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Issue 4, 2019
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Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity

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Abstract

We describe a straightforward synthesis of the apramycin biosynthetic precursor saccharocin from apramycin by regioselective partial azidation followed by stereoretentive oxidative deamination. Saccharocin was found to exhibit excellent selectivity for inhibition of the bacterial ribosome over the eukaryotic ribosomes indicating that its presence as a minor impurity in apramycin itself should not be problematic in the development of the latter as a clinical candidate.

Graphical abstract: Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity

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Publication details

The article was received on 13 Feb 2019, accepted on 08 Mar 2019 and first published on 13 Mar 2019


Article type: Research Article
DOI: 10.1039/C9MD00093C
Citation: Med. Chem. Commun., 2019,10, 554-558

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    Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity

    V. A. Sarpe, M. G. Pirrone, K. Haldimann, S. N. Hobbie, A. Vasella and D. Crich, Med. Chem. Commun., 2019, 10, 554
    DOI: 10.1039/C9MD00093C

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