Information on EC 2.5.1.70 - naringenin 8-dimethylallyltransferase

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The expected taxonomic range for this enzyme is: Sophora flavescens

EC NUMBER
COMMENTARY hide
2.5.1.70
-
RECOMMENDED NAME
GeneOntology No.
naringenin 8-dimethylallyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + (-)-(2S)-naringenin = diphosphate + sophoraflavanone B
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sophoraflavanone G biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:naringenin 8-dimethylallyltransferase
Requires Mg2+. This membrane-bound protein is located in the plastids [2]. In addition to naringenin, the enzyme can prenylate several other flavanones at the C-8 position, but more slowly. Along with EC 1.14.13.103 (8-dimethylallylnaringenin 2'-hydroxylase) and EC 2.5.1.71 (leachianone G 2′′-dimethylallyltransferase), this enzyme forms part of the sophoraflavanone-G-biosynthesis pathway.
CAS REGISTRY NUMBER
COMMENTARY hide
158130-09-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3,3-dimethylallyl diphosphate + (2S)-liquiritigenin
diphosphate + isobavachin
show the reaction diagram
3,3-dimethylallyl diphosphate + (2S)-naringenin
8-dimethylallylnaringenin + diphosphate
show the reaction diagram
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
show the reaction diagram
3,3-dimethylallyl diphosphate + 2'-hydroxynaringenin
diphosphate + leachianone G
show the reaction diagram
-
with 2'-hydroxynaringenin, i.e. (S)-2',4',5,7-tetrahydroxy-flavanone, the enzyme shows 3% of the activity with naringenin
-
-
?
3,3-dimethylallyl diphosphate + apigenin
diphosphate + ?
show the reaction diagram
-
-
-
?
3,3-dimethylallyl diphosphate + hesperetin
diphosphate + (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
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i.e. 5,7,3'-trihydroxy-4'-methoxyflavanone
-
-
?
3,3-dimethylallyl diphosphate + hesperetin
diphosphate + ?
show the reaction diagram
52% of the activity with naringenin
-
-
?
3,3-dimethylallyl diphosphate + kaempferol
diphosphate + ?
show the reaction diagram
-
-
-
?
3,3-dimethylallyl diphosphate + liquiritigenin
diphosphate + ?
show the reaction diagram
102% of the activity with naringenin
-
-
?
3,3-dimethylallyl diphosphate + quercetin
diphosphate + ?
show the reaction diagram
-
-
-
?
3,3-dimethylallyl diphosphate + taxifolin
diphosphate + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
i.e. 3,5,7,3',4'-pentahydroxyflavanone
-
-
?
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
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
6% of the activity with Mg2+
Co2+
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5% of the activity with Mg2+
Cu2+
-
1% of the activity with Mg2+
Mn2+
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32% of the activity with Mg2+
Zn2+
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2% of the activity with Mg2+
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.036 - 0.05
(2S)-naringenin
0.025 - 0.12
3,3-dimethylallyl diphosphate
0.055
naringenin
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.001
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microsomes
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 10
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
gene expression is strictly limited to the root bark
Manually annotated by BRENDA team
additional information
no detectable expression in aerial tissues
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
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subcellular localization of the enzymes involved in the biosynthetic route from naringenin to sophoraflavanone G, overview
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Manually annotated by BRENDA team
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by microsome preparation
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae
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expression in Arabidopsis thaliana
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
construction of chimeric enzymes between narigenin 8-dimethylallyltransferase and isoflavone-specific prenyltransferase G6DT responsible for the prenylation of the genistein at the 6-position, by recombination of amino acid sequences within the loop domains. Chimera SfG2N possesses purely narigenin 8-dimethylallyltransferase activity despite the absence of the N-terminal sequence derived from narigenin 8-dimethylallyltransferase, 243 amino acids. Chimera SfG3N possesses only isoflavone-specific prenyltransferase G6DT activity, although its 33% of the C-terminus is from narigenin 8-dimethylallyltransferase polypeptide. Neither chimeric enzyme can catalyze the prenylation reaction for other types of flavonoid such as kaempferol, apigenin, naringenin chalcone