daidzein 7-O-beta-D-glucoside
-
i.e. daidzin
-
?
UDP-glucose + genistein
UDP + genistein 7-O-beta-D-glucoside
-
i.e. genistin
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
Ca2+, Cd2+, Co2+, Cu2+, Mg2+, Mn2+, Ni2+, Sn2+ or Zn2+ (all at 0.1 mM) have negligible effect on the catalytic activity.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
1 mM EDTA, 1mM uridine, 1 mM UMP, 1 mM UDP, 1 mM UTP, 1 mM glucose, 1 mM diethylpyrocarbonatem or 1 mM phenylmethanesulfonyl fluoride have negligibel effect on the catalytic activity (residual activity, in excess of 64%).
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.253
additional information
additional information
-
as glucosyl acceptor genistein shows the highest activity (100%), daidzein has 73%, formononetin shows 67%, quercetin 32%, kaempferol 19%, 4,2',4',6'-tetrahydoxychalcone 15%, apigenin 14%, aureusidin 5%, esculetin 4% and naringenin shows 3% activity (all tested with UDP-glucose). Enzyme assay is run at pH 8.5 at 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
the expression of UGT4, an isoflavone-specific 7-O-glucosyltransferase (UGT4), is decreased during the reproductive stages. Expression of UGT4 is high in the vegetative stages, and decreased by over 90% during the reproductive stages
additional information
real-time RT-PCR tissue expression analysis of GmIF7GT gene homologues 1-6, overview. The transcript level of a less known gene homologue of isoflavone 7-O-glucosyltransferase GmIF7GT4 is significantly higher by about 11fold, in the roots than the gene homologue mIF7GT1 and the other homologues. Transcript levels of other homologues of GmIF7GT are much lower than the transcript levels of GmIF7GT1 or GmIF7GT4, overview
additional information
-
real-time RT-PCR tissue expression analysis of GmIF7GT gene homologues 1-6, overview. The transcript level of a less known gene homologue of isoflavone 7-O-glucosyltransferase GmIF7GT4 is significantly higher by about 11fold, in the roots than the gene homologue mIF7GT1 and the other homologues. Transcript levels of other homologues of GmIF7GT are much lower than the transcript levels of GmIF7GT1 or GmIF7GT4, overview
additional information
-
the levels of the most abundant GmUGT1 transcripts in cotyledons are much higher than those in lateral roots
additional information
the levels of the most abundant GmUGT1 transcripts in cotyledons are much higher than those in lateral roots
additional information
-
gene GmUGT3 encodes a UGT that is highly specific for isoflavones
additional information
gene GmUGT3 encodes a UGT that is highly specific for isoflavones
additional information
-
gene GmUGT4 encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, followed by taproots, cotyledon, and hypocotyls
additional information
gene GmUGT4 encodes a UGT that is highly specific for isoflavones and is mainly expressed in the lateral roots and seeds, followed by taproots, cotyledon, and hypocotyls
additional information
-
gene GmUGT9 encodes a UGT that is highly specific for isoflavones, the levels of the GmUGT9 transcripts are highest in roots, followed by taproots, cotyledon, and hypocotyls
additional information
gene GmUGT9 encodes a UGT that is highly specific for isoflavones, the levels of the GmUGT9 transcripts are highest in roots, followed by taproots, cotyledon, and hypocotyls
additional information
-
the levels of the most abundant GmUGT7 transcripts in cotyledons are much higher than those in lateral roots
additional information
the levels of the most abundant GmUGT7 transcripts in cotyledons are much higher than those in lateral roots
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
metabolism
physiological function
evolution
metabolism
the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis
physiological function
additional information
metabolism
the enzyme take part in the isoflavonoid pathway, in silico expression profiles of genes involved in the pathway, isoflavonoid pathway overview
metabolism
the isoflavone 7-O-glucosyltransferase is involved in isoflavone conjugate biosynthesis
metabolism
the enzyme is involved in the isoflavone biosynthesis, pathway overview. The expressions of UGT4, an isoflavone-specific 7-O-glucosyltransferase, and of ICHG (isoflavone conjugates hydrolyzing beta-glucosidase) are decreased during the reproductive stages. Isoflavone contents are higher in rhizosphere soil than in bulk soil during both vegetative and reproductive stages, and are comparable in the rhizosphere soil between these two stages
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
physiological function
the enzyme is involved in the synthesis and secretion of isoflavones, e.g. daidzein and genistein, by field-grown soybean. Isoflavone glucosides are secreted into the apoplast. Isoflavones in the rhizosphere soil were shown to induce the expression of rhizobial Nod genes, which initiate the formation of the nodules that fix nitrogen. In addition, isoflavones act as antimicrobial phytoalexins and modulate rhizosphere microbial communities
evolution
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
evolution
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
evolution
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
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
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. Isozyme GmUGT4, but not GmUGT1, plays an exclusive role in the conjugation of isoflavones in the lateral roots of the soybean plant
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). I7GT1_SOYBN
474
0
52036
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D125A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E376A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E392A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
E392D
-
in the mutant the kcat is higher and the Km is lower than in wild type enzyme
E456A
-
in the mutant the kcat is lower and the Km is slightly lower than in wild type enzyme
H15A
-
in the mutant the kcat is lower and the Km is higher than in wild type enzyme
H359A
-
in the mutant the kcat is lower and the Km has the same level as in wild type enzyme
H368A
-
in the mutant the kcat is higher and the Km is higher than in wild type enzyme
additional information
cell engineering by GmIF7GT enzyme 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, Scale up for production using a fermentor
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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.
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning of gene homologues GmIF7GT1-GmIF7GT6, DNA and amino acid sequence determination, expression analysis
gene GmIF7GT, DNA and amino acid sequence determination and analysis, expression analysis
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 GmIF7GT1, quantitative real-time reverse transcription-PCR enzyme expression analysis
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
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Noguchi, A.; Saito, A.; Homma, Y.; Nakao, M.; Sasaki, N.; Nishino, T.; Takahashi, S.; Nakayama, T.
A UDP-glucose:isoflavone 7-O-glucosyltransferase from the roots of soybean (Glycine max) seedlings: Purification, gene cloning, phylogenetics, and an implication for an alternative strategy of enzyme catalysis
J. Biol. Chem.
282
23581-23590
2007
Glycine max
Suita, K.; Kiryu, T.; Sawada, M.; Mitsui, M.; Nakagawa, M.; Kanamaru, K.; Yamagata, H.
Cyclic GMP acts as a common regulator for the transcriptional activation of the flavonoid biosynthetic pathway in soybean
Planta
229
403-413
2009
Glycine max
Livingstone, J.M.; Zolotarov, Y.; Stroemvik, M.V.
Transcripts of soybean isoflavone 7-O-glucosyltransferase and hydroxyisoflavanone dehydratase gene homologues are at least as abundant as transcripts of their well known counterparts
Plant Physiol. Biochem.
49
1071-1075
2011
Glycine max (A6BM07), Glycine max, Glycine max Williams 82 (A6BM07)
Livingstone, J.; Seguin, P.; Strmvik, M.
An in silico study of the genes for the isoflavonoid pathway enzymes in soybean reveals novel expressed homologues
Can. J. Plant Sci.
90
453-469
2010
Glycine max (A6BM07)
Koirala, N.; Pandey, R.P.; Thang, D.V.; Jung, H.J.; Sohng, J.K.
Glycosylation and subsequent malonylation of isoflavonoids in E. coli: strain development, production and insights into future metabolic perspectives
J. Ind. Microbiol. Biotechnol.
41
1647-1658
2014
Glycine max (A6BM07)
Funaki, A.; Waki, T.; Noguchi, A.; Kawai, Y.; Yamashita, S.; Takahashi, S.; Nakayama, T.
Identification of a highly specific isoflavone 7-O-glucosyltransferase in the soybean (Glycine max (L.) Merr.)
Plant Cell Physiol.
56
1512-1520
2015
Glycine max, Glycine max (A6BM07)
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