The first examples of chemical modification of oligomycin A.
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.
Lysenkova
Lyudmila N
LN
Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russian Federation.
Turchin
Konstantin F
KF
Danilenko
Valery N
VN
Korolev
Alexander M
AM
Preobrazhenskaya
Maria N
MN
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000378:metabolism*; D019811:Hydroxylamine / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009840:Oligomycins / Q000737:chemistry* / Q000378:metabolism*; D011725:Pyridines / Q000378:metabolism
D000900:Anti-Bacterial Agents; D009840:Oligomycins; D011725:Pyridines; C031004:oligomycin A; D019811:Hydroxylamine; C023666:pyridine