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Stereospecific synthesis and biological evaluation of farnesyl diphosphate isomers
Y Shao1, J T Eummer, R A Gibbs
1Department of Pharmaceutical Sciences, College of Pharmacy and Allied Health Professions, Wayne State University, Detroit, Michigan 48202, USA. rag@wizard.pharm.wayne.edu
Organic Letters
|May 24, 2000
Abstract:
[formula: see text] A unified, stereospecific synthetic route to the three geometric isomers of (E,E)-farnesyl diphosphate (E,E-FPP) (1, 2, and 3) has been developed. The key feature of this synthesis is the ability to control the stereochemistry of triflation of the beta-ketoester 10 to give either 11 or 14. Preliminary evaluation of these compounds with protein-farnesyl transferase indicates that 1 and 2 are surprisingly effective substrates; however, Z,Z-FPP (3) is a poor substrate and a sub-micromolar inhibitor.