Information on EC 2.5.1.109 - brevianamide F prenyltransferase (deoxybrevianamide E-forming)

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The expected taxonomic range for this enzyme is: Aspergillus

EC NUMBER
COMMENTARY hide
2.5.1.109
-
RECOMMENDED NAME
GeneOntology No.
brevianamide F prenyltransferase (deoxybrevianamide E-forming)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + brevianamide F = diphosphate + deoxybrevianamide E
show the reaction diagram
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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stephacidin A biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:brevianamide-F tert-dimethylallyl-C-2-transferase
The enzyme from the fungus Aspergilus sp. MF297-2 is specific for brevianamide F [1], while the enzyme from Aspergillus versicolor accepts a broad range of trytophan-containing cyclic dipeptides [2]. Involved in the biosynthetic pathways of several indole alkaloids such as paraherquamides and malbrancheamides.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene cdpC7PT
-
-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
gene ATEG_04218 or cdpC7PT
UniProt
Manually annotated by BRENDA team
gene ATEG_04218 or cdpC7PT
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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 + (R)-benzodiazepinedione
diphosphate + ?
show the reaction diagram
low activity, (R)-benzodiazepinedione consists of a tryptophanyl and an anthranilyl moiety
-
-
?
dimethylallyl diphosphate + (S)-benzodiazepinedione
diphosphate + ?
show the reaction diagram
best substrate, (S)-benzodiazepinedione consists of a tryptophanyl and an anthranilyl moiety
-
-
?
dimethylallyl diphosphate + benzodiazepinedione
diphosphate + ?
show the reaction diagram
best substrate, active only with benzodiazepinedione consisting of a D-tryptophanyl and an anthranilyl moiety, poor activity with the L-Tryp isomer
-
-
?
dimethylallyl diphosphate + brevianamide F
diphosphate + deoxybrevianamide E
show the reaction diagram
dimethylallyl diphosphate + cyclo-D-Trp-D-Ala
diphosphate +
show the reaction diagram
dimethylallyl diphosphate + cyclo-D-Trp-D-Ala
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-D-Pro
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-D-Pro
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-D-Pro
show the reaction diagram
dimethylallyl diphosphate + cyclo-D-Trp-D-Pro
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Ala
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Ala
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Ala
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Ala
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Pro
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Pro
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Pro
show the reaction diagram
low activity
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Pro
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-D-Trp-L-Trp
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-D-Trp-L-Trp
show the reaction diagram
low activity
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Ala
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Ala
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Ala
show the reaction diagram
low activity
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Ala
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Pro
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Ala
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Ala
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Ala
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Ala
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Phe
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Phe
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
show the reaction diagram
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
show the reaction diagram
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
diphosphate + ?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Xaa
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Xaa
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Tyr-L-Tyr
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Tyr-L-Tyr
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-LTrp-L-Phe
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Phe
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
additional information
?
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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
dimethylallyl diphosphate + brevianamide F
diphosphate + deoxybrevianamide E
show the reaction diagram
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
show the reaction diagram
Q0CQ16
attachment of the prenyl moiety to C-7 of the indole ring
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?
dimethylallyl diphosphate + cyclo-L-Trp-Xaa
diphosphate + 7-(3-methylbut-2-enyl)-cyclo-L-Trp-Xaa
show the reaction diagram
-
-
-
-
?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cu2+
5 mM, about 90% loss of activity
Fe2+
5 mM, about 65% loss of activity
Sn2+
5 mM, about 90% loss of activity
Zn2+
5 mM, about 90% loss of activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.204
(S)-benzodiazepinedione
pH 7.5, 37°C
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0.00433 - 0.032
brevianamide F
1.318
cyclo-D-Trp-D-Ala
37°C, pH 7.5; pH 7.5, 37°C
0.709
cyclo-D-Trp-D-Pro
37°C, pH 7.5; pH 7.5, 37°C
0.139 - 1.318
cyclo-D-Trp-L-Ala
2.906
cyclo-D-Trp-L-Pro
37°C, pH 7.5; pH 7.5, 37°C
0.793
cyclo-L-Trp-D-Ala
37°C, pH 7.5; pH 7.5, 37°C
0.082
cyclo-L-Trp-D-Pro
37°C, pH 7.5; pH 7.5, 37°C
1.3
cyclo-L-Trp-Gly
37°C, pH 7.5; pH 7.5, 37°C
0.942
cyclo-L-Trp-L-Ala
37°C, pH 7.5; pH 7.5, 37°C
0.106
cyclo-L-Trp-L-Leu
37°C, pH 7.5; pH 7.5, 37°C
0.094
cyclo-L-Trp-L-Phe
37°C, pH 7.5; pH 7.5, 37°C
0.214
cyclo-L-Trp-L-Tyr
37°C, pH 7.5; pH 7.5, 37°C
1.411
cyclo-L-Tyr-L-Tyr
pH 7.5, 37°C
-
0.00131 - 0.098
dimethylallyl diphosphate
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.125
(S)-benzodiazepinedione
Aspergillus terreus
Q0CQ16
pH 7.5, 37°C
-
0.276 - 0.32
brevianamide F
0.011
cyclo-D-Trp-D-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.095
cyclo-D-Trp-D-Pro
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.003
cyclo-D-Trp-L-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.027
cyclo-D-Trp-L-Pro
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.013
cyclo-L-Trp-D-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.15
cyclo-L-Trp-D-Pro
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.032
cyclo-L-Trp-Gly
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.035
cyclo-L-Trp-L-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.014
cyclo-L-Trp-L-Leu
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.004
cyclo-L-Trp-L-Phe
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.006
cyclo-L-Trp-L-Tyr
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
0.012
cyclo-L-Tyr-L-Tyr
Aspergillus terreus
Q0CQ16
pH 7.5, 37°C
-
0.067 - 0.49
dimethylallyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8.6 - 73
brevianamide F
6395
0.009
cyclo-D-Trp-D-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28950
0.13
cyclo-D-Trp-D-Pro
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28946
0.021
cyclo-D-Trp-L-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28951
0.009
cyclo-D-Trp-L-Pro
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28947
0.017
cyclo-L-Trp-D-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28949
1.8 - 1.83
cyclo-L-Trp-D-Pro
28945
0.025
cyclo-L-Trp-Gly
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
18740
0.037
cyclo-L-Trp-L-Ala
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28948
0.134
cyclo-L-Trp-L-Leu
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28952
0.04
cyclo-L-Trp-L-Phe
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28953
0.027
cyclo-L-Trp-L-Tyr
Aspergillus versicolor
I4AY86
37°C, pH 7.5; pH 7.5, 37°C
28954
4.99 - 320
dimethylallyl diphosphate
157
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 10
pH 5.0: about 50% of maximal activity, pH 10.0: about 70% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 50
20-40: maximal activity, 50°C: about 30% of maximal activity
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
x * 45000, SDS-PAGE
53600
x * 53600, calculated from sequence
62000
recombinant His6-tagged enzyme, gel filtration
292000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli strain M15 by nickel affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene ATEG_04218 or cdpC7PT, cloning from genomic DNA, DNA and amino acid sequence determination and analysis, recombinant expression of His6-tagged enzyme in Escherichia coli strain M15
overexpression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E108D
mutant loses at least 92% of its activity
E108G
mutant loses at least 92% of its activity
R122G
mutant with less than 2% catalytic activity
R122H
mutant with less than 2% catalytic activity
W424G
mutant loses more than 98% of its activity
W424Y
mutant retains about 25% of its activity
E108D
-
mutant loses at least 92% of its activity
-
E108G
-
mutant loses at least 92% of its activity
-
R122G
-
mutant with less than 2% catalytic activity
-
R122H
-
mutant with less than 2% catalytic activity
-
W424Y
-
mutant retains about 25% of its activity
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis