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首页> 外文期刊>Chemistry: A European journal >Selectfluor and NFSI exo-Glycal Fluorination Strategies Applied to the Enhancement of the Binding Affinity of Galactofuranosyltransferase GlfT2 Inhibitors
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Selectfluor and NFSI exo-Glycal Fluorination Strategies Applied to the Enhancement of the Binding Affinity of Galactofuranosyltransferase GlfT2 Inhibitors

机译：Selectfluor和NFSI外糖基氟化策略用于增强半乳糖呋喃糖基转移酶GlfT2抑制剂的结合亲和力

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摘要

Two complementary methods for the synthesis of fluorinated exo-glycals have been developed, for which previously no general reaction had been available. First, a Selectfluor-mediated fluorination was optimized after detailed analysis of all the reaction parameters. A dramatic effect of molecular sieves on the course of the reaction was observed. The reaction was generalized with a set of biologically relevant furanosides and pyranosides. A second direct approach involving carbanionic chemistry and the use of N-fluorobenzenesulfonimide (NFSI) was performed and this method gave better diastereoselectivities. Assignment of the Z/E configuration of all the fluorinated exo-glycals was achieved based on the results of HOESY experiments. Furthermore, fluorinated exo-glycal analogues of UDP-galactofuranose were prepared and assayed against GlfT2, which is a key enzyme involved in the cell-wall biosynthesis of major pathogens. The fluorinated exo-glycals proved to be potent inhibitors as compared with a series of C-glycosidic analogues of UDP-Galf, thus demonstrating the double beneficial effect of the exocyclic enol ether functionality and the fluorine atom.
机译：已经开发了两种合成氟化外糖的互补方法，以前尚无通用反应。首先，在详细分析所有反应参数后，优化Selectfluor介导的氟化反应。观察到分子筛对反应过程的显着影响。反应用一组生物学上相关的呋喃糖苷和吡喃糖苷泛化。进行了涉及碳负离子化学和使用N-氟苯磺酰亚胺（NFSI）的第二种直接方法，该方法具有更好的非对映选择性。基于HOESY实验的结果，实现了所有氟化外糖的Z / E构型的分配。此外，制备了UDP-半乳糖呋喃糖的氟化外糖类似物并针对GlfT2进行了测定，GlfT2是参与主要病原体细胞壁生物合成的关键酶。与一系列UDP-Galf的C-糖苷类似物相比，氟化的外糖被证明是有效的抑制剂，因此证明了外环烯醇醚官能度和氟原子的双重有益作用。

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