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首页> 外文期刊>Bulletin of the Chemical Society of Japan >Total syntheses of sterically locked phycocyanobilin derivatives bearing a 15Z-anti or a 15E-anti CD-ring component
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Total syntheses of sterically locked phycocyanobilin derivatives bearing a 15Z-anti or a 15E-anti CD-ring component

机译:带有15Z-抗或15E-抗CD环成分的空间锁定藻蓝蛋白衍生物的总合成

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摘要

Total syntheses of sterically locked phycocyanobilin derivatives with a 15Z-anti or a 15E-anti CD-ring component were performed toward elucidation of the stereochemistry and function of the chromophore in phytochromes. In the course of the construction of a sterically locked 15E-anti CD-ring component employing 5-tosylpyrrolin-2-one derivatives as the D-ring, the Ts group was found to be rearranged under acidic conditions to give a mixture of regioisomers, both of which could be transformed into the same CD-ring precursor via detosylation with a base followed by Wittig-like coupling reaction. In addition, a sterically locked 15E-anti biliverdin derivative was also synthesized.
机译:为了阐明植物色素中的生色团的立体化学和功能,进行了具有15Z-抗或15E-抗CD-环组分的空间锁定的藻蓝蛋白衍生物的总合成。在使用5-甲苯磺酰基吡咯啉-2-一衍生物作为D环的立体锁定15E-抗CD环组件的构建过程中,发现Ts基团在酸性条件下发生了重排,从而形成了区域异构体的混合物,两者都可以通过与碱基解毒,然后进行类似Wittig的偶联反应,转化为相同的CD环前体。另外,还合成了空间锁定的15E-抗胆绿素衍生物。

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