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geranyl diphosphate:2-O-methyl-3-methylflaviolin geranyltransferase 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
The enzyme is involved in furaquinocin biosynthesis in the bacterium Streptomyces sp. KO-3988. It catalyses the transfer of a geranyl group to 2-O,3-dimethylflaviolin to yield 7-O-geranyl-2-O,3-dimethylflaviolin and 6-linalyl-2-O,3-dimethylflaviolin (cf. EC 2.5.1.124, 6-linalyl-2-O,3-dimethylflaviolin synthase) in a 1:10 ratio.
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dimethylallyl diphosphate + flaviolin
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Substrates: -
Products: -
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geranyl diphosphate + 1,3-dihydroxynaphthalene
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Substrates: -
Products: -
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geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
geranyl diphosphate + flaviolin
diphosphate + 3-(3,7-dimethylocta-1,6-dien-3-yl)-2,5,7-trihydroxynaphthalene-1,4-dione
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Substrates: -
Products: -
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geranyl diphosphate + flaviolin
diphosphate + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,5,7-trihydroxynaphthalene-1,4-dione
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Substrates: i.e. 2,5,7-trihydroxynaphthalene-1,4-dione. The kcat/Km of the prenylation of flaviolin is significantly higher than that of the prenylation of the natural substrate 2-O-methyl-3-methylflaviolin
Products: -
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geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
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Substrates: the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin. It catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 1:10 ratio
Products: -
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geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
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Substrates: the enzyme catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 1:10 ratio
Products: -
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geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
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Substrates: the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin. It catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 1:10 ratio
Products: -
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geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
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Substrates: the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin. It catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 1:10 ratio
Products: -
?
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
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Substrates: the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin. It catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 1:10 ratio
Products: -
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0.32
1,3-dihydroxynaphthalene
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.054
2-O-methyl-3-methylflaviolin
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.72
dimethylallyl diphosphate
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pH 7.5, 30°C, cosubstrate: flaviolin
0.059 - 0.098
geranyl diphosphate
0.048
flaviolin
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.35
flaviolin
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pH 7.5, 30°C, cosubstrate dimethylallyl diphosphate
0.059
geranyl diphosphate
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pH 7.5, 30°C, cosubstrate: flaviolin
0.063
geranyl diphosphate
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pH 7.5, 30°C, cosubstrate: 1,3-dihydroxynaphthalene
0.098
geranyl diphosphate
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pH 7.5, 30°C, cosubstrate: 2-methoxy-3-methylflaviolin
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0.00013
1,3-dihydroxynaphthalene
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.00066
2-O-methyl-3-methylflaviolin
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.00087 - 0.028
flaviolin
0.00087
flaviolin
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pH 7.5, 30°C, cosubstrate dimethylallyl diphosphate
0.028
flaviolin
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
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0.00041
1,3-dihydroxynaphthalene
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.012
2-O-methyl-3-methylflaviolin
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.0025
flaviolin
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pH 7.5, 30°C, cosubstrate dimethylallyl diphosphate
0.58
flaviolin
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
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malfunction
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Streptomyces albus transformant (pWHMFur2_del7) harboring the furaquinocin biosynthetic gene cluster lacking the fur7 gene does not produce furaquinocin but synthesizes the novel intermediate 2-O-methyl-3-methyl-flaviolin. When 6-prenyl-2-methoxy-3-methyl-flaviolin is added to the culture medium of Streptromyces albus/pWHM-Fur2_del7, furaquinocin production is restored
malfunction
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Streptomyces albus transformant (pWHMFur2_del7) harboring the furaquinocin biosynthetic gene cluster lacking the fur7 gene does not produce furaquinocin but synthesizes the novel intermediate 2-O-methyl-3-methyl-flaviolin. When 6-prenyl-2-methoxy-3-methyl-flaviolin is added to the culture medium of Streptromyces albus/pWHM-Fur2_del7, furaquinocin production is restored
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physiological function
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the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin
physiological function
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the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin
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