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Information on EC 2.4.1.236 - flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferase and Organism(s) Citrus maxima and UniProt Accession Q8GVE3
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EC Tree
2.4.1.236 flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferaseIUBMB Comments
Acts on the 7-O-glucoside of naringenin and hesperetin, also the flavone 7-O-glucosides of luteolin and apigenin.
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Word Map
- 2.4.1.236
- flavonoid
-
bitter
- pummelo
-
orang
- glycosides
- flavones
- rhamnosyltransferases
-
taste
- grapefruit
-
mandarin
- naringin
-
flavor
-
rhamnosylation
- maxima
- glycosyltransferase
- lycopene
-
tasteless
- sinensis
-
non-bitter
- agriculture
- nutrition
- synthesis
- food industry
The taxonomic range for the selected organisms is: Citrus maxima
The expected taxonomic range for this enzyme is: Citrus
The expected taxonomic range for this enzyme is: Citrus
Reaction Schemes
Synonyms
cm1,2rhat, 1,2rhat, 1,2-rhamnosyltransferase, cit1,2rhat, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
rhamnosyltransferase, uridine diphosphorhamnose-flavanone 7-O-glucoside 2''-O-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
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]
acts on the 7-O-glucoside of naringenin and hesperetin, also the flavone 7-O-glucosides of luteolin and apigenin
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
125752-89-8
-
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-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside
UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
-
-
-
?
UDP-beta-L-rhamnose + naringenin-7-O-glucoside
UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
-
-
-
?
UDP-L-rhamnose + a flavanone 7-O-glucoside
UDP + a flavanone 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
glucosylated flavanone is further rhamnosylated by a rhamnosyltransferase using UDP-rhamnose
-
-
?
UDP-L-rhamnose + apigenin 7-O-glucoside
UDP + apigenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
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]
-
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]
UDP-L-rhamnose + luteolin 7-O-glucoside
UDP + luteolin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
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]
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. neohesperidin
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. neohesperidin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
enzyme catalyzes the transfer of rhamnose from UDP-rhamnose to the C-2 hydroxyl group of glucose attached via C-7-O- of naringenin or hesperetin, lower activity than with naringenin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
i.e. neohesperidin
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
a flavanone 7-O-glucoside
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]
-
-
i.e. naringin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, endogenous substrate, flavonoid biosynthetic pathway
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, natural substrate
-
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, natural substrate, enzyme catalyzes the transfer of rhamnose from UDP-rhamnose to the C-2 hydroxyl group of glucose attached via C-7-O- of naringenin or hesperetin, best substrate, 141% of the activity with hesperetin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
a flavanone 7-O-glucoside
i.e. naringin, a bitter 7-O-neohesperidoside
-
?
additional information
?
-
-
enzyme catalyzes the production of bitter flavanone-glucosides
-
-
?
additional information
?
-
-
not: flavonoid 5-O-glucosides or aglycones, naringenin, hesperetin, quercetin, UDP-glucose, UDP-galactose, UDP-glucoronic acid
-
-
?
additional information
?
-
-
the enzyyme specifically catalyzes rhamnosylation of flavanone-7-O-glucose and flavone-7-O-glucose substrates at position 2 of the glucose moiety
-
-
?
additional information
?
-
-
the enzyme also catalyzes the rhamnosylation of diosmetin 7-O-glucoside at position 2 of the glucose moiety to give neodiosmin, but Cm1,2RhaT is specific for flavonoid-7-O-glucosides and utilizes no flavonoid-3-O-glucosides
-
-
?
additional information
?
-
Cm1,2RhaT has glycosyl transfer activity toward UDP-xylose as well as UDP-rhamnose, it is a branch-forming rhamnosyltransferase, substrate specificity of the recombinant enzyme, overview. No activity with quercetin-3-O-glucoside
-
-
?
additional information
?
-
-
Cm1,2RhaT has glycosyl transfer activity toward UDP-xylose as well as UDP-rhamnose, it is a branch-forming rhamnosyltransferase, substrate specificity of the recombinant enzyme, overview. No activity with quercetin-3-O-glucoside
-
-
?
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-L-rhamnose + diosmetin 7-O-glucoside
UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
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]
-
-
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]
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. naringin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, endogenous substrate, flavonoid biosynthetic pathway
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, natural substrate
-
-
?
additional information
?
-
-
enzyme catalyzes the production of bitter flavanone-glucosides
-
-
?
additional information
?
-
-
the enzyyme specifically catalyzes rhamnosylation of flavanone-7-O-glucose and flavone-7-O-glucose substrates at position 2 of the glucose moiety
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
not inhibited by neohesperidin, hesperidin, EDTA, arbutin, nitrophenyl-beta-glucopyranoside, nitrophenyl-L-rhamnopyranoside
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
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). FLRT_CITMA
452
0
51236
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
52000
52000
x * 52000, recombinant C-terminally His6-Myc-tagged enzyme, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 52000, recombinant C-terminally His6-Myc-tagged enzyme, SDS-PAGE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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
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
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
metabolically engineered plant cell suspension cultures expressing recombinant Cm1,2RhaT can biotransform hesperetin, the hesperidin aglycone, into neohesperidin
nutrition
-
the isolation of the rhamnosyltransferase gene may enable its use in genetic engineering directed to modifying grapefruit bitterness
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lewinsohn, E.; Britsch, L.; Mazur, Y.; Gressel, J.
Flavanone glycoside biosynthesis in Citrus. Chalcone synthase, UDP-glucose: flavanone-7-O-glucosyltransferase and -rhamnosyltransferase activities in cell-free extracts
Plant Physiol.
91
1323-1328
1989
Citrus maxima, Citrus x paradisi
Bar-Peled, M.; Lewinsohn, E.; Fluhr, R.; Gressel, J.
UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus
J. Biol. Chem.
266
20953-20959
1991
Citrus maxima
Frydman, A.; Weisshaus, O.; Huhman, D.V.; Sumner, L.W.; Bar-Peled, M.; Lewinsohn, E.; Fluhr, R.; Gressel, J.; Eyal, Y.
Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of the low-calorie sweetener and flavor enhancer NHDC
J. Agric. Food Chem.
53
9708-9712
2005
Citrus maxima (Q8GVE3)
Frydman, A.; Liberman, R.; Huhman, D.V.; Carmeli-Weissberg, M.; Sapir-Mir, M.; Ophir, R.; W Sumner, L.; Eyal, Y.
The molecular and enzymatic basis of bitter/non-bitter flavor of citrus fruit: evolution of branch-forming rhamnosyltransferases under domestication
Plant J.
73
166-178
2013
Citrus maxima, Citrus sinensis, Citrus sinensis valencia, no activity in Citrus reticulata
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