Information on EC 2.4.1.236 - flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferase

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The expected taxonomic range for this enzyme is: Citrus

EC NUMBER
COMMENTARY hide
2.4.1.236
-
RECOMMENDED NAME
GeneOntology No.
flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside = UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
transfer of glycosyl group
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
apigenin glycosides biosynthesis
-
-
hesperitin glycoside biosynthesis
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-
luteolin glycosides biosynthesis
-
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naringenin glycoside biosynthesis
-
-
Flavonoid biosynthesis
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Flavone and flavonol biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
UDP-L-rhamnose:flavanone-7-O-glucoside 2''-O-beta-L-rhamnosyltransferase
Acts on the 7-O-glucoside of naringenin and hesperetin, also the flavone 7-O-glucosides of luteolin and apigenin.
CAS REGISTRY NUMBER
COMMENTARY hide
125752-89-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
grapefruit
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-
Manually annotated by BRENDA team
no activity in Citrus reticulata
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
-
the enzyme is involved in the biosynthesis of flavonoid branched-chain glycosides in citrus, overview. 1,2RhaT is the key branch-forming enzyme directing biosynthesis of the bitter flavanone neohesperidoside compounds in bitter Citrus species
additional information
-
flavonois spectrum and levels of Citrus sinensis varieties and tissue distribution, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside
UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
show the reaction diagram
-
-
-
?
UDP-beta-L-rhamnose + naringenin-7-O-glucoside
UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
show the reaction diagram
-
-
-
?
UDP-L-rhamnose + a flavanone 7-O-glucoside
UDP + a flavanone 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
UDP-L-rhamnose + apigenin 7-O-glucoside
UDP + apigenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
-
98% of the activity with hesperetin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
-
-
?
UDP-L-rhamnose + diosmetin 7-O-glucoside
UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
-
a flavone 7-O-glucoside
i.e. neodiosmin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
UDP-L-rhamnose + luteolin 7-O-glucoside
UDP + luteolin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
-
99% of the activity with hesperetin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
-
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
additional information
?
-
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-L-rhamnose + diosmetin 7-O-glucoside
UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
-
a flavone 7-O-glucoside
i.e. neodiosmin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
-
-
i.e. neohesperidin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no metal ion requirement
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ammonium sulfate
-
inhibits the activity of the partially purified enzyme
apigenin 7-O-neohesperidoside
-
0.1 mM, 45% inhibition
bromo-naphthyl-beta-glucopyranoside
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1 mM, 80% inhibition
EGTA
-
weak, 30 mM, 20% inhibition
hesperetin
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1 mM: 66% inhibition, 0.1 mM: 47% inhibition
naringenin
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1 mM: 72% inhibition, 0.1 mM: 54% inhibition
naringin
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weak, 0.1 mM, 12% inhibition
quercetin
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0.1 mM: 93% inhibition, 0.01 mM: 55% inhibition
UDP
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product inhibition, 0.01 mM: 62% inhibition, 0.1 mM: 93% inhibition
UTP
-
0.1 mM, 83% inhibition
additional information
-
not inhibited by neohesperidin, hesperidin, EDTA, arbutin, nitrophenyl-beta-glucopyranoside, nitrophenyl-L-rhamnopyranoside
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0415
hesperetin 7-O-glucoside
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pH 7.5, 37C
0.0024
naringenin 7-O-glucoside
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pH 7.5, 37C
0.0011 - 0.0013
UDP-L-rhamnose
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000624
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pH 7.5, 37C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
young, open
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 52000, recombinant C-terminally His6-Myc-tagged enzyme, SDS-PAGE
monomer
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1 * 50000, SDS-PAGE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8.5
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below pH 6: 90% loss of activity, above pH 8.5: 50% loss of activity
655963
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, 20-50 mM Tris-HCl, pH 7.5, months, stable
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4C, 24 h, over 80% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2735fold
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1,2RhaT cloning and DNA and amino acid sequence determination and analysis, phylogenetic analysis, two native frameshift mutations render the enzyme from orange catalytically inactive
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DNA and amino acid sequence determiation and analysis, phylogenetic analysis, recombinant expression of C-terminally His6-Myc-tagged enzyme in Nicotiana tabacum BY-2 cells
gene 1,2-Rhat, DN and amino acid sequence determination and analysis of in varieties Anliu and Honganliu sweet orange, sequence comparisons
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phylogenetic analysis, 1,2RhaT expressionin BY-2 cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
production of naringin and narirutin from naringenin-7-O-glucoside using the engineered Schizosaccharomyces expressing Arabidopsis thaliana rhamnose synthase 2, AtRHM2, and glycosyltransferases Cm1,2RhaT from Citrus maxima or Cs1,6RhaT from Citrus sinensis as a whole-cell-biocatalyst, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
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the isolation of the rhamnosyltransferase gene may enable its use in genetic engineering directed to modifying grapefruit bitterness
synthesis
metabolically engineered plant cell suspension cultures expressing recombinant Cm1,2RhaT can biotransform hesperetin, the hesperidin aglycone, into neohesperidin