Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity.

ID: ALA4480383

Journal: Medchemcomm

Title: Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity.

Authors: Sarpe VA, Pirrone MG, Haldimann K, Hobbie SN, Vasella A, Crich D.

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.

CiteXplore: 31057735

DOI: 10.1039/C9MD00093C

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