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Literature summary for 2.5.1.106 extracted from

  • Pan, L.L.; Yang, Y.; Merz, K.M.
    Origin of product selectivity in a prenyl transfer reaction from the same intermediate: exploration of multiple FtmPT1-catalyzed prenyl transfer pathways (2014), Biochemistry, 53, 6126-6138.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
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Aspergillus fumigatus

Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus Q4WAW7
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Aspergillus fumigatus ATCC MYA-4609 Q4WAW7
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + brevianamide F
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Aspergillus fumigatus diphosphate + (2S,3aR,8aR)-3a-(2-methylbut-3-en-2-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid product of mutant G115T, no product of wild-type ?
dimethylallyl diphosphate + brevianamide F
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Aspergillus fumigatus ATCC MYA-4609 diphosphate + (2S,3aR,8aR)-3a-(2-methylbut-3-en-2-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid product of mutant G115T, no product of wild-type ?
additional information the C5-C8 and C2-C9 reaction channels have very similar activation parameters for the prenylation step. Hence, the final proton ransfer/cyclization step is the product-determining step, with the deprotonation of the C5-C8 intermediate being nearly without activation (0.5 kcal/mol), while the deprotonation process for the C2-C9 pathway has a substantial barrier (higher than the C5-C8 and C2-C9 intermediate states) of 16.8 kcal/mol, resulting in the exclusive formation of the wild-type product tryprostatin B. The diphosphate anion leaving group is stabilized throughout by Arg113, Lys201, Tyr205, Gln380, Lys294, Tyr450, and nine crystal water molecules in the active site Aspergillus fumigatus ?
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?
additional information the C5-C8 and C2-C9 reaction channels have very similar activation parameters for the prenylation step. Hence, the final proton ransfer/cyclization step is the product-determining step, with the deprotonation of the C5-C8 intermediate being nearly without activation (0.5 kcal/mol), while the deprotonation process for the C2-C9 pathway has a substantial barrier (higher than the C5-C8 and C2-C9 intermediate states) of 16.8 kcal/mol, resulting in the exclusive formation of the wild-type product tryprostatin B. The diphosphate anion leaving group is stabilized throughout by Arg113, Lys201, Tyr205, Gln380, Lys294, Tyr450, and nine crystal water molecules in the active site Aspergillus fumigatus ATCC MYA-4609 ?
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Synonyms

Synonyms Comment Organism
FtmPT1
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Aspergillus fumigatus