Synthesis of geranyl S-thiolodiphosphate. A new alternative substrate/inhibitor for prenyltransferases

[GRAPHICS] The tris(tetra-n-butylammonium) salt of thiopyrophosphate 5 was prepared fr om trimethyl phosphate in four steps. Treatment of geranyl bromide with 5 g ave an 80% yield of geranyl S-thiolodiphosphate (6), Thiolodiphosphate 6 is substantially less reactive than geranyl diphosphate (7) in the prenyl tra nsfer reaction catalyzed by farnesyl diphosphate synthase and is a good inh ibitor of the enzyme.