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Literature summary for 2.5.1.34 extracted from

  • Fan, A.; Winkelblech, J.; Li, S.M.
    Impacts and perspectives of prenyltransferases of the DMATS superfamily for use in biotechnology (2015), Appl. Microbiol. Biotechnol., 99, 7399-7415.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
crystal structure analysis Aspergillus fumigatus

Protein Variants

Protein Variants Comment Organism
K174A site.directed mutagenesis, the mutant FgaPT2 converts tryptophan mainly to a reversely C3-prenylated derivative, while the regularly C4-prenylated tryptophan is detected as a minor product Aspergillus fumigatus
additional information molecular modeling-guided site-directed mutagenesis of FgaPT2. FgaPT2 is displayed on the surface of Escherichia coli cells by using autodisplay technique for chemoenzymatic synthesis. Indole-3-propionic acid and L-beta-homotryptophan are tested with the FgaPT2 whole cell biocatalyst, and conversion yields of 30 and 13% are obtained, respectively. Its catalytic efficiency is much higher than that of the purified FgaPT2 in a 24-h assay toward indole-3-propionic acid, overview Aspergillus fumigatus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus C-4 prenylation diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
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Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus Q50EL0
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-pentenyl diphosphate + L-tryptophan C-5 prenylation Aspergillus fumigatus diphosphate + 5-(pent-2-enyl)-L-tryptophan
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benzyl diphosphate + L-tryptophan C-5 prenylation Aspergillus fumigatus diphosphate + 5-benzyl-L-tryptophan
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dimethylallyl diphosphate + 11-methyl-DL-tryptophan 1.6% of the activity with L-Trp Aspergillus fumigatus diphosphate + 11-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
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dimethylallyl diphosphate + 4-amino-L-Phe C-3 prenylation Aspergillus fumigatus diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-Phe
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dimethylallyl diphosphate + 5-hydroxy-L-tryptophan 21.0% of the activity with L-Trp Aspergillus fumigatus diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
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dimethylallyl diphosphate + 5-methyl-DL-tryptophan 8.1% of the activity with L-Trp Aspergillus fumigatus diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
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dimethylallyl diphosphate + 6-methyl-DL-tryptophan 15.2% of the activity with L-Trp Aspergillus fumigatus diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
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dimethylallyl diphosphate + 7-methyl-DL-tryptophan 16.3% of the activity with L-Trp Aspergillus fumigatus diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
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dimethylallyl diphosphate + beta-homo-L-tryptophan 51.5% of the activity with L-Trp Aspergillus fumigatus ?
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dimethylallyl diphosphate + cyclo-L-Trp-Gly
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Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
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dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
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Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
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dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
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Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
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dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
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Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
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dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
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Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
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dimethylallyl diphosphate + D-tryptophan 9.7% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
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dimethylallyl diphosphate + DL-indole-3-lactic acid 10.5% of the activity with L-Trp Aspergillus fumigatus ?
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dimethylallyl diphosphate + indole-3-propionic acid 32.2% of the activity with L-Trp Aspergillus fumigatus ?
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dimethylallyl diphosphate + L-abrine 58.0% of the activity with L-Trp Aspergillus fumigatus ?
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dimethylallyl diphosphate + L-tryptophan best substrate Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
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dimethylallyl diphosphate + L-tryptophan C-4 prenylation Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
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dimethylallyl diphosphate + L-Tyr C-3 prenylation Aspergillus fumigatus diphosphate + 3-(3-methylbut-2-enyl)-L-Tyr 3-dimethylallyl-L-tyrosine ?
methylallyl diphosphate + L-tryptophan C-4 and C-5 prenylation Aspergillus fumigatus diphosphate + 4-(but-2-enyl)-L-tryptophan
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methylallyl diphosphate + L-tryptophan C-4 and C-5 prenylation Aspergillus fumigatus diphosphate + 5-(but-2-enyl)-L-tryptophan
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?
additional information no or poor activity with N-acetyl-DL-Trp, 5-bromo-DL-Trp, 4-methyl-DL-Trp, 1-methyl-DL-Trp, and 6-fluoro-DL-Trp. The tryptophan prenyltransferase FgaPT2 takes L-tyrosine and 4-amino-L-phenylalanine as substrates as well and produces the unique C3-prenylated tyrosine or 4-amino-L-phenylalanine, cf. EC 2.5.1.122, no activity with D-Tyr, 3-fluoro-DL-Tyr, 3-iodo-L-Tyr, and alpha-methyl-L-Tyr. FgaPT2 also catalyzes regiospecific prenylations of indolocarbazoles at the para-position of the indole N-atom. In the presence of methylallyl diphosphate, MAPP, a mixture of C4- and C5-alkylated tryptophan is observed for FgaPT2 reaction,t FgaPT2 even uses the more space-demanding substrate benzyl diphosphate as donor and produces regiospecifically C5-benzylated tryptophan and eight derivatives thereof, overview Aspergillus fumigatus ?
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Synonyms

Synonyms Comment Organism
FgaPT2
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Aspergillus fumigatus
tryptophan C4-PT
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Aspergillus fumigatus

General Information

General Information Comment Organism
evolution the enzyme is part of the DMATS superfamily Aspergillus fumigatus