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Literature summary extracted from

  • Schwarzer, D.; Gritsch, P.; Gaich, T.
    Mimicking dimethylallyltryptophan synthase: experimental evidence for a biosynthetic cope rearrangement process (2012), Angew. Chem. Int. Ed. Engl., 51, 11514-11516.
    View publication on PubMed

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.34 dimethylallyl diphosphate + L-tryptophan Claviceps purpurea
-
 diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.34 Claviceps purpurea
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
2.5.1.34 dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan enzyme-catalyzed sigmatropic process in the C-4 prenylation of indole alkaloids, an initial reverse prenylation of tryptophan at C-3 with dimethylallyl diphosphate, the subsequent Cope rearrangement shifts the prenyl moiety to the C-4 position and re-aromatization gives dimethylallyltryptophan, reaction mechanism,overview Claviceps purpurea
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.34 dimethylallyl diphosphate + L-tryptophan
-
 Claviceps purpurea diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
 ?
2.5.1.34 additional information normal prenylation at C-4 of tryptophan is catalyzed by dimethylallyltryptophan synthase, the enzyme forms a C-C bond at the least nucleophilic position (C-4) of the indole core, instead of the highly nucleophilic positions C-2 and C-3 Claviceps purpurea ?
-
 ?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.34 22
-
 assay at room temperature Claviceps purpurea

General Information

EC Number General Information Comment Organism
2.5.1.34 metabolism 4-DMATS catalyzes the first step in the biosynthesis of ergot alkaloids Claviceps purpurea