Synthesis and evaluation of benzophenone-based photoaffinity labeling analogs of prenyl pyrophosphates containing stable amide linkages

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

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

The syntheses of two photoactive prenyl pyrophosphate analogs (1a and 1b) that incorporate stable amide-linked benzophenones are described. Compound 1a contains a single isoprene (C5) unit between the phyophosphate and benzophenone functionalities while 1b contains a geranyl (C10) moiety. Compounds 1a and 1b are competitive inhibitors of yeast farnesyl protein transferase with respect to farnesyl pyrophosphate and have K(I) values of 6000 nM. and 700 nM. Upon irradiation [32P]-1b preferentially labels the β-subunits of yeast farnesyl protein transferase and human geranylgeranyl protein transferase.

Original languageEnglish (US)
Pages (from-to)2125-2130
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume7
Issue number16
DOIs
StatePublished - Aug 19 1997

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