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Information on EC 2.4.1.358 - acylphloroglucinol glucosyltransferase
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EC Tree
2.4.1.358 acylphloroglucinol glucosyltransferaseSpecify your search results
The expected taxonomic range for this enzyme is: Fragaria x ananassa
Reaction Schemes
Synonyms
ugt71k3, ugt71k3a, udp-glucose:apg glucosyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
UGT71K3
UGT71K3a
UGT71K3b
UGT71K3
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + 2-acylphloroglucinol = UDP + 2-acylphloroglucinol 1-O-beta-D-glucoside
-
-
-
-
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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-alpha-D-glucose + 1-naphthol
UDP + naphthalen-1-yl beta-D-glucopyranoside
-
-
-
-
?
UDP-alpha-D-glucose + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
UDP + 3,5-dihydroxy-4-(2-methylpropanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-2-(2-methylpropanoyl)phenyl beta-D-glucopyranoside
UDP-alpha-D-glucose + 2-naphthol
UDP + naphthalen-2-yl beta-D-glucopyranoside
-
both allelic proteins of UGT71K3a/b prefer 2-naphthol and 1-naphthol
-
-
?
UDP-alpha-D-glucose + 3-hydroxycoumarin
UDP + 2-oxo-2H-1-benzopyran-3-yl beta-D-glucopyranoside
-
-
-
-
?
UDP-alpha-D-glucose + 3-hydroxyflavone
UDP + 3-[(beta-D-glucopyranosyl)oxy]flavone
-
-
-
-
?
UDP-alpha-D-glucose + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
UDP + 3,5-dihydroxy-2-(3-methylbutanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-4-(3-methylbutanoyl)phenyl beta-D-glucopyranoside
UDP-alpha-D-glucose + 4-hydroxy-2,5-dimethyl-3(2H)-furanone
UDP + 2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl beta-D-glucopyranoside
the enzyme catalyzes the glucosylation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone, the key strawberry flavor compound in strawberry fruit. UGT71K3b is the more efficient enzyme compared with UGT71K3a for the glucosylation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone
-
-
?
UDP-alpha-D-glucose + 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone
UDP + 2-ethyl-5-methyl-4-oxo-4,5-dihydrofuran-3-yl beta-D-glucopyranoside
-
-
-
?
UDP-alpha-D-glucose + 5-hydroxyflavone
UDP + 5-[(beta-D-glucopyranosyl)oxy]flavone
-
poor substrate
-
-
?
UDP-alpha-D-glucose + 6-hydroxycoumarin
UDP + 2-oxo-2H-1-benzopyran-6-yl beta-D-glucopyranoside
-
-
-
-
?
UDP-alpha-D-glucose + 7-hydroxycoumarin
UDP + 2-oxo-2H-1-benzopyran-7-yl beta-D-glucopyranoside
-
-
-
-
?
UDP-alpha-D-glucose + 7-hydroxyflavone
UDP + 7-[(beta-D-glucopyranosyl)oxy]flavone
-
-
-
-
?
UDP-alpha-D-glucose + acetylphloroglucinol
UDP + 2-acetylphloroglucinol 1-O-beta-D-glucoside
-
-
-
-
?
UDP-alpha-D-glucose + benzoic acid
?
UGT71K3a/b exhibits minor catalytic activity toward benzoic acid (6-10% relative activity). Other alcohols are not converted (less than 3%)
-
-
?
UDP-alpha-D-glucose + scopoletin
UDP + 6-methoxy-2-oxo-2H-1-benzopyran-7-yl beta-D-glucopyranoside
-
-
-
-
?
additional information
?
-
-
UGT71K3b shows lower activity towards the substrates, except for morin, when compared with the activity of UGT71K3a
-
-
?
UDP-alpha-D-glucose + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
UDP + 3,5-dihydroxy-4-(2-methylpropanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-2-(2-methylpropanoyl)phenyl beta-D-glucopyranoside
-
the enzyme catalyzes the last step of acylphloroglucinol glucoside biosynthesis
-
-
?
UDP-alpha-D-glucose + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
UDP + 3,5-dihydroxy-4-(2-methylpropanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-2-(2-methylpropanoyl)phenyl beta-D-glucopyranoside
-
phlorisovalerophenone i.e. 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one. The 2-glucoside is the major product. More than 80% of the substrate are converted to the corresponding glucoside
-
-
?
UDP-alpha-D-glucose + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
UDP + 3,5-dihydroxy-2-(3-methylbutanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-4-(3-methylbutanoyl)phenyl beta-D-glucopyranoside
-
the enzyme catalyzes the last step of acylphloroglucinol glucoside biosynthesis
-
-
?
UDP-alpha-D-glucose + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
UDP + 3,5-dihydroxy-2-(3-methylbutanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-4-(3-methylbutanoyl)phenyl beta-D-glucopyranoside
-
phlorisobutyrophenone i.e. 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one. The 2-glucoside is the major product. More than 80% of the substrate are converted to the corresponding glucoside
-
-
?
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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-alpha-D-glucose + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
UDP + 3,5-dihydroxy-4-(2-methylpropanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-2-(2-methylpropanoyl)phenyl beta-D-glucopyranoside
-
the enzyme catalyzes the last step of acylphloroglucinol glucoside biosynthesis
-
-
?
UDP-alpha-D-glucose + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
UDP + 3,5-dihydroxy-2-(3-methylbutanoyl)phenyl beta-D-glucopyranoside + 3,5-dihydroxy-4-(3-methylbutanoyl)phenyl beta-D-glucopyranoside
-
the enzyme catalyzes the last step of acylphloroglucinol glucoside biosynthesis
-
-
?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.406
4-hydroxy-2,5-dimethyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3b
0.9
4-hydroxy-2,5-dimethyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3a
0.213
5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3b
0.397
5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3a
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0552
4-hydroxy-2,5-dimethyl-3(2H)-furanone
pH 7.0, 30°C, UGT71K3a
0.146
4-hydroxy-2,5-dimethyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3b
0.184
5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3a
0.387
5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone
pH 7.0, 30°C, allelic protein UGT71K3b
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
15 - 35
15 - 35
-
15°C: about 50% of maximal activity, 35°C: about 80% of maximal activity, allelic protein GT71K3a
15 - 35
-
15°C: about 50% of maximal activity, 35°C: about 85% of maximal activity, allelic protein GT71K3b
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
suppression of UGT71K3 activity in transient RNAi-silenced fruits leads to a loss of pigmentation and a substantial decrease of the levels of various APG glucosides and an anthocyanin
metabolism
-
the enzyme catalyzes the last step of acylphloroglucinol glucoside biosynthesis
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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). U71K3_FRAAN
478
0
52590
Swiss-Prot
other Location (Reliability: 4)
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
V383A
mutant of UGT71K3b, mutation leads to enhanced 4-hydroxy-2,5-dimethyl-3(2H)-furanone glucosylation activity compared to the wild-type enzyme, 2fold increase in 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone glycosylation activity relative to the wild-type enzyme
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
heterologously expression as GST-Tag-fusion proteins in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
nutrition
improvement of strawberry flavor, down-regulation of UGT71K3 transcript expression in strawberry receptacles led to a significant reduction in the level of 4-hydroxy-2,5-dimethyl-3(2H)-furanone-glucoside and a smaller decline in 4-hydroxy-2,5-dimethyl-3(2H)-furanone-glucoside-malonate compared with the level in control fruits
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Song, C.; Zhao, S.; Hong, X.; Liu, J.; Schulenburg, K.; Schwab, W.
A UDP-glucosyltransferase functions in both acylphloroglucinol glucoside and anthocyanin biosynthesis in strawberry (Fragaria x ananassa)
Plant J.
85
730-742
2016
Fragaria x ananassa
brenda
Song, C.; Hong, X.; Zhao, S.; Liu, J.; Schulenburg, K.; Huang, F.C.; Franz-Oberdorf, K.; Schwab, W.
Glucosylation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone, the key strawberry flavor compound in strawberry fruit
Plant Physiol.
171
139-151
2016
Fragaria x ananassa (A0A387IZV4), Fragaria x ananassa
brenda
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Release 2023.1 (January 2023)
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