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Verification of oligomycin A structure: synthesis and biological evaluation of 33-dehydrooligomycin Aстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 16 мая 2018 г.
- Авторы: Lysenkova Lyudmila N., Saveljev Oleg Y., Grammatikova Natalya E., Tsvetkov Vladimir B., Bekker Olga B., Danilenko Valery N., Dezhenkova Lyubov G., Bykov Eugene E., Omelchuk Olga A., Korolev Alexander M., Shchekotikhin Andrey E.
- Журнал: Journal of Antibiotics
- Том: 70
- Год издания: 2017
- Издательство: Japan Antibiotics Research Association/Nihon Koseibusshitsu Gakujutsu Kyogikai
- Местоположение издательства: Japan
- Первая страница: 871
- Последняя страница: 877
- DOI: 10.1038/ja.2017.48
- Аннотация: Although, the structure of oligomycin A (1) was confirmed by spectroscopic and chemical evaluations, some crystallographic data cast doubt on the originally adopted structure of the side 2-hydroxypropyl moiety of this antibiotic. It was suggested that the side chain of the oligomycin is enol-related (2-hydroxy-1-propenyl). To clarify this matter we synthesized and evaluated 33-dehydrooligomycin A (2) prepared by the Kornblum oxidation of 33-O-mesyloligomycin A (3) by dimethyl sulfoxide. NMR data for 33-dehydrooligomycin (2) and results of quantum chemical calculations have shown that this derivative exists in the keto rather than in the enol tautomer 2a. The in vitro antimicrobial activity of 2 was approximately two times weaker in comparison with oligomycin A against Streptomyces fradiae ATCC-19609 and reference Candida spp. strains and similar activity against certain filamentous fungi. The docking binding estimate of 2 with FOF1ATP synthase showed a slight decrease in binding affinity for 2 when compared with oligomycin A; that correlated with its activity against S. fradiae ATCC 19609 that is supersensitive to oligomycin A. The in vitro antiproliferative activities of 2 are also discussed.
- Добавил в систему: Польшаков Владимир Иванович