Elsevier

Tetrahedron Letters

Volume 37, Issue 28, 8 July 1996, Pages 4845-4848
Tetrahedron Letters

Analogs of farnesyl pyrophosphate incorporating internal benzoylbenzoate esters: Synthesis, inhibition kinetics and photoinactivation of yeast protein farnesyltransferase

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Abstract

The syntheses of two analogs (1a and 1b) of farnesyl pyrophosphate incorporating photoactive benzoylbenzoate esters are described. Both 1a and 1b are competitive inhibitors of yeast protein farnesyltransferase with respect to farnesyl pyrophosphate and have Ki values of 3300 nM and 880 nM, respectively. Upon photolysis for two hours, 1a and 1b inactivate the enzyme by 46% and 11%, respectively. These compounds should be useful for a variety of studies of protein prenyltransferases.

Compounds 1a and 1b are competitive inhibitors of yeast protein farnesyltransferase and inactivate the enzyme upon photolysis.

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