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首页> 外文期刊>Chemistry: A European journal >Isolation, biological activity evaluation, structure elucidation, and total synthesis of eliamid: A novel complex i inhibitor
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Isolation, biological activity evaluation, structure elucidation, and total synthesis of eliamid: A novel complex i inhibitor

机译：lia虫酰胺的分离，生物活性评估，结构阐明和全合成：新型i复合物抑制剂

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摘要

Eliamid is a secondary metabolite isolated from two bacterial strains. This molecule features a linear polyketide backbone terminated by a tetramic acid amide moiety. Among other biological activities, eliamid shows a high and specific cytostatic action on human lymphoma and cervix carcinoma cell lines. The 2,4-anti relative configuration of the C-2,C-4-dimethyl substituted amide fragment was assigned by means of Breit's rule. The absolute configuration of all stereocenters was determined by a combination of degradation methods, structural similarity analysis and total synthesis. The stereogenic centers were introduced by vinylogous Mukaiyama aldol reaction and two consecutive Myers alkylations. The use of pentafluorophenyl ester as acylation agent allowed the efficient formation of tetramic acid amide. The longest linear sequence in the synthesis consist of 13 steps and proceeds with 12 % overall yield. Differential spectroscopy experiments with beef heart submitochondrial particles established that eliamid is a potent inhibitor of the NADH-ubiquinone oxidoreductase complex. Additionally, biosynthesis of eliamid was investigated by feeding experiments with 13C-labeled precursors. How valuable is Breit's rule? Isolation, biological activity profiling, structure elucidation and total synthesis of polyketide natural product eliamid are reported. This molecule is characterized by a tetramic acid amide fragment, which is rather rare among secondary metabolites isolated from myxobacteria.
机译：Eliamid是从两个细菌菌株中分离出来的次生代谢产物。该分子的特征是线性的聚酮化合物主链，其末端是一个四酰胺基。除其他生物活性外，依里亚酰胺对人淋巴瘤和子宫颈癌细胞系显示出高而特异性的细胞抑制作用。通过Breit法则指定了C-2，C-4-二甲基取代的酰胺片段的2，4-抗相对构型。所有立体中心的绝对构型由降解方法，结构相似性分析和全合成确定。通过乙烯基的Mukaiyama aldol反应和两个连续的Myers烷基化引入了立体异构中心。通过使用五氟苯基酯作为酰化剂，可以有效地形成四酰胺。合成中最长的线性序列包括13个步骤，总产率为12％。用牛肉心线粒体颗粒进行的差示光谱实验表明，依拉米胺是NADH-泛醌氧化还原酶复合物的有效抑制剂。此外，通过用13 C标记的前体进料实验研究了依里亚酰胺的生物合成。 Breit的规则有多有价值？据报道，聚酮化合物天然产物弹性体的分离，生物学活性分析，结构阐明和全合成。该分子的特征是四甲酰胺片段，在从粘菌分离的次生代谢产物中很少见。

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