Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity.
Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity.
复制标题
DOI：
10.1039/c9md00093c
复制
发表时间：
2019-04
期刊：
影响因子：
--
通讯作者：
Vikram A. Sarpe;Michael G. Pirrone;Klara Haldimann;S. Hobbie;A. Vasella;D. Crich
中科院分区：
文献类型：
--
作者：
Vikram A. Sarpe;Michael G. Pirrone;Klara Haldimann;S. Hobbie;A. Vasella;D. Crich
我们描述了一个简单的合成安普霉素的生物合成前体糖精从安普霉素的区域选择性部分叠氮化，然后立体保留氧化脱氨基。发现安普霉素在抑制细菌核糖体方面表现出优于真核核糖体的优异选择性，表明其作为安普霉素本身中的次要杂质的存在在后者作为临床候选药物的开发中不应成为问题。
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.