Issue 10, 2017

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Jul 2017
Accepted
07 Aug 2017
First published
09 Aug 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 6904-6910

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

J. Boshkow, S. Fischer, A. M. Bailey, S. Wolfrum and E. M. Carreira, Chem. Sci., 2017, 8, 6904 DOI: 10.1039/C7SC03124F

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