2. Academic Validation
  3. Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity

Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity

  • Medchemcomm. 2019 Mar 13;10(4):554-558. doi: 10.1039/c9md00093c.
Vikram A Sarpe 1,  Michael G Pirrone 1,  Klara Haldimann 2,  Sven N Hobbie 2,  Andrea Vasella 3,  David Crich 1
Affiliations

Affiliations

  • 1 Department of Chemistry , Wayne State University , 5101 Cass Avenue , Detroit , MI 48202 , USA . Email: vasarpe@gmail.com ; Email: dcrich@chem.wayne.edu.
  • 2 Institut für Medizinische Mikrobiologie , Universität Zürich , Gloriastrasse 30 , 8006 Zürich , Switzerland.
  • 3 Laboratorium für Organische Chemie , ETH Zürich , Vladimir-Prelog-Weg 1-5/10 , 8093 Zürich , Switzerland.
PMID: 31057735 DOI: 10.1039/c9md00093c
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.

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