Crystallization (Comment) | Organism |
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crystal structure analysis | Aspergillus fumigatus |
Protein Variants | Comment | Organism |
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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 | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
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dimethylallyl diphosphate + L-tryptophan | Aspergillus fumigatus | C-4 prenylation | diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan | - |
? |
Organism | UniProt | Comment | Textmining |
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Aspergillus fumigatus | Q50EL0 | - |
- |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
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2-pentenyl diphosphate + L-tryptophan | C-5 prenylation | Aspergillus fumigatus | diphosphate + 5-(pent-2-enyl)-L-tryptophan | - |
? | |
benzyl diphosphate + L-tryptophan | C-5 prenylation | Aspergillus fumigatus | diphosphate + 5-benzyl-L-tryptophan | - |
? | |
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 | - |
? | |
dimethylallyl diphosphate + 4-amino-L-Phe | C-3 prenylation | Aspergillus fumigatus | diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-Phe | - |
? | |
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 | - |
? | |
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 | - |
? | |
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 | - |
? | |
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 | - |
? | |
dimethylallyl diphosphate + beta-homo-L-tryptophan | 51.5% of the activity with L-Trp | Aspergillus fumigatus | ? | - |
? | |
dimethylallyl diphosphate + cyclo-L-Trp-Gly | - |
Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly | - |
? | |
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu | - |
Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu | - |
? | |
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro | - |
Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro | - |
? | |
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp | - |
Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp | - |
? | |
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr | - |
Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr | - |
? | |
dimethylallyl diphosphate + D-tryptophan | 9.7% of the activity with L-Trp | Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan | - |
? | |
dimethylallyl diphosphate + DL-indole-3-lactic acid | 10.5% of the activity with L-Trp | Aspergillus fumigatus | ? | - |
? | |
dimethylallyl diphosphate + indole-3-propionic acid | 32.2% of the activity with L-Trp | Aspergillus fumigatus | ? | - |
? | |
dimethylallyl diphosphate + L-abrine | 58.0% of the activity with L-Trp | Aspergillus fumigatus | ? | - |
? | |
dimethylallyl diphosphate + L-tryptophan | best substrate | Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | C-4 prenylation | Aspergillus fumigatus | diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
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 | - |
? | |
methylallyl diphosphate + L-tryptophan | C-4 and C-5 prenylation | Aspergillus fumigatus | diphosphate + 5-(but-2-enyl)-L-tryptophan | - |
? | |
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 | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
FgaPT2 | - |
Aspergillus fumigatus |
tryptophan C4-PT | - |
Aspergillus fumigatus |
General Information | Comment | Organism |
---|---|---|
evolution | the enzyme is part of the DMATS superfamily | Aspergillus fumigatus |