The first examples of chemical modification of oligomycin A

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 pyrazolo1,5-apyridine conjugated with the antibiotic at the positions 2 and 3 (product of addition to the C2-C3 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. © 2010 Japan Antibiotics Research Association.