Switchable Protecting Strategy for Solid Phase Synthesis of DNA and RNA Interacting Nucleopeptides,The Journal of Organic Chemistry

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Switchable Protecting Strategy for Solid Phase Synthesis of DNA and RNA Interacting Nucleopeptides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2016-11-08 00:00:00 , DOI: 10.1021/acs.joc.6b01829
Maria Emilia Mercurio ₁ , Stefano Tomassi ₁ , Maria Gaglione ₁ , Rosita Russo ₁ , Angela Chambery ₁ , Stefania Lama ₂ , Paola Stiuso ₂ , Sandro Cosconati ₁ , Ettore Novellino ₃ , Salvatore Di Maro ₁ , Anna Messere ₁

Affiliation

Nucleopeptides are promising nucleic acid mimetics in which the peptide backbone bears nucleobases. They can recognize DNA and RNA targets modulating their biological functions. To date, the lack of an effective strategy for the synthesis of nucleopeptides prevents their evaluation for biological and biomedical applications. Herein, we describe an unprecedented approach that enables the synthesis of cationic both homo and heterosequence nucleopeptides wholly on solid support with high yield and purity. Spectroscopic studies indicate advantageous properties of the nucleopeptides in terms of binding, thermodynamic stability and sequence specific recognition. Biostability assay and laser scanning confocal microscopy analyses reveal that the nucleopeptides feature acceptable serum stability and ability to cross the cell membrane.

中文翻译：

固相合成DNA和RNA相互作用核肽的可切换保护策略

核酸肽是有希望的核酸模拟物，其中肽主链带有核碱基。他们可以识别调节其生物学功能的DNA和RNA靶标。迄今为止，缺乏合成核苷酸肽的有效策略阻止了其对生物和生物医学应用的评估。在这里，我们描述了一种前所未有的方法，该方法能够以高产率和纯度完全在固体支持物上合成阳离子同核苷酸和异核苷酸核苷酸。光谱研究表明核肽在结合，热力学稳定性和序列特异性识别方面的有利性质。生物稳定性测定和激光扫描共聚焦显微镜分析表明，核肽具有可接受的血清稳定性和穿过细胞膜的能力。

更新日期：2016-11-08

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