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

ABSTRACT: 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.

SUBMITTER: Boshkow J 

PROVIDER: S-EPMC5632803 | biostudies-other | 2017 Oct

REPOSITORIES: biostudies-other

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

Boshkow J J   Fischer S S   Bailey A M AM   Wolfrum S S   Carreira E M EM  

Chemical science 20170809 10

The syntheses of (+)-16-<i>epi</i>- and (+)-11,15-di-<i>epi</i>-danicalipin A (<b>2</b> and <b>3</b>) are reported. The conformations of the parent diols <b>5</b> and <b>6</b> as well as the corresponding disulfates <b>2</b> and <b>3</b> were determined on the basis of <i>J</i>-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 diastereom  ...[more]