Journal of Antibiotics 2010-01-01

The first examples of chemical modification of oligomycin A.

Lyudmila N Lysenkova, Konstantin F Turchin, Valery N Danilenko, Alexander M Korolev, Maria N Preobrazhenskaya

Index: J. Antibiot. 63(1) , 17-22, (2010)

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Abstract

The first examples of chemical modification of antibiotic oligomycin A are described. The interaction of oligomycin A with hydroxylamine yielded six-membered nitrone annelated with the antibiotic at the positions 3,4,5,6,7. The reaction with 1-aminopyridinium iodide in pyridine led to pyrazolo[1,5-a]pyridine conjugated with the antibiotic at the positions 2 and 3 (product of addition to the C(2)-C(3) double bond followed by spontaneous oxidation). The structures of the compounds obtained were supported by NMR and mass spectrometry methods including the (15)N-labeling of compounds.