Information on EC 2.1.1.261 - 4-dimethylallyltryptophan N-methyltransferase

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The expected taxonomic range for this enzyme is: Aspergillus fumigatus

EC NUMBER
COMMENTARY hide
2.1.1.261
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RECOMMENDED NAME
GeneOntology No.
4-dimethylallyltryptophan N-methyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + 4-dimethylallyl-L-tryptophan = S-adenosyl-L-homocysteine + 4-dimethylallyl-L-abrine
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chanoclavine I aldehyde biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:4-(3-methylbut-2-enyl)-L-tryptophan N-methyltransferase
The enzyme catalyses a step in the pathway leading to biosynthesis of ergot alkaloids in certain fungi.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene fgaMT, ATCC 13073
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 4-dimethylallyl-L-tryptophan
S-adenosyl-L-homocysteine + 4-dimethylallyl-L-abrine
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
S-adenosyl-L-methionine + 4-dimethylallyl-L-tryptophan
S-adenosyl-L-homocysteine + 4-dimethylallyl-L-abrine
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
13% inhibition at 5 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.12
4-dimethylallyl-L-tryptophan
pH 7.5, 37C, recombinant enzyme
2.4
S-adenosyl-L-methionine
pH 7.5, 37C, recombinant enzyme
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2
4-dimethylallyl-L-tryptophan
Aspergillus fumigatus
B6D5I7
pH 7.5, 37C, recombinant enzyme
2
S-adenosyl-L-methionine
Aspergillus fumigatus
B6D5I7
pH 7.5, 37C, recombinant enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
38100
2 * 40000, recombinant His6-tagged enzyme, SDS-PAGE, x * 39200, about, His6-tagged enzyme, sequence calculation, x * 38100, about, non-tagged enzyme, sequence calculation
39200
2 * 40000, recombinant His6-tagged enzyme, SDS-PAGE, x * 39200, about, His6-tagged enzyme, sequence calculation, x * 38100, about, non-tagged enzyme, sequence calculation
40000
2 * 40000, recombinant His6-tagged enzyme, SDS-PAGE, x * 39200, about, His6-tagged enzyme, sequence calculation, x * 38100, about, non-tagged enzyme, sequence calculation
75000
recombinant His6-tagged enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant soluble His6-tagged enzyme in Escherichia coli strain XL-1 blue MRF- by nickel affinity chromatography and gel filtration to apparent homogeneity
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene easF, a fragment of genomic DNA containing dmaW, easF, easE, and easC is amplified from the human-pathogenic, ergot alkaloid-producing fungus Aspergillus fumigatus and transformed into Aspergillus nidulans strain FGSC A767, a model fungus that does not contain any of the ergot alkaloid synthesis genes. Transformed Aspergillus nidulans strains produces chanoclavine-I and an earlier pathway intermediate
gene fgaMT, DNA and amino acid sequence determination and analysis, overexpression of the soluble His6-tagged enzyme in Escherichia coli strain XL-1 blue MRF-
recombinant heterologous enzyme expression in Aspergillus nidulans
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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an engineered strain named Aspergillus nidulans WFC, expressing ergot alkaloid synthesis genes dmaW, easF, and easC, produces the established intermediate N-methyl-4-dimethylallyltryptophan, as well as an ergot alkaloid, that is characterized as ergotryptamine, it differs from N-methyl-4-dimethylallyltryptophan by the loss of the carboxyl group, addition of a hydroxyl group, and shift in position of a carbon-carbon double bond, by mass spectrometry, labeling, and NMR. Feeding studies with Aspergillus mutants do not show ergotryptamine turnover, suggesting it is a pathway byproduct as opposed to an authentic intermediate
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
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ergot alkaloid pathway reconstruction in Aspergillus nidulans is an approach used to better understand the biosynthesis of these mycotoxins