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
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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
stephacidin A biosynthesis
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Biosynthesis of antibiotics
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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
-
UniProt
Manually annotated by BRENDA team
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 + 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-Pro
diphosphate +
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-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-Gly
diphosphate +
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-Phe
diphosphate +
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
diphosphate +
show the reaction diagram
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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
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
enzyme activity is independent of divalent cation, although addition of 5 mM Mg2+, Ca2+ or Mn2+ slightly enhances catalysis (about 100-120%)
Mg2+
enzyme activity is independent of divalent cation, although addition of 5 mM Mg2+, Ca2+ or Mn2+ slightly enhances catalysis (about 100-120%)
Mn2+
enzyme activity is independent of divalent cation, although addition of 5 mM Mg2+, Ca2+ or Mn2+ slightly enhances catalysis (about 100-120%)
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
0.00433 - 0.032
brevianamide F
1.318
cyclo-D-Trp-D-Ala
pH 7.5, 37C
0.709
cyclo-D-Trp-D-Pro
pH 7.5, 37C
0.139
cyclo-D-Trp-L-Ala
pH 7.5, 37C
2.906
cyclo-D-Trp-L-Pro
pH 7.5, 37C
0.793
cyclo-L-Trp-D-Ala
pH 7.5, 37C
0.082
cyclo-L-Trp-D-Pro
pH 7.5, 37C
1.3
cyclo-L-Trp-Gly
pH 7.5, 37C
0.942
cyclo-L-Trp-L-Ala
pH 7.5, 37C
0.106
cyclo-L-Trp-L-Leu
pH 7.5, 37C
0.094
cyclo-L-Trp-L-Phe
pH 7.5, 37C
0.214
cyclo-L-Trp-L-Tyr
pH 7.5, 37C
0.00131 - 0.098
dimethylallyl diphosphate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.276 - 0.32
brevianamide F
0.011
cyclo-D-Trp-D-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.095
cyclo-D-Trp-D-Pro
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.003
cyclo-D-Trp-L-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.027
cyclo-D-Trp-L-Pro
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.013
cyclo-L-Trp-D-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.15
cyclo-L-Trp-D-Pro
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.032
cyclo-L-Trp-Gly
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.035
cyclo-L-Trp-L-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.014
cyclo-L-Trp-L-Leu
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.004
cyclo-L-Trp-L-Phe
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.006
cyclo-L-Trp-L-Tyr
Aspergillus versicolor
I4AY86
pH 7.5, 37C
0.42 - 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
pH 7.5, 37C
28950
0.13
cyclo-D-Trp-D-Pro
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28946
0.021
cyclo-D-Trp-L-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28951
0.009
cyclo-D-Trp-L-Pro
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28947
0.017
cyclo-L-Trp-D-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28949
1.8
cyclo-L-Trp-D-Pro
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28945
0.025
cyclo-L-Trp-Gly
Aspergillus versicolor
I4AY86
pH 7.5, 37C
18740
0.037
cyclo-L-Trp-L-Ala
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28948
0.134
cyclo-L-Trp-L-Leu
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28952
0.04
cyclo-L-Trp-L-Phe
Aspergillus versicolor
I4AY86
pH 7.5, 37C
28953
0.027
cyclo-L-Trp-L-Tyr
Aspergillus versicolor
I4AY86
pH 7.5, 37C
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, 50C: about 30% of maximal activity
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
292000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
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mutant loses at least 92% of its activity
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E108G
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mutant loses at least 92% of its activity
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R122G
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mutant with less than 2% catalytic activity
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R122H
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mutant with less than 2% catalytic activity
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W424Y
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mutant retains about 25% of its activity
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