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Issue 18, 2011
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A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof

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Abstract

Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1′- disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.

Graphical abstract: A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof

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Publication details

The article was received on 18 Apr 2011, accepted on 09 Jun 2011 and first published on 09 Jun 2011


Article type: Paper
DOI: 10.1039/C1OB05619K
Citation: Org. Biomol. Chem., 2011,9, 6278-6283
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    A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof

    M. Adinolfi, D. Capasso, S. Di Gaetano, A. Iadonisi, L. Leone and A. Pastore, Org. Biomol. Chem., 2011, 9, 6278
    DOI: 10.1039/C1OB05619K

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