Journal article
Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.
- Boshkow J Laboratorium für Organische Chemie , ETH Zürich , HCI H335, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
- Fischer S Laboratorium für Organische Chemie , ETH Zürich , HCI H335, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
- Bailey AM Laboratorium für Organische Chemie , ETH Zürich , HCI H335, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
- Wolfrum S Laboratorium für Organische Chemie , ETH Zürich , HCI H335, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
- Carreira EM Laboratorium für Organische Chemie , ETH Zürich , HCI H335, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
- 2017-11-18
Published in:
- Chemical science. - 2017
English
The syntheses of (+)-16-epi- and (+)-11,15-di-epi-danicalipin A (2 and 3) are reported. The conformations of the parent diols 5 and 6 as well as the corresponding disulfates 2 and 3 were determined on the basis of J-based configuration analysis and supported by calculations. The impact of configuration on membrane permeability in Gram-negative bacteria and mammalian cell lines was assessed as well as cytotoxicity. Although diastereomer 2 showed similar behavior to natural (+)-danicalipin A (1), strikingly, the more flexible C11,C15-epimer 3 had no effect on permeability and proved equally or more toxic towards multiple cell lines.
- Language
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- English
- Open access status
- gold
- Identifiers
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- DOI 10.1039/c7sc03124f
- PMID 29147515
- Persistent URL
- https://sonar.ch/global/documents/185717
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