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dimethylallyl diphosphate + (2Z)-3-(1H-indol-3-yl)prop-2-enenitrile
diphosphate + (2E)-3-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]prop-2-enenitrile + (2E)-3-[2-(3-methylbut-2-en-1-yl)-3H-indol-3-yl]prop-2-enenitrile
dimethylallyl diphosphate + 1,6-dihydroxynaphthalene
diphosphate + 1-O-dimethylallyl-1,6-dihydroxynaphthalene
dimethylallyl diphosphate + 2,7-dihydroxynaphthalene
diphosphate + 1-dimethylallyl-2,7-dihydroxynaphthalene
dimethylallyl diphosphate + 3'-hydroxydaidzein
?
2% conversion
-
-
?
dimethylallyl diphosphate + 4'-hydroxy-6-methoxyflavone
?
1% conversion
-
-
?
dimethylallyl diphosphate + 4'-hydroxy-7-methoxyflavone
?
2% conversion
-
-
?
dimethylallyl diphosphate + 4'-hydroxy-7-methoxyflavone
diphosphate + 2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-methoxy-4H-chromen-4-one + 7-methoxy-2-[4-[(3-methylbut-2-en-1-yl)oxy]phenyl]-4H-chromen-4-one
2% conversion
-
-
?
dimethylallyl diphosphate + 4-coumarate
diphosphate + 4-O-dimethylallylcoumarate
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
dimethylallyl diphosphate + 7,4'-dihydroxyflavone
?
4% conversion
-
-
?
dimethylallyl diphosphate + apigenin
diphosphate + 3'-C-dimethylallyl apigenin
7.6% yield
-
-
?
dimethylallyl diphosphate + caffeate
diphosphate + 3-O,4-O-bis-(dimethylallyl)caffeate
20% yield
-
-
?
dimethylallyl diphosphate + caffeate
diphosphate + 3-O-(dimethylallyl)caffeate
17.3% yield
-
-
?
dimethylallyl diphosphate + caffeate
diphosphate + 4-O-(dimethylallyl)caffeate
26.1% yield
-
-
?
dimethylallyl diphosphate + coumestrol
?
1% conversion
-
-
?
dimethylallyl diphosphate + daidzein
?
less than 1% conversion
-
-
?
dimethylallyl diphosphate + equol
?
8% conversion
-
-
?
dimethylallyl diphosphate + equol
diphosphate + 3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-chromen-7-ol + 3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-7-ol
2% conversion
-
-
?
dimethylallyl diphosphate + genistein
?
less than 1% conversion
-
-
?
dimethylallyl diphosphate + hapalindole U
diphosphate + ambiguine H
dimethylallyl diphosphate + luteolin
?
3% conversion
-
-
?
dimethylallyl diphosphate + menadione hydroquinol
diphosphate + vitamin MK1
dimethylallyl diphosphate + naringenin
diphosphate + 3'-C-dimethylallyl naringenin
87.2% yield
-
-
?
dimethylallyl diphosphate + naringenin
diphosphate + 4'-O-dimethylallyl naringenin
11.1% yield
-
-
?
dimethylallyl diphosphate + resveratrol
?
2% conversion
-
-
?
dimethylallyl diphosphate + resveratrol
diphosphate + 3'-dimethylallyl resveratrol
12.3% yield
-
-
?
geranyl diphosphate + (2Z)-3-(1H-indol-3-yl)prop-2-enenitrile
diphosphate + (2Z)-3-(2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl)prop-2-enenitrile + (2E)-3-(2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3H-indol-3-yl)prop-2-enenitrile
additional information
?
-
dimethylallyl diphosphate + (2Z)-3-(1H-indol-3-yl)prop-2-enenitrile
diphosphate + (2E)-3-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]prop-2-enenitrile + (2E)-3-[2-(3-methylbut-2-en-1-yl)-3H-indol-3-yl]prop-2-enenitrile
dimethylallyl diphosphate is preferred over geranyl diphosphate
-
-
?
dimethylallyl diphosphate + (2Z)-3-(1H-indol-3-yl)prop-2-enenitrile
diphosphate + (2E)-3-[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]prop-2-enenitrile + (2E)-3-[2-(3-methylbut-2-en-1-yl)-3H-indol-3-yl]prop-2-enenitrile
dimethylallyl diphosphate is preferred over geranyl diphosphate
-
-
?
dimethylallyl diphosphate + 1,6-dihydroxynaphthalene
diphosphate + 1-O-dimethylallyl-1,6-dihydroxynaphthalene
49.8% yield
-
-
?
dimethylallyl diphosphate + 1,6-dihydroxynaphthalene
diphosphate + 1-O-dimethylallyl-1,6-dihydroxynaphthalene
49.8% yield
-
-
?
dimethylallyl diphosphate + 2,7-dihydroxynaphthalene
diphosphate + 1-dimethylallyl-2,7-dihydroxynaphthalene
31% yield
-
-
?
dimethylallyl diphosphate + 2,7-dihydroxynaphthalene
diphosphate + 1-dimethylallyl-2,7-dihydroxynaphthalene
31% yield
-
-
?
dimethylallyl diphosphate + 4-coumarate
diphosphate + 4-O-dimethylallylcoumarate
16.8% yield
-
-
?
dimethylallyl diphosphate + 4-coumarate
diphosphate + 4-O-dimethylallylcoumarate
34.4% yield
-
-
?
dimethylallyl diphosphate + 4-coumarate
diphosphate + 4-O-dimethylallylcoumarate
16.8% yield
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
-
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
-
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
-
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
-
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
involved in the synthesis of the prenylated hydroxybenzoate moiety of the antibiotic clorobiocin, specifically catalyzing the attachment of a dimethylallyl moiety to 4-hydroxyphenylpyruvate
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
the enzyme is involved in the biosynthesis of the 3-dimethylallyl-4-hydroxyphenylpyruvate moiety of the aminocoumarin antibiotic clorobiocin
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
the enzyme is specific for 4-hydroxyphenylpyruvate. CloQ does not accept prephenic acid, 4-hydroxybenzoate or 4-hydroxybenzaldehyde or as substrate. When dimethylallyl diphosphate is replaced with isopentenyl diphosphate or geranyl diphosphate, no product formation is observed
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
84% conversion
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
the enzyme is involved in the biosynthesis of the 3-dimethylallyl-4-hydroxyphenylpyruvate moiety of the aminocoumarin antibiotic clorobiocin
-
-
?
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate
diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
the enzyme is specific for 4-hydroxyphenylpyruvate. CloQ does not accept prephenic acid, 4-hydroxybenzoate or 4-hydroxybenzaldehyde or as substrate. When dimethylallyl diphosphate is replaced with isopentenyl diphosphate or geranyl diphosphate, no product formation is observed
-
-
?
dimethylallyl diphosphate + hapalindole U
diphosphate + ambiguine H
-
-
-
?
dimethylallyl diphosphate + hapalindole U
diphosphate + ambiguine H
-
-
-
?
dimethylallyl diphosphate + menadione hydroquinol
diphosphate + vitamin MK1
-
-
-
?
dimethylallyl diphosphate + menadione hydroquinol
diphosphate + vitamin MK1
-
-
-
?
geranyl diphosphate + (2Z)-3-(1H-indol-3-yl)prop-2-enenitrile
diphosphate + (2Z)-3-(2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl)prop-2-enenitrile + (2E)-3-(2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3H-indol-3-yl)prop-2-enenitrile
dimethylallyl diphosphate is preferred over geranyl diphosphate
-
-
?
geranyl diphosphate + (2Z)-3-(1H-indol-3-yl)prop-2-enenitrile
diphosphate + (2Z)-3-(2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl)prop-2-enenitrile + (2E)-3-(2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3H-indol-3-yl)prop-2-enenitrile
dimethylallyl diphosphate is preferred over geranyl diphosphate
-
-
?
additional information
?
-
no activity with olivetol, less than 5% yield with genistein, daidzein and 1,3-dihydroxynaphthalene
-
-
?
additional information
?
-
no activity with olivetol, less than 5% yield with genistein, daidzein and 1,3-dihydroxynaphthalene
-
-
?
additional information
?
-
the enzyme shows no activity with isoflavone and glycitein
-
-
-
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Keller, S.; Pojer, F.; Heide, L.; Lawson, D.M.
Crystallization and preliminary X-ray analysis of the aromatic prenyltransferase CloQ from the clorobiocin biosynthetic cluster of Streptomyces roseochromogenes
Acta Crystallogr. Sect. F
62
1153-1155
2006
Streptomyces roseochromogenus subsp. oscitans (Q8GHB2)
brenda
Freitag, A.; Galm, U.; Li, S.M.; Heide, L.
New aminocoumarin antibiotics from a cloQ-defective mutant of the clorobiocin producer Streptomyces roseochromogenes DS12.976
J. Antibiot.
57
205-209
2004
Streptomyces roseochromogenus subsp. oscitans (Q8GHB2)
brenda
Ozaki, T.; Mishima, S.; Nishiyama, M.; Kuzuyama, T.
NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids
J. Antibiot.
62
385-392
2009
Streptomyces niveus (Q9L9F1), Streptomyces niveus 16259 (Q9L9F1)
brenda
Metzger, U.; Keller, S.; Stevenson, C.E.; Heide, L.; Lawson, D.M.
Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway
J. Mol. Biol.
404
611-626
2010
Streptomyces roseochromogenus subsp. oscitans (Q8GHB2)
brenda
Pojer, F.; Wemakor, E.; Kammerer, B.; Chen, H.; Walsh, C.T.; Li, S.M.; Heide, L.
CloQ, a prenyltransferase involved in clorobiocin biosynthesis
Proc. Natl. Acad. Sci. USA
100
2316-2321
2003
Streptomyces roseochromogenus subsp. oscitans (Q8GHB2), Streptomyces roseochromogenus subsp. oscitans DS 12.976 (Q8GHB2)
brenda
Bayse, C.A.; Merz, K.M.
Mechanistic insights into Mg2+-independent prenylation by CloQ from classical molecular mechanics and hybrid quantum mechanics/molecular mechanics molecular dynamics simulations
Biochemistry
53
5034-5041
2014
Streptomyces roseochromogenus subsp. oscitans (Q8GHB2)
brenda
Wang, J.; Chen, C.C.; Yang, Y.; Liu, W.; Ko, T.P.; Shang, N.; Hu, X.; Xie, Y.; Huang, J.W.; Zhang, Y.; Guo, R.T.
Structural insight into a novel indole prenyltransferase in hapalindole-type alkaloid biosynthesis
Biochem. Biophys. Res. Commun.
495
1782-1788
2018
Fischerella ambigua (A0A1J0AKI6), Fischerella ambigua UTEX 1903 (A0A1J0AKI6)
brenda
Ni, W.; Zheng, Z.; Liu, H.; Wang, P.; Wang, H.; Sun, X.; Yang, Q.; Fang, Z.; Tang, H.; Zhao, G.
Combining mutagenesis on Glu281 of prenyltransferase NovQ and metabolic engineering strategies for the increased prenylated activity towards menadione
Appl. Microbiol. Biotechnol.
104
4371-4382
2020
Streptomyces niveus (Q9L9F1), Streptomyces niveus CPCC 240348 (Q9L9F1)
brenda
Ni, W.; Liu, H.; Wang, P.; Wang, L.; Sun, X.; Wang, H.; Zhao, G.; Zheng, Z.
Evaluation of multiple fused partners on enhancing soluble level of prenyltransferase NovQ in Escherichia coli
Bioprocess Biosyst. Eng.
42
465-474
2019
Streptomyces niveus (Q9L9F1), Streptomyces niveus CPCC 240348 (Q9L9F1)
brenda
Araya-Cloutier, C.; Martens, B.; Schaftenaar, G.; Leipoldt, F.; Gruppen, H.; Vincken, J.
Structural basis for non-genuine phenolic acceptor substrate specificity of Streptomyces roseochromogenes prenyltransferase CloQ from the ABBA/PT-barrel superfamily
PLoS ONE
12
e0174665
2017
Streptomyces roseochromogenus subsp. oscitans (Q8GHB2)
brenda
Wu, X.; Li, Z.; Liu, H.; Wang, P.; Wang, L.; Fang, X.; Sun, X.; Ni, W.; Yang, Q.; Zheng, Z.; Zhao, G.
Synthesis of vitamin K2 by isopentenyl transferase NovA in Pichia pastoris Gpn12
Sheng Wu Gong Cheng Xue Bao
34
140-148
2018
Streptomyces niveus
brenda