Polyprenyl phosphates play a central role in the biosynthesis of bacterial cell walls. The enzymes that form polyprenyl phosphates utilize farnesyl pyrophosphate as the natural substrate and initiate a series of biosynthetic reactions. As a result prenyl synthases have been investigated as possible therapeutic targets for new antibacterial agents, and the design and synthesis of prenyl synthase inhibitors has attracted considerable interest. We have synthesized a series of bisphosphonate analogs of geranyl and farnesyl pyrophosphates where the terminal isoprene unit was modified to accommodate anthranilate derivatives. The synthesis of these compounds and their in vitro activity against decaprenyl diphosphate synthase (Rv2361c) will be presented.

Bisphosphonate analogs of geranyl and farnesyl pyrophosphate as potential inhibitors of prenyl synthases

240th National Meeting (2010)

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