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Issue 10, 2017
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Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers

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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

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Publication details

The article was received on 17 Jul 2017, accepted on 07 Aug 2017 and first published on 09 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC03124F
Citation: Chem. Sci., 2017,8, 6904-6910
  • Open access: Creative Commons BY-NC license
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    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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