由阿泊拉霉素合成糖霉素及其核糖体选择性评估
Synthesis of saccharocin from apramycin and evaluation of its ribosomal selectivity.
作者信息
Sarpe Vikram A, Pirrone Michael G, Haldimann Klara, Hobbie Sven N, Vasella Andrea, Crich David
机构信息
Department of Chemistry , Wayne State University , 5101 Cass Avenue , Detroit , MI 48202 , USA . Email:
Institut für Medizinische Mikrobiologie , Universität Zürich , Gloriastrasse 30 , 8006 Zürich , Switzerland.
出版信息
Medchemcomm. 2019 Mar 13;10(4):554-558. doi: 10.1039/c9md00093c. eCollection 2019 Apr 1.
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.
摘要
我们描述了一种从阿泊拉霉素出发，通过区域选择性部分叠氮化，然后进行立体保持氧化脱氨，直接合成阿泊拉霉素生物合成前体糖霉素的方法。研究发现，糖霉素对细菌核糖体的抑制选择性远高于真核核糖体，这表明其作为阿泊拉霉素中的微量杂质，在后者作为临床候选药物的开发过程中应该不会产生问题。
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