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3,3-dimethylallyl diphosphate + (2S)-liquiritigenin
diphosphate + isobavachin
3,3-dimethylallyl diphosphate + (2S)-naringenin
8-dimethylallylnaringenin + diphosphate
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
3,3-dimethylallyl diphosphate + 2'-hydroxynaringenin
diphosphate + leachianone G
-
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 + ?
-
-
-
?
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
-
i.e. 5,7,3'-trihydroxy-4'-methoxyflavanone
-
-
?
3,3-dimethylallyl diphosphate + hesperetin
diphosphate + ?
52% of the activity with naringenin
-
-
?
3,3-dimethylallyl diphosphate + kaempferol
diphosphate + ?
-
-
-
?
3,3-dimethylallyl diphosphate + liquiritigenin
diphosphate + ?
102% of the activity with naringenin
-
-
?
3,3-dimethylallyl diphosphate + quercetin
diphosphate + ?
-
-
-
?
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
-
i.e. 3,5,7,3',4'-pentahydroxyflavanone
-
-
?
dimethylallyl diphosphate + (-)-(2S)-naringenin
diphosphate + sophoraflavanone B
-
-
-
?
additional information
?
-
3,3-dimethylallyl diphosphate + (2S)-liquiritigenin
diphosphate + isobavachin
-
-
-
?
3,3-dimethylallyl diphosphate + (2S)-liquiritigenin
diphosphate + isobavachin
-
i.e. 4',7-dihydroxyflavanone
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
8-dimethylallylnaringenin + diphosphate
-
-
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
8-dimethylallylnaringenin + diphosphate
-
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
-
-
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
-
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
-
two possible pathways leading to sophoraflavanone G, overview
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
-
best substrate, the enzyme is enantiospecific for (2S)-naringenin, i.e. (S)-4',5,7-trihydroxy-flavanone, and utilizes 3,3-dimethylallyl diphosphate as sole prenyl donor
-
-
?
3,3-dimethylallyl diphosphate + (2S)-naringenin
diphosphate + sophoraflavanone B
-
i.e. (S)-4',5,7-trihydroxy-flavanone
-
-
?
additional information
?
-
-
substrate specificity, formation of 8-dimethylallyl-, 8-lavandulyl- and 6-dimethylallylflavanones, overview
-
-
?
additional information
?
-
no substrate: geranyl diphosphate, farnesyl diphosphate, geranylgeranyl diphosphate, and phytyl diphosphate
-
-
?
additional information
?
-
-
no substrate: geranyl diphosphate, farnesyl diphosphate, geranylgeranyl diphosphate, and phytyl diphosphate
-
-
?
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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
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
additional information
production of prenylated flavonoids in Solanum lycopersicum as a host plant by means of metabolic engineering through recombinant overexpression of both the naringenin 8-dimethylallyltransferase (N8DT) gene, encoding a prenyltransferase from Sophora flavescens, and the chalcone isomerase (CHI) gene from Nicotiana tabacum cv. Samsun-NN, in transgenic tomato lines. Production of 8-dimethylallyl naringenin in the double transformants, while the production level is lower than N8DT single transformants. Tomato fruits overexpressing both N8DT and CHI genes accumulate high levels of rutin compared with wild-type tomato
additional information
production of prenylated flavonoids in Solanum lycopersicum as a host plant by means of metabolic engineering through recombinant overexpression of both the naringenin 8-dimethylallyltransferase (N8DT) gene, encoding a prenyltransferase from Sophora flavescens, and the chalcone isomerase (CHI) gene from Nicotiana tabacum cv. Samsun-NN, in transgenic tomato lines. Production of 8-dimethylallyl naringenin in the double transformants, while the production level is lower than N8DT single transformants. Tomato fruits overexpressing both N8DT and CHI genes accumulate high levels of rutin compared with wild-type tomato
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Yamamoto, H.; Senda, M.; Inoue, K.
Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures
Phytochemistry
54
649-655
2000
Sophora flavescens
brenda
Zhao, P.; Inoue, K.; Kouno, I.; Yamamoto, H.
Characterization of leachianone G 2''-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme for the formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures
Plant Physiol.
133
1306-1313
2003
Sophora flavescens
brenda
Sasaki, K.; Mito, K.; Ohara, K.; Yamamoto, H.; Yazaki, K.
Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens
Plant Physiol.
146
1075-1084
2008
Sophora flavescens (B1B3P3), Sophora flavescens
brenda
Sasaki, K.; Tsurumaru, Y.; Yazaki, K.
Prenylation of flavonoids by biotransformation of yeast expressing plant membrane-bound prenyltransferase SfN8DT-1
Biosci. Biotechnol. Biochem.
73
759-761
2009
Sophora flavescens
brenda
Sasaki, K.; Tsurumaru, Y.; Yamamoto, H.; Yazaki, K.
Molecular characterization of a membrane-bound prenyltransferase specific for isoflavone from Sophora flavescens
J. Biol. Chem.
286
24125-24134
2011
Sophora flavescens (F8WPJ0), Sophora flavescens
brenda
Kawasaki, T.; Koeduka, T.; Sugiyama, A.; Sasaki, K.; Linley, P.; Shitan, N.; Kumano, T.; Yamamoto, H.; Ezura, H.; Kuzuyama, T.; Yazaki, K.
Metabolic engineering of flavonoids with prenyltransferase and chalcone isomerase genes in tomato fruits
Plant Biotechnol.
31
567-571
2014
Sophora flavescens (B1B3P3), Sophora flavescens (B1B5P4)
-
brenda