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The first examples of chemical modification of oligomycin A. The Journal of antibiotics [J Antibiot (Tokyo)] Journal article

 
Lysenkova LN, Turchin KF, Danilenko VN, Korolev AM, Preobrazhenskaya MN 
The first examples of chemical modification of oligomycin A. [JOURNAL ARTICLE]
J Antibiot (Tokyo) 2009 Nov 13.


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.The Journal of Antibiotics advance online publication, 13 November 2009; doi:10.1038/ja.2009.112.



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