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 (C-5) unit between the pyrophos
phate and benzophenone functionalities while 1b contains a geranyl (C-
10) moiety. Compounds 1a and 1b are competitive inhibitors of yeast fa
rnesyl protein transferase with respect to farnesyl pyrophosphate and
have K-I values of 6000 nM and 700 nM. Upon irradiation, [P-32]-1b pre
ferentially labels the beta-subunits of yeast farnesyl protein transfe
rase and human geranylgeranyl protein transferase. (C) 1997 Elsevier S
cience Ltd.