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Literature summary for 2.5.1.124 extracted from
- Functional characterization of the promiscuous prenyltransferase responsible for furaquinocin biosynthesis: identification of a physiological polyketide substrate and its prenylated reaction products (2010), J. Biol. Chem., 285, 39663-39671.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expression in Escherichia coli | Streptomyces sp. |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.048 | - |
flaviolin | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. |  |
| 0.054 | - |
2-O-methyl-3-methylflaviolin | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
| 0.059 | - |
geranyl diphosphate | pH 7.5, 30°C, cosubstrate: flaviolin | Streptomyces sp. | |
| 0.063 | - |
geranyl diphosphate | pH 7.5, 30°C, cosubstrate: 1,3-dihydroxynaphthalene | Streptomyces sp. | |
| 0.098 | - |
geranyl diphosphate | pH 7.5, 30°C, cosubstrate: 2-methoxy-3-methylflaviolin | Streptomyces sp. | |
| 0.32 | - |
1,3-dihydroxynaphthalene | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
| 0.35 | - |
flaviolin | pH 7.5, 30°C, cosubstrate dimethylallyl diphosphate | Streptomyces sp. | |
| 0.72 | - |
dimethylallyl diphosphate | pH 7.5, 30°C, cosubstrate: flaviolin | Streptomyces sp. | |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Mg2+ | addition of 5 mM MgCl2 results in only a 30% increase in activity | Streptomyces sp. | |
| additional information | the reaction proceeds independently of divalent cations | Streptomyces sp. |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| geranyl diphosphate + 2-O-methyl-3-methylflaviolin | Streptomyces sp. | 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 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 10:1 ratio | diphosphate + (E)-7-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione + 6-prenyl-2-methoxy-3-methylflaviolin | - |
? | |
| geranyl diphosphate + 2-O-methyl-3-methylflaviolin | Streptomyces sp. KO-3988 | 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 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 10:1 ratio | diphosphate + (E)-7-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione + 6-prenyl-2-methoxy-3-methylflaviolin | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Streptomyces sp. | - |
- |
- |
| Streptomyces sp. KO-3988 | - |
- |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
- |
Streptomyces sp. |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| dimethylallyl diphosphate + flaviolin | - |
Streptomyces sp. | ? | - |
? | |
| dimethylallyl diphosphate + flaviolin | - |
Streptomyces sp. KO-3988 | ? | - |
? | |
| geranyl diphosphate + 1,3-dihydroxynaphthalene | - |
Streptomyces sp. | ? | - |
? | |
| geranyl diphosphate + 1,3-dihydroxynaphthalene | - |
Streptomyces sp. KO-3988 | ? | - |
? | |
| geranyl diphosphate + 2-O-methyl-3-methylflaviolin | 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 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 10:1 ratio | Streptomyces sp. | diphosphate + (E)-7-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione + 6-prenyl-2-methoxy-3-methylflaviolin | - |
? | |
| geranyl diphosphate + 2-O-methyl-3-methylflaviolin | 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 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 10:1 ratio | Streptomyces sp. KO-3988 | diphosphate + (E)-7-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione + 6-prenyl-2-methoxy-3-methylflaviolin | - |
? | |
| geranyl diphosphate + 2-O-methyl-3-methylflaviolin | the enzyme catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 10:1 ratio | Streptomyces sp. | diphosphate + 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione | - |
? | |
| geranyl diphosphate + 2-O-methyl-3-methylflaviolin | the enzyme catalyses the transfer of a geranyl group to 2-O-methyl-3-methyl-flaviolin to yield 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione and 7-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione in a 10:1 ratio | Streptomyces sp. KO-3988 | diphosphate + 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione | - |
? | |
| geranyl diphosphate + flaviolin | - |
Streptomyces sp. | diphosphate + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,5,7-trihydroxynaphthalene-1,4-dione | - |
? | |
| geranyl diphosphate + flaviolin | - |
Streptomyces sp. KO-3988 | diphosphate + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,5,7-trihydroxynaphthalene-1,4-dione | - |
? | |
| geranyl diphosphate + flaviolin | 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 | Streptomyces sp. | diphosphate + 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,6,7-trihydroxynaphthalene-1,4-dione | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| Fur7 | - |
Streptomyces sp. |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 30 | - |
assay at | Streptomyces sp. |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.00013 | - |
1,3-dihydroxynaphthalene | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
| 0.00066 | - |
2-O-methyl-3-methylflaviolin | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
| 0.00087 | - |
flaviolin | pH 7.5, 30°C, cosubstrate dimethylallyl diphosphate | Streptomyces sp. | |
| 0.028 | - |
flaviolin | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.5 | - |
assay at | Streptomyces sp. |
General Information
| General Information | Comment | Organism |
|---|---|---|
| malfunction | 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 | Streptomyces sp. |
| physiological function | the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin | Streptomyces sp. |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.00041 | - |
1,3-dihydroxynaphthalene | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
| 0.0025 | - |
flaviolin | pH 7.5, 30°C, cosubstrate dimethylallyl diphosphate | Streptomyces sp. | |
| 0.012 | - |
2-O-methyl-3-methylflaviolin | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
| 0.58 | - |
flaviolin | pH 7.5, 30°C, cosubstrate geranyl diphosphate | Streptomyces sp. | |
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