Department of Chemistry and Biochemistry, Georgia Southern University, Savannah, GA, USA.
Department of Chemistry and Biochemistry, Georgia Southern University, Savannah, GA, USA.
Bioorg Chem. 2019 Mar;84:394-398. doi: 10.1016/j.bioorg.2018.11.056. Epub 2018 Dec 1.
Peptide nucleic acids (PNA) are one of many synthetic mimics of DNA and RNA that have found applications as biological probes, as nano-scaffold components, and in diagnostics. In an effort to use PNA as constructs for cellular delivery we investigated the possibility of installing a biologically susceptible disulfide bond in the backbone of a PNA oligomer. Here we report the synthesis of a new abasic Fmoc monomer containing a disulfide bond that can be incorporated into a PNA oligomer (DS-PNA) using standard solid phase peptide synthesis. The disulfide bond survives cleavage from the resin and DS-PNA forms duplexes with complementary PNA oligomers. Initial studies aimed at determining if the disulfide bond is cleavable to reducing agents while in a duplex are explored using UV thermal analysis and HPLC.
肽核酸 (PNA) 是 DNA 和 RNA 的多种人工合成模拟物之一，已被用作生物探针、纳米支架成分和诊断试剂。为了将 PNA 用作细胞递运的构建体，我们研究了在 PNA 寡聚物骨架中引入生物易接近的二硫键的可能性。在这里，我们报告了一种新的含有二硫键的无碱基 Fmoc 单体的合成，该单体可以使用标准固相肽合成法掺入 PNA 寡聚物 (DS-PNA) 中。二硫键在从树脂上切割下来后仍然存在，并且 DS-PNA 与互补的 PNA 寡聚物形成双链体。使用 UV 热分析和 HPLC 探索了初始研究，以确定二硫键在双链体中是否可被还原剂切割。
