Details

Autor(en) / Beteiligte

• Boshkow, J
• Fischer, S
• Bailey, A M
• Wolfrum, S
• Carreira, E M

Titel

Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers

Ist Teil von

• Chemical science (Cambridge), 2017-10, Vol.8 (10), p.6904-6910

Ort / Verlag

England

Erscheinungsjahr

2017

Link zum Volltext

Quelle

Elektronische Zeitschriftenbibliothek (Open access)

Beschreibungen/Notizen

• The syntheses of (+)-16- - and (+)-11,15-di- -danicalipin A ( and ) are reported. The conformations of the parent diols and as well as the corresponding disulfates and were determined on the basis of -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 showed similar behavior to natural (+)-danicalipin A ( ), strikingly, the more flexible C11,C15-epimer had no effect on permeability and proved equally or more toxic towards multiple cell lines.