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Information on EC 2.5.1.124 - 6-linalyl-2-O,3-dimethylflaviolin synthase
for references in articles please use BRENDA:EC2.5.1.124
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EC Tree 2 Transferases
2.5 Transferring alkyl or aryl groups, other than methyl groups
2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
2.5.1.124 6-linalyl-2-O,3-dimethylflaviolin synthase
IUBMB Comments
The enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin D in the bacterium Streptomyces sp. KO-3988. It catalyses the transfer of a geranyl group to 2-O,3-dimethylflaviolin to yield 6-linalyl-2-O,3-dimethylflaviolin and 7-O-geranyl-2-O,3-dimethylflaviolin (cf. EC 2.5.1.125, 7-geranyloxy-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione synthase) in a 10:1 ratio.
The expected taxonomic range for this enzyme is: unclassified Streptomyces
Reaction Schemes
showSynonyms
Fur7, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Fur7
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + 2-O,3-dimethylflaviolin = diphosphate + 6-linalyl-2-O,3-dimethylflaviolin
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SYSTEMATIC NAME
IUBMB Comments
geranyl diphosphate:2-O-methyl-3-methylflaviolin geranyltransferase (6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione-forming)
The enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin D in the bacterium Streptomyces sp. KO-3988. It catalyses the transfer of a geranyl group to 2-O,3-dimethylflaviolin to yield 6-linalyl-2-O,3-dimethylflaviolin and 7-O-geranyl-2-O,3-dimethylflaviolin (cf. EC 2.5.1.125, 7-geranyloxy-5-hydroxy-2-methoxy-3-methylnaphthalene-1,4-dione synthase) in a 10:1 ratio.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + 1,3-dihydroxynaphthalene
?
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
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
diphosphate + 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
geranyl diphosphate + flaviolin
diphosphate + 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,6,7-trihydroxynaphthalene-1,4-dione
geranyl diphosphate + flaviolin
diphosphate + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,5,7-trihydroxynaphthalene-1,4-dione
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
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
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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 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
Products: -
Products: -
?
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
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
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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 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
Products: -
Products: -
?
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
-
Substrates: 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
Products: -
Products: -
?
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
diphosphate + 6-(3,7-dimethylocta-1,6-dien-3-yl)-5,7-dihydroxy-2-methoxy-3-methylnaphthalene-1,4-dione
-
Substrates: 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
Products: -
Products: -
?
geranyl diphosphate + flaviolin
diphosphate + 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,6,7-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: -
Products: -
?
geranyl diphosphate + flaviolin
diphosphate + 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,6,7-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: -
Products: -
?
geranyl diphosphate + flaviolin
diphosphate + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,5,7-trihydroxynaphthalene-1,4-dione
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + flaviolin
diphosphate + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,5,7-trihydroxynaphthalene-1,4-dione
-
Substrates: -
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
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
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
-
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 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
Products: -
Products: -
?
geranyl diphosphate + 2-O-methyl-3-methylflaviolin
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
-
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 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
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
the reaction proceeds independently of divalent cations
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.32
1,3-dihydroxynaphthalene
-
pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.054
2-O-methyl-3-methylflaviolin
-
pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.063
geranyl diphosphate
-
pH 7.5, 30°C, cosubstrate: 1,3-dihydroxynaphthalene
0.098
geranyl diphosphate
-
pH 7.5, 30°C, cosubstrate: 2-methoxy-3-methylflaviolin
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00013
1,3-dihydroxynaphthalene
-
pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.00066
2-O-methyl-3-methylflaviolin
-
pH 7.5, 30°C, cosubstrate geranyl diphosphate
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00041
1,3-dihydroxynaphthalene
-
pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.012
2-O-methyl-3-methylflaviolin
-
pH 7.5, 30°C, cosubstrate geranyl diphosphate
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
physiological function
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
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
-
physiological function
-
the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin
physiological function
-
the enzyme is involved in biosynthesis of the polyketide-isoprenoid furaquinocin
-
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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). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kumano, T.; Tomita, T.; Nishiyama, M.; Kuzuyama, T.
Functional characterization of the promiscuous prenyltransferase responsible for furaquinocin biosynthesis: identification of a physiological polyketide substrate and its prenylated reaction products
J. Biol. Chem.
285
39663-39671
2010
Streptomyces sp., Streptomyces sp. KO-3988
brenda
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