Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers
dc.contributor.author
Boshkow, Johannes
dc.contributor.author
Fischer, Stefan
dc.contributor.author
Bailey, Adrian M.
dc.contributor.author
Wolfrum, Susanne
dc.contributor.author
Carreira, Erick M.
dc.date.accessioned
2017-11-08T11:46:12Z
dc.date.available
2017-10-10T01:55:47Z
dc.date.available
2017-11-08T11:46:12Z
dc.date.issued
2017-10
dc.identifier.issn
2041-6520
dc.identifier.issn
2041-6539
dc.identifier.other
10.1039/c7sc03124f
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/193530
dc.identifier.doi
10.3929/ethz-b-000193530
dc.description.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.
en_US
dc.format
application/pdf
dc.language.iso
en
en_US
dc.publisher
Royal Society of Chemistry
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc/3.0/
dc.title
Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial 3.0 Unported
dc.date.published
2017-08-09
ethz.journal.title
Chemical Science
ethz.journal.volume
8
en_US
ethz.journal.issue
10
en_US
ethz.journal.abbreviated
Chem. Sci.
ethz.pages.start
6904
en_US
ethz.pages.end
6910
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.wos
ethz.publication.place
Cambridge
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03511 - Carreira, Erick M. / Carreira, Erick M.
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03511 - Carreira, Erick M. / Carreira, Erick M.
ethz.date.deposited
2017-10-10T01:56:08Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2017-11-08T11:46:18Z
ethz.rosetta.lastUpdated
2022-03-28T18:00:52Z
ethz.rosetta.versionExported
true
ethz.COinS
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