Synthesis and Biological Evaluation of a Valinomycin Analog Bearing a Pentafluorophenyl Active Ester Moiety.

Lucia D'Accolti, Nunzio Denora, Gianluigi La Piana, Domenico Marzulli, Zuzanna S Siwy, Caterina Fusco, Cosimo Annese

The Journal of organic chemistry 2015 Dec 18

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A 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.

Citation

Lucia D'Accolti, Nunzio Denora, Gianluigi La Piana, Domenico Marzulli, Zuzanna S Siwy, Caterina Fusco, Cosimo Annese. Synthesis and Biological Evaluation of a Valinomycin Analog Bearing a Pentafluorophenyl Active Ester Moiety. The Journal of organic chemistry. 2015 Dec 18;80(24):12646-50