jo5b02219_si_001.pdf (1.25 MB)
Synthesis and Biological Evaluation of a Valinomycin Analog Bearing a Pentafluorophenyl Active Ester Moiety
journal contribution
posted on 2015-12-18, 00:00 authored by Lucia D’Accolti, Nunzio Denora, Gianluigi La Piana, Domenico Marzulli, Zuzanna
S. Siwy, Caterina Fusco, Cosimo AnneseA valuable analog of the K+-ionophore valinomycin (1), bearing a pentafluorophenyl
ester moiety, has been obtained
by selective reaction between the tertiary hydroxyl moiety of analog 2 (available from valinomycin hydroxylation) and the isocyanate
group of pentafluorophenyl N-carbonyl glycinate (3) catalyzed by bis(N,N-dimethylformamide)dichlorodioxomolybdenum(VI).
LC-HRMS studies show that analog 4 undergoes easy derivatization
under mild conditions by reaction with OH- and NH2-containing
compounds. Mitochondrial depolarization assays suggest that 4 acts as a K+-ionophore, provided that the glycine
carboxyl group is appropriately masked.