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

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.