Synthesis and biological characterization of arylomycin B antibiotics.
Synthesis and biological characterization of arylomycin B antibiotics.
复制标题
arylomycin B 抗生素的合成和生物学表征。
DOI：
10.1021/np200163g
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发表时间：
2011
影响因子：
5.1
通讯作者：
Romesberg,FloydE
中科院分区：
文献类型：
--
作者：
Roberts,TuckerC;Smith,PeterA;Romesberg,FloydE
抗生素实际上总是作为相关化合物的家族而被分离，但对所观察到的多样性背后的进化力量通常知之甚少，甚至不清楚它们是否都具有生物活性。芳基霉素类抗生素由三个相关家族组成，其通过保守核心支架的硝化、糖基化和羟基化来区分。以前，我们报道了A系列成员，芳基霉素A2，以及A系列衍生物芳基霉素C16的全合成，并表明两者都是对比以前认识到的更广泛的细菌的活性。本文报道了B系列类似物芳霉素B-C_（16）及其芳胺衍生物的全合成。虽然芳族胺失去了对所有测试细菌的活性，但B系列化合物显示出与A系列化合物相似的活性，除了它还获得了对重要病原体无乳链球菌的活性。
Antibiotics are virtually always isolated as families of related compounds, but the evolutionary forces underlying the observed diversity are generally poorly understood, and it is not even clear whether they are all expected to be biologically active. The arylomycin class of antibiotics is comprised of three related families that are differentiated by nitration, glycosylation, and hydroxylation of a conserved core scaffold. Previously, we reported the total synthesis of an A series member, arylomycin A2, as well as the A series derivative arylomycin C16and showed that both are active against a broader spectrum of bacteria than previously appreciated. We now report the total synthesis of a B series analogue, arylomycin B-C16, and its aromatic amine derivative. While the aromatic amine loses activity against all bacteria tested, the B series compound shows activities that are similar to the A series compounds, except that it also gains activity against the important pathogenStreptococcus agalactiae.