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Synthesis, self-assembly-behavior and biomolecular recognition properties of thyminyl dipeptides
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2020-01-01 , DOI: 10.1016/j.arabjc.2018.02.014
Giovanni N. Roviello , Giorgia Oliviero , Antonella Di Napoli , Nicola Borbone , Gennaro Piccialli

Abstract This article describes the synthesis of Thy-(Phe-Phe) and Thy-(Tyr-Tyr), two thymine-bearing dipeptides based on l -phenylalanine and l -tyrosine, the circular dichroism (CD), UV and dynamic light scattering (DLS) characterization of their self-assemblies, and a CD study of their interaction with nucleic acids (using homoadenine DNA and RNA) and serum proteins (utilizing BSA as a model protein). DLS studies, alongside with CD and UV investigations conducted on aqueous solutions of the derivatives under different concentration and temperature conditions, showed the formation of extensive molecular architectures with hydrodynamic mean diameters higher than 300 nm, with Thy-(Tyr-Tyr) forming at pH = 7.5 particularly large and stable networks, involving multiple units, connected by H-bonding, aromatic and hydrophobic interactions. Finally, the findings of our study suggested that Thy-(Phe-Phe) and Thy-(Tyr-Tyr), very stable in human serum, were able to bind BSA protein altering its secondary structure.

中文翻译:

胸腺嘧啶二肽的合成、自组装行为和生物分子识别特性

摘要 本文描述了 Thy-(Phe-Phe) 和 Thy-(Tyr-Tyr) 的合成,这两种基于 l-苯丙氨酸和 l-酪氨酸的胸腺嘧啶二肽、圆二色性 (CD)、紫外线和动态光散射(DLS) 表征它们的自组装,以及它们与核酸(使用高腺嘌呤 DNA 和 RNA)和血清蛋白(使用 BSA 作为模型蛋白)相互作用的 CD 研究。DLS 研究以及在不同浓度和温度条件下对衍生物水溶液进行的 CD 和 UV 研究表明,形成了流体力学平均直径高于 300 nm 的广泛分子结构,在 pH 值下形成了 Thy-(Tyr-Tyr) = 7.5 特别大且稳定的网络,涉及多个单元,通过氢键、芳香族和疏水性相互作用连接。最后,
更新日期:2020-01-01
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