Farnesyl and geranylgeranyl pyrophosphate analogs incorporating benzoylbenzyl ethers: Synthesis and inhibition of yeast protein farnesyltransferase

Igor Gaon, Tammy C. Turek, Mark D. Distefano

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30 Scopus citations

Abstract

The syntheses of two photoactive analogs (1a and 1b) of farnesyl pyrophosphate that incorporate stable ether-linked benzophenones are described. Compounds 1a and 1b were prepared from geraniol in 17% overall yield. Both in and 1b are competitive inhibitors of yeast protein farnesyltransferase with respect to farnesyl pyrophosphate and have K1 values of 45 nM and 49 nM. Upon photolysis for twelve hours, 1a and 1b both inactivate the enzyme by 40%. Copyright (C) 1996 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)8833-8836
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number49
DOIs
StatePublished - Dec 2 1996

Bibliographical note

Funding Information:
Acknowledgments: This researchw as supported by funds from the American Cancer Society (BE-222, IN-13-33-47, and JFRA-584). We thank C. D. Poulter for providing E. cofi DHSu/pGP114 and Mr. S. E. Murray for mass spectral analyses.

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