Information on EC 2.5.1.124 - 6-linalyl-2-O,3-dimethylflaviolin synthase

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The expected taxonomic range for this enzyme is: Streptomyces

EC NUMBER
COMMENTARY hide
2.5.1.124
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RECOMMENDED NAME
GeneOntology No.
6-linalyl-2-O,3-dimethylflaviolin synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + 2-O,3-dimethylflaviolin = diphosphate + 6-linalyl-2-O,3-dimethylflaviolin
show the reaction diagram
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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.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + flaviolin
?
show the reaction diagram
geranyl diphosphate + 1,3-dihydroxynaphthalene
?
show the reaction diagram
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
show the reaction diagram
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 6-prenyl-2-methoxy-3-methylflaviolin
show the reaction diagram
geranyl diphosphate + flaviolin
diphosphate + 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,6,7-trihydroxynaphthalene-1,4-dione
show the reaction diagram
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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
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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
show the reaction diagram
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
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 6-prenyl-2-methoxy-3-methylflaviolin
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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addition of 5 mM MgCl2 results in only a 30% increase in activity
additional information
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the reaction proceeds independently of divalent cations
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
0.048 - 0.35
flaviolin
0.059 - 0.098
geranyl diphosphate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00013
1,3-dihydroxynaphthalene
Streptomyces sp.
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.00066
2-O-methyl-3-methylflaviolin
Streptomyces sp.
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
0.00087 - 0.028
flaviolin
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00041
1,3-dihydroxynaphthalene
Streptomyces sp.
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
8477
0.012
2-O-methyl-3-methylflaviolin
Streptomyces sp.
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pH 7.5, 30°C, cosubstrate geranyl diphosphate
8970
0.0025 - 0.58
flaviolin
4425
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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