EC Number |
Reaction |
Reference |
---|
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
- |
- |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
ability of dimethylallyltryptophan synthase to prenylate at five different sites on the indole nucleus, with normal and reverse prenylation at one of the sites, is consistent with a dissociative electrophilic alkylation of the indole ring, where orientation of the substrates within the active site and substituent electronic effects determine the position and type of prenylation |
722461 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
catalytic reaction mechanism, overview |
722461 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
Cope mechanism for the reaction catalyzed by DMAT synthase, overview |
722452 |
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 |
721293 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
random sequential mechanism |
-, 637463 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
reaction mechanism and substrate specificity, overview |
723326 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
sequential mechanism |
-, 637459 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
SN1-like mechanism involving a discrete carbocation intermediate involving initial ion pair formation followed by a reverse prenylation at the nucleophilic C-3 position, detailed overview |
726466 |
2.5.1.34 | dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan |
stereochemistry, direct attack of dimethylallyl diphosphate on C-4 of the indole |
637460 |