Cloned (Comment) | Organism |
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- |
Aspergillus fumigatus |
Crystallization (Comment) | Organism |
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crystal structures of unliganded enzyme FtmPT1 to 2.5 A resolution as well as of a ternary complex of FtmPT1 bound to brevianamide F and an analogue of its isoprenoid substrate dimethylallyl diphosphate. FtmPT1 assumes a rare alpha/beta-barrel fold, consisting of 10 circularly arranged -strands surrounded by alpha-helices. Catalysis is performed in a hydrophobic reaction chamber at the center of the barrel | Aspergillus fumigatus |
Protein Variants | Comment | Organism |
---|---|---|
E102Q | mutation reduces the production of tryprostatin B to undetectable amounts | Aspergillus fumigatus |
G115A | no change in prenylation position of product | Aspergillus fumigatus |
G115I | complete loss of activity | Aspergillus fumigatus |
G115L | formation of tryprostatin B is abolished, formation of a new product occurs | Aspergillus fumigatus |
G115T | 0.4% of wild-type activity in formation of trytrostatin B. Mutant catalyzes the formation of a different product that carries a reverse prenyl moiety at the C-3 of the indole nucleus | Aspergillus fumigatus |
H279F | 70% of wild-type activity | Aspergillus fumigatus |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Aspergillus fumigatus | Q4WAW7 | - |
- |
Aspergillus fumigatus Af293 | Q4WAW7 | - |
- |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
dimethylallyl diphosphate + brevianamide F | - |
Aspergillus fumigatus | diphosphate + tryprostatin B | mutant G115T catalyzes the formation of a different product that carries a reverse prenyl moiety at the C-3 of the indole nucleus | ? | |
dimethylallyl diphosphate + brevianamide F | - |
Aspergillus fumigatus Af293 | diphosphate + tryprostatin B | mutant G115T catalyzes the formation of a different product that carries a reverse prenyl moiety at the C-3 of the indole nucleus | ? | |
additional information | the reaction is most likely initiated by hydrolysis of the phosphoric acid ester bond to form the dimethylallylic cation and a diphosphate group. The resulting carbocation would be stabilized from two sides by cation-pi interactions with aromatic ring systems, one from the substrate brevianamide F and one from the side chain of Y382. The stabilized cation can then undergo a nucleophilic attack from an aromatic nucleus such as that of the indole. The reactivity of the indole is likely enhanced by a hydrogen bond from its N-1 nitrogen to the side chain carboxylate of E102 | Aspergillus fumigatus | ? | - |
? | |
additional information | the reaction is most likely initiated by hydrolysis of the phosphoric acid ester bond to form the dimethylallylic cation and a diphosphate group. The resulting carbocation would be stabilized from two sides by cation-pi interactions with aromatic ring systems, one from the substrate brevianamide F and one from the side chain of Y382. The stabilized cation can then undergo a nucleophilic attack from an aromatic nucleus such as that of the indole. The reactivity of the indole is likely enhanced by a hydrogen bond from its N-1 nitrogen to the side chain carboxylate of E102 | Aspergillus fumigatus Af293 | ? | - |
? |