Issue 4, 2019

Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity

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

Supplementary files

Article information

Article type
Research Article
Submitted
13 Feb 2019
Accepted
08 Mar 2019
First published
13 Mar 2019

Med. Chem. Commun., 2019,10, 554-558

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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