Geranyl thiolodiphosphate (GSPP) is an analog of GPP in which the non-bridging oxygen has been replaced by sulfur resulting in a less-reactive compound. GSPP is turned over by avian farnesyl diphosphate synthase (FPPase) more slowly than FPP and acts as a competitive inhibitor (K_I = 24.8 μM).

Provided as the tris-ammonium salt

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Publications

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1. Phan, R. M. and C. D. Poulter (2001). “Synthesis of (S)-Isoprenoid Thiodiphosphates as Substrates and Inhibitors.” The Journal of Organic Chemistry 66(20): 6705.2. Phan, R. M. and C. D. Poulter (2000). “Synthesis of Geranyl S-Thiolodiphosphate. A New Alternative Substrate/Inhibitor for Prenyltransferases.” Organic Letters 2(15): 2287.3. Kuzuyama, T., J. P. Noel, et al. (2005). “Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products.” Nature 435(7044): 983.4. Koksal, M., W. K. W. Chou, et al. (2012). “Structure of 2-Methylisoborneol Synthase from Streptomyces coelicolor and Implications for the Cyclization of a Noncanonical C-Methylated Monoterpenoid Substrate.” Biochemistry 51(14): 3011.5. Chen, M., et al. (2013). “Mechanistic Insights from the Binding of Substrate and Carbocation Intermediate Analogues to Aristolochene Synthase.” Biochemistry 52(32): 5441-5453.6. Chen, M., et al. (2016). “Probing the Role of Active Site Water in the Sesquiterpene Cyclization Reaction Catalyzed by Aristolochene Synthase.” Biochemistry 55(20): 2864-2874.