Abstract
The goal of this study was to determine the substrate specificity of Homo sapiens geranylgeranyl diphosphate synthase (GGPPase) for analogs of isopentenyl diphosphate (IPP) to facilitate the application to organic synthesis techniques to the study of prenyl chain elongation enzymes. For this purpose, we used the IPP analogs 2a–d, which contain different alkyl side-chains at the 3-position, as substrates of the condensation reaction with the allylic substrate geranyl diphosphate (GPP) that is catalyzed by GGPPase. GGPPase catalyzed the reaction of GPP with 3-desmethylisopentenyl diphosphate (but-3-enyl diphosphate) to yield 3-desmethylfarnesyl diphosphate (12.1%), as well as the reaction of GPP with 3-ethylbut-3-enyl diphosphate or 3-propylbut-3-enyl diphosphate to yield 3-ethylfarnesyl diphosphate (46.9%) or 3-propylfarnesyl diphosphate (22.6%), respectively. However, a reaction product was not detected when 3-butylbut-3-enyl diphosphate was used as substrate.
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