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Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity


Sarpe, Vikram A; Pirrone, Michael G; Haldimann, Klara; Hobbie, Sven N; Vasella, Andrea; Crich, David (2019). Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity. MedChemComm, 10(4):554-558.

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > Institute of Medical Microbiology
Dewey Decimal Classification:570 Life sciences; biology
610 Medicine & health
Scopus Subject Areas:Life Sciences > Biochemistry
Life Sciences > Molecular Medicine
Life Sciences > Pharmacology
Life Sciences > Pharmaceutical Science
Life Sciences > Drug Discovery
Physical Sciences > Organic Chemistry
Language:English
Date:1 April 2019
Deposited On:13 Feb 2020 15:57
Last Modified:29 Jul 2020 14:23
Publisher:Royal Society of Chemistry
ISSN:2040-2503
OA Status:Closed
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/c9md00093c
PubMed ID:31057735

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