title: Synthesis and Biological Evaluation of a Valinomycin Analog Bearing a Pentafluorophenyl Active Ester Moiety.
abstract: 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.
authors.affiliation: CNR - Istituto di Chimica dei Composti Organometallici (ICCOM) , Bari section, via Orabona 4, 70126 Bari, Italy.
authors.forename: Lucia
authors.initials: L
authors.lastname: D'Accolti
authors.forename: Nunzio
authors.initials: N
authors.lastname: Denora
authors.forename: Gianluigi
authors.initials: G
authors.lastname: La Piana
authors.affiliation: CNR - Istituto di Biomembrane e Bioenergetica (IBBE) , via Amendola 165/A, 70126 Bari, Italy.
authors.forename: Domenico
authors.initials: D
authors.lastname: Marzulli
authors.affiliation: School of Physical Sciences, University of California , Irvine, California 92697, United States.
authors.forename: Zuzanna S
authors.initials: ZS
authors.lastname: Siwy
authors.affiliation: CNR - Istituto di Chimica dei Composti Organometallici (ICCOM) , Bari section, via Orabona 4, 70126 Bari, Italy.
authors.forename: Caterina
authors.initials: C
authors.lastname: Fusco
authors.affiliation: CNR - Istituto di Chimica dei Composti Organometallici (ICCOM) , Bari section, via Orabona 4, 70126 Bari, Italy.
authors.forename: Cosimo
authors.initials: C
authors.lastname: Annese
mesh_terms: D004952:Esters; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007476:Ionophores / Q000737:chemistry; D015394:Molecular Structure; D011188:Potassium / Q000737:chemistry; D014634:Valinomycin / Q000138:chemical synthesis* / Q000737:chemistry; D005466:Fluorocarbons
chemical_list: D004952:Esters; D005998:Glycine; D006845:Hydrocarbons, Fluorinated; D007476:Ionophores; D011188:Potassium; D014634:Valinomycin; C000607873:pentafluorophenyl N-carbonyl glycinate; D005466:Fluorocarbons